MiMeDB: Showing metabocard for Cholesterol (MMDBc0000020)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:27:27 UTC

Update Date

2022-08-30 23:03:47 UTC

Metabolite ID

MMDBc0000020

Metabolite Identification

Common Name

Cholesterol

Description

Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50% of the lipid in the membrane or 60-80% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with cholesterol has always been specifically with cholesterol transport patterns, not total cholesterol per se. For example, total cholesterol can be low, yet made up primarily of small LDL and small HDL particles and atheroma growth rates are high. In contrast, however, if LDL particle number is low (mostly large particles) and a large percentage of the HDL particles are large (HDL is actively reverse transporting cholesterol), then atheroma growth rates are usually low, even negative, for any given total cholesterol concentration. These effects are further complicated by the relative concentration of asymmetric dimethylarginine (ADMA) in the endothelium since ADMA down-regulates production of nitric oxide, a relaxant of the endothelium. Thus, high levels of ADMA, associated with highly oxidized levels of LDL, pose a heightened risk factor for vascular disease. Chronically high levels of cholesterol are associated with at least five inborn errors of metabolism, including cerebrotendinous xanthomatosis, cholesteryl ester storage disease, congenital lipoid adrenal hyperplasia, hypercholesterolemia, and Zellweger syndrome. In chronically high levels, cholesterol can function as an atherogen (causes atherosclerosis and cardiovascular disease). Specifically, chronically high levels (from diet or from genetic predisposition or from diseases such as hyperlipidemia) of cholesterol and cholesterol esters lead to an excess of low-density lipoprotein (LDL) particles. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. Resistin, a protein secreted by fat tissue, has been shown to increase the production of LDL in human liver cells and also degrades LDL receptors in the liver. As a result, the liver is less able to clear cholesterol from the bloodstream. Resistin accelerates the accumulation of LDL in arteries, increasing the risk of heart disease. Cholesterol is considered to be practically insoluble (in water) and basic.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309272007322D          

 32 35  0  0  0  0            999 V2000
 9999.976110000.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8380 9999.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6955 9997.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5507 9998.1599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2634 9999.3952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9761 9998.1599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1240 9998.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4095 9998.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4095 9997.7403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1240 9997.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8385 9997.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8385 9998.5654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.263810000.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5493 9999.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5493 9998.9868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2638 9998.5744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5507 9997.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2652 9997.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9783 9999.8118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9783 9998.9868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7629 9998.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2477 9999.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.762910000.0668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.762910000.8918    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.478610001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192210000.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.907910001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.623610000.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337310001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.623610000.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049310001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.478610000.4793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 15  4  1  6  0  0  0
 18 16  1  0  0  0  0
 16  5  1  1  0  0  0
  9  3  1  1  0  0  0
 12  2  1  1  0  0  0
 15 12  1  0  0  0  0
 11 17  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 32  1  6  0  0  0
 24 25  1  0  0  0  0
 24 31  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 16 20  1  0  0  0  0
 20  6  1  6  0  0  0
 13 19  1  0  0  0  0
 19  1  1  1  0  0  0
M  END

HMDB0000067
     RDKit          3D
Cholesterol
 74 77  0  0  0  0  0  0  0  0999 V2000
    6.3404   -0.4853   -2.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5104    0.5474   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8984    1.9007   -1.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0699    0.2257   -1.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306    1.1860   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2999    1.2050    0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503   -0.1074    1.2620 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2950    0.1498    2.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7705   -0.7322    0.9221 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6395   -2.1097    1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589   -2.3605    1.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987   -1.3642    0.9032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7963   -0.9706    0.9406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7818   -2.1185    1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220   -1.4967    0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4126   -0.4414    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8017    0.0752    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2980    0.0525   -1.1429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4683    0.7782   -1.2208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3281    0.5472   -2.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283    0.0601   -2.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4062    0.2574   -0.5692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4744    1.7636   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0628   -0.3211   -0.4317 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8855    0.5523   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138    0.9621    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4801   -0.1350    1.2821 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2899   -0.0181    2.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157   -1.3949   -2.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6617   -0.0879   -3.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2421   -0.7740   -1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8186    0.5156   -0.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9989    1.9705   -2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795    2.7399   -1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4762    2.0006   -2.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889   -0.8250   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827    0.3365   -2.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    0.9554   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3898    2.2008   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3397    1.5837    0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456    1.9789    1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8617   -0.8000    0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029    0.9544    3.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3543    0.5713    2.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4019   -0.7634    3.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676   -0.9938   -0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066   -2.9220    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233   -2.1579    2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592   -2.3347    2.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1329   -3.3851    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534   -1.6136   -0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224   -0.2119    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144   -2.8723    0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5934   -2.6383    1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9126   -1.9825    1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8991    1.0613    0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4704   -0.6089    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5134   -1.0272   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3809    1.5508   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3281    1.6510   -2.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6933    0.1568   -3.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2759    0.7133   -2.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7958   -1.0133   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486    2.2288   -1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879    2.1191    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5706    2.0238   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9957   -1.1963   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1426    0.0554   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721    1.4878   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9039    1.4440    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5194    1.8027    0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057   -0.7145    3.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185    1.0136    3.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211   -0.4007    3.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 13 52  1  1
 14 53  1  0
 14 54  1  0
 15 55  1  0
 17 56  1  0
 17 57  1  0
 18 58  1  6
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  END


  Mrv1652309272007322D          

 32 35  0  0  0  0            999 V2000
 9999.976110000.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8380 9999.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6955 9997.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5507 9998.1599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2634 9999.3952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9761 9998.1599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1240 9998.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4095 9998.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4095 9997.7403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1240 9997.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8385 9997.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8385 9998.5654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.263810000.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5493 9999.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5493 9998.9868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2638 9998.5744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5507 9997.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2652 9997.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9783 9999.8118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9783 9998.9868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7629 9998.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2477 9999.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.762910000.0668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.762910000.8918    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.478610001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192210000.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.907910001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.623610000.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337310001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.623610000.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049310001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.478610000.4793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 15  4  1  6  0  0  0
 18 16  1  0  0  0  0
 16  5  1  1  0  0  0
  9  3  1  1  0  0  0
 12  2  1  1  0  0  0
 15 12  1  0  0  0  0
 11 17  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 32  1  6  0  0  0
 24 25  1  0  0  0  0
 24 31  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 16 20  1  0  0  0  0
 20  6  1  6  0  0  0
 13 19  1  0  0  0  0
 19  1  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000020

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
HVYWMOMLDIMFJA-DPAQBDIFSA-N

> <FORMULA>
C27H46O

> <MOLECULAR_WEIGHT>
386.6535

> <EXACT_MASS>
386.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.641441246997644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
7.02

> <JCHEM_LOGP>
7.112889030666665

> <ALOGPS_LOGS>
-7.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
120.61649999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.79e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000067
     RDKit          3D
Cholesterol
 74 77  0  0  0  0  0  0  0  0999 V2000
    6.3404   -0.4853   -2.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5104    0.5474   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8984    1.9007   -1.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0699    0.2257   -1.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306    1.1860   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2999    1.2050    0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503   -0.1074    1.2620 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2950    0.1498    2.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7705   -0.7322    0.9221 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6395   -2.1097    1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589   -2.3605    1.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987   -1.3642    0.9032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7963   -0.9706    0.9406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7818   -2.1185    1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220   -1.4967    0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4126   -0.4414    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8017    0.0752    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2980    0.0525   -1.1429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4683    0.7782   -1.2208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3281    0.5472   -2.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283    0.0601   -2.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4062    0.2574   -0.5692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4744    1.7636   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0628   -0.3211   -0.4317 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8855    0.5523   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138    0.9621    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4801   -0.1350    1.2821 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2899   -0.0181    2.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157   -1.3949   -2.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6617   -0.0879   -3.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2421   -0.7740   -1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8186    0.5156   -0.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9989    1.9705   -2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795    2.7399   -1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4762    2.0006   -2.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889   -0.8250   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827    0.3365   -2.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    0.9554   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3898    2.2008   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3397    1.5837    0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456    1.9789    1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8617   -0.8000    0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029    0.9544    3.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3543    0.5713    2.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4019   -0.7634    3.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676   -0.9938   -0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066   -2.9220    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233   -2.1579    2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592   -2.3347    2.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1329   -3.3851    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534   -1.6136   -0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224   -0.2119    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144   -2.8723    0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5934   -2.6383    1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9126   -1.9825    1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8991    1.0613    0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4704   -0.6089    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5134   -1.0272   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3809    1.5508   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3281    1.6510   -2.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6933    0.1568   -3.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2759    0.7133   -2.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7958   -1.0133   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486    2.2288   -1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879    2.1191    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5706    2.0238   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9957   -1.1963   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1426    0.0554   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721    1.4878   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9039    1.4440    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5194    1.8027    0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057   -0.7145    3.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185    1.0136    3.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211   -0.4007    3.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 13 52  1  1
 14 53  1  0
 14 54  1  0
 15 55  1  0
 17 56  1  0
 17 57  1  0
 18 58  1  6
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.6228667.865   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.6318665.538   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.6328661.672   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.9618663.232   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8665.2928665.538   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.6228663.232   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8661.2988664.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.9648663.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8659.9648662.449   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.2988661.679   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.6328662.449   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.6328663.989   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2928667.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.9598666.316   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9598664.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.2928664.006   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.9618661.679   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.2958662.449   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.6268666.315   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.6268664.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.0918664.300   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.9968665.545   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0918666.791   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.0918668.331   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.4278669.101   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8670.7598668.331   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8672.0958669.101   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8673.4318668.331   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8674.7638669.101   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8673.4318666.791   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8666.7598669.101   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0    8669.4278667.561   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2   12                                                            
CONECT    3    9                                                            
CONECT    4   15                                                            
CONECT    5   16                                                            
CONECT    6   20                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    3                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12    7   11    2   15                                             
CONECT   13   14   19                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    4   12                                             
CONECT   16   15   18    5   20                                             
CONECT   17   18   11                                                       
CONECT   18   17   16                                                       
CONECT   19   20   23   13    1                                             
CONECT   20   19   21   16    6                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   32   19   22                                             
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   24                                                            
CONECT   32   23                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0000067
HETATM    1  C1  UNL     1       6.340  -0.485  -2.104  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.510   0.547  -1.359  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.898   1.901  -1.930  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.070   0.226  -1.599  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.131   1.186  -0.908  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.300   1.205   0.577  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.050  -0.107   1.262  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.295   0.150   2.732  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.771  -0.732   0.922  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.639  -2.110   1.642  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.159  -2.360   1.809  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.399  -1.364   0.903  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.796  -0.971   0.941  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.782  -2.119   1.025  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.122  -1.497   0.958  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.413  -0.441   0.254  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.802   0.075   0.280  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.298   0.052  -1.143  1.00  0.00           C  
HETATM   19  O1  UNL     1      -7.468   0.778  -1.221  1.00  0.00           O  
HETATM   20  C19 UNL     1      -5.328   0.547  -2.157  1.00  0.00           C  
HETATM   21  C20 UNL     1      -3.928   0.060  -2.016  1.00  0.00           C  
HETATM   22  C21 UNL     1      -3.406   0.257  -0.569  1.00  0.00           C  
HETATM   23  C22 UNL     1      -3.474   1.764  -0.379  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.063  -0.321  -0.432  1.00  0.00           C  
HETATM   25  C24 UNL     1      -0.886   0.552  -0.720  1.00  0.00           C  
HETATM   26  C25 UNL     1      -0.114   0.962   0.519  1.00  0.00           C  
HETATM   27  C26 UNL     1       0.480  -0.135   1.282  1.00  0.00           C  
HETATM   28  C27 UNL     1       0.290  -0.018   2.785  1.00  0.00           C  
HETATM   29  H1  UNL     1       5.716  -1.395  -2.344  1.00  0.00           H  
HETATM   30  H2  UNL     1       6.662  -0.088  -3.091  1.00  0.00           H  
HETATM   31  H3  UNL     1       7.242  -0.774  -1.530  1.00  0.00           H  
HETATM   32  H4  UNL     1       5.819   0.516  -0.315  1.00  0.00           H  
HETATM   33  H5  UNL     1       6.999   1.971  -2.052  1.00  0.00           H  
HETATM   34  H6  UNL     1       5.579   2.740  -1.301  1.00  0.00           H  
HETATM   35  H7  UNL     1       5.476   2.001  -2.957  1.00  0.00           H  
HETATM   36  H8  UNL     1       3.889  -0.825  -1.352  1.00  0.00           H  
HETATM   37  H9  UNL     1       3.883   0.337  -2.693  1.00  0.00           H  
HETATM   38  H10 UNL     1       2.132   0.955  -1.253  1.00  0.00           H  
HETATM   39  H11 UNL     1       3.390   2.201  -1.277  1.00  0.00           H  
HETATM   40  H12 UNL     1       4.340   1.584   0.814  1.00  0.00           H  
HETATM   41  H13 UNL     1       2.646   1.979   1.005  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.862  -0.800   0.933  1.00  0.00           H  
HETATM   43  H15 UNL     1       2.703   0.954   3.166  1.00  0.00           H  
HETATM   44  H16 UNL     1       4.354   0.571   2.743  1.00  0.00           H  
HETATM   45  H17 UNL     1       3.402  -0.763   3.344  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.768  -0.994  -0.155  1.00  0.00           H  
HETATM   47  H19 UNL     1       2.007  -2.922   0.943  1.00  0.00           H  
HETATM   48  H20 UNL     1       2.223  -2.158   2.551  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.159  -2.335   2.859  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.133  -3.385   1.444  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.053  -1.614  -0.140  1.00  0.00           H  
HETATM   52  H24 UNL     1      -2.122  -0.212   1.668  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.614  -2.872   0.215  1.00  0.00           H  
HETATM   54  H26 UNL     1      -2.593  -2.638   1.983  1.00  0.00           H  
HETATM   55  H27 UNL     1      -4.913  -1.983   1.556  1.00  0.00           H  
HETATM   56  H28 UNL     1      -5.899   1.061   0.767  1.00  0.00           H  
HETATM   57  H29 UNL     1      -6.470  -0.609   0.854  1.00  0.00           H  
HETATM   58  H30 UNL     1      -6.513  -1.027  -1.381  1.00  0.00           H  
HETATM   59  H31 UNL     1      -7.381   1.551  -0.582  1.00  0.00           H  
HETATM   60  H32 UNL     1      -5.328   1.651  -2.289  1.00  0.00           H  
HETATM   61  H33 UNL     1      -5.693   0.157  -3.154  1.00  0.00           H  
HETATM   62  H34 UNL     1      -3.276   0.713  -2.644  1.00  0.00           H  
HETATM   63  H35 UNL     1      -3.796  -1.013  -2.227  1.00  0.00           H  
HETATM   64  H36 UNL     1      -3.049   2.229  -1.289  1.00  0.00           H  
HETATM   65  H37 UNL     1      -3.088   2.119   0.571  1.00  0.00           H  
HETATM   66  H38 UNL     1      -4.571   2.024  -0.439  1.00  0.00           H  
HETATM   67  H39 UNL     1      -1.996  -1.196  -1.146  1.00  0.00           H  
HETATM   68  H40 UNL     1      -0.143   0.055  -1.388  1.00  0.00           H  
HETATM   69  H41 UNL     1      -1.172   1.488  -1.235  1.00  0.00           H  
HETATM   70  H42 UNL     1      -0.904   1.444   1.185  1.00  0.00           H  
HETATM   71  H43 UNL     1       0.519   1.803   0.221  1.00  0.00           H  
HETATM   72  H44 UNL     1       1.006  -0.714   3.259  1.00  0.00           H  
HETATM   73  H45 UNL     1       0.319   1.014   3.147  1.00  0.00           H  
HETATM   74  H46 UNL     1      -0.721  -0.401   3.115  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4   32
CONECT    3   33   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8    9   42
CONECT    8   43   44   45
CONECT    9   10   27   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   27   51
CONECT   13   14   24   52
CONECT   14   15   53   54
CONECT   15   16   16   55
CONECT   16   17   22
CONECT   17   18   56   57
CONECT   18   19   20   58
CONECT   19   59
CONECT   20   21   60   61
CONECT   21   22   62   63
CONECT   22   23   24
CONECT   23   64   65   66
CONECT   24   25   67
CONECT   25   26   68   69
CONECT   26   27   70   71
CONECT   27   28
CONECT   28   72   73   74
END

HMDB0000067
     RDKit          3D
Cholesterol
 74 77  0  0  0  0  0  0  0  0999 V2000
    6.3404   -0.4853   -2.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5104    0.5474   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8984    1.9007   -1.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0699    0.2257   -1.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306    1.1860   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2999    1.2050    0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503   -0.1074    1.2620 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2950    0.1498    2.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7705   -0.7322    0.9221 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6395   -2.1097    1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589   -2.3605    1.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987   -1.3642    0.9032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7963   -0.9706    0.9406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7818   -2.1185    1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220   -1.4967    0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4126   -0.4414    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8017    0.0752    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2980    0.0525   -1.1429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4683    0.7782   -1.2208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3281    0.5472   -2.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283    0.0601   -2.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4062    0.2574   -0.5692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4744    1.7636   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0628   -0.3211   -0.4317 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8855    0.5523   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138    0.9621    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4801   -0.1350    1.2821 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2899   -0.0181    2.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157   -1.3949   -2.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6617   -0.0879   -3.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2421   -0.7740   -1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8186    0.5156   -0.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9989    1.9705   -2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795    2.7399   -1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4762    2.0006   -2.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889   -0.8250   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827    0.3365   -2.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    0.9554   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3898    2.2008   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3397    1.5837    0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456    1.9789    1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8617   -0.8000    0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029    0.9544    3.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3543    0.5713    2.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4019   -0.7634    3.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676   -0.9938   -0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066   -2.9220    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233   -2.1579    2.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592   -2.3347    2.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1329   -3.3851    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534   -1.6136   -0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224   -0.2119    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144   -2.8723    0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5934   -2.6383    1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9126   -1.9825    1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8991    1.0613    0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4704   -0.6089    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5134   -1.0272   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3809    1.5508   -0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3281    1.6510   -2.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6933    0.1568   -3.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2759    0.7133   -2.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7958   -1.0133   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486    2.2288   -1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879    2.1191    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5706    2.0238   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9957   -1.1963   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1426    0.0554   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721    1.4878   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9039    1.4440    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5194    1.8027    0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057   -0.7145    3.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185    1.0136    3.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211   -0.4007    3.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 13 52  1  1
 14 53  1  0
 14 54  1  0
 15 55  1  0
 17 56  1  0
 17 57  1  0
 18 58  1  6
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
M  END

Synonyms

Value	Source
(3beta,14beta,17alpha)-Cholest-5-en-3-ol	ChEBI
Cholest-5-en-3beta-ol	ChEBI
Cholesterin	ChEBI
(3b,14b,17a)-Cholest-5-en-3-ol	Generator
(3Β,14β,17α)-cholest-5-en-3-ol	Generator
Cholest-5-en-3b-ol	Generator
Cholest-5-en-3β-ol	Generator
(3Β)-cholest-5-en-3-ol	HMDB
(3beta)-Cholest-5-en-3-ol	HMDB
3Β-hydroxycholest-5-ene	HMDB
3beta-Hydroxycholest-5-ene	HMDB
5:6-Cholesten-3β-ol	HMDB
5:6-Cholesten-3beta-ol	HMDB
(-)-Cholesterol	HMDB
Cholesterine	HMDB
Cholesterol base H	HMDB
Cholesteryl alcohol	HMDB
Cholestrin	HMDB
Cholestrol	HMDB
Cordulan	HMDB
Dastar	HMDB
Dusoline	HMDB
Dusoran	HMDB
Dythol	HMDB
Fancol CH	HMDB
Hydrocerin	HMDB
Kathro	HMDB
Lanol	HMDB
Super hartolan	HMDB
Tegolan	HMDB
Cholesterol	HMDB
delta5-Cholesten-3beta-ol	PhytoBank
Δ5-Cholesten-3β-ol	PhytoBank

Molecular Formula

C₂₇H₄₆O

Average Mass

386.6535

Monoisotopic Mass

386.354866094

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

57-88-5

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

HVYWMOMLDIMFJA-DPAQBDIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Cholesterol
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:16113 )
3beta-sterol (CHEBI:16113 )
cholestane (C00187 )
Cholesterol and derivatives (C00187 )
Cholestane and derivatives (C00187 )
Cholesterol and derivatives (LMST01010001 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.8e-05 g/L	ALOGPS
logP	7.02	ALOGPS
logP	7.11	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.62 m³·mol⁻¹	ChemAxon
Polarizability	50.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004i-3911000000-52f5261007adc218f8f8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052b-2932000000-1667c83d002043a59fff	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000l-9527000000-5529a262047f5369c9c1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0mkr-2954000000-60e7d1f5973e4de33dec	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014i-1009000000-e82b8e23dedb45ce70e6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-056v-2900000000-04687c9f19ff52ba4654	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i3-1109000000-8cd386b595bd5151c5a2	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0006-3104900000-698223f49da0b0c1cf81	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, positive	splash10-052u-0690000000-36b4aea6637bdf069b5d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-014i-3639000000-18a9275beb9bae48c1d7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-014j-4934000000-f755ada933cfcf53c303	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0002-5921000000-e7d43c825b9f6d45e679	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0532-5910000000-ce90c49b7429a03a65da	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-05nb-8900000000-2e8913fec7126b5b2a62	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0apl-9600000000-3096c7a78c3dd2e6a538	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 50V, positive	splash10-067l-9400000000-1b57543b4cd0a05b9b3f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 60V, positive	splash10-0aru-9300000000-45a29b76dfefce3f01ca	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0009000000-dccd68f70545aeac4fab	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05p9-3149000000-7f25daf2b709c7e0d177	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c00-6269000000-5333d0216e01a3e43367	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-dc853b29b9e884bbb03b	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-09d9608700564a6fef78	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ldi-1009000000-96f6e67651380e1c959e	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-2d9cbc8b5b1fa392fb9b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abj-9173000000-9086873e4b65db1ced63	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8920000000-bd94fa538afb75d04765	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-c037f2d2f217e99b79ac	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-7de5154056e69e7319e1	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0009000000-96c53273291d4857bde4	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-7922000000-36e8a5e1a77d2e71d1d1	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2014-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Golgi apparatus
Lysosome
Membrane
Mitochondria

Biospecimen Locations

All Tissues
Bile
Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Prostate
Saliva
Urine

Tissue Locations

All Tissues
Placenta
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191743	Phosphatidylcholine-sterol acyltransferase	Enzyme	P04180	Homo sapiens
MMDBp0191897	Lysosomal acid lipase/cholesteryl ester hydrolase	Enzyme	P38571	Homo sapiens
MMDBp0191911	Bile salt-activated lipase	Unknown	P19835	Homo sapiens
MMDBp0192023	Sulfotransferase family cytosolic 2B member 1	Enzyme	O00204	Homo sapiens
MMDBp0192150	Steryl-sulfatase	Unknown	P08842	Homo sapiens
MMDBp0192156	Sterol O-acyltransferase 2	Enzyme	O75908	Homo sapiens
MMDBp0192158	Cholesterol 7-alpha-monooxygenase	Unknown	P22680	Homo sapiens
MMDBp0192159	Sterol O-acyltransferase 1	Enzyme	P35610	Homo sapiens
MMDBp0192195	7-dehydrocholesterol reductase	Enzyme	Q9UBM7	Homo sapiens
MMDBp0192362	Cholesterol side-chain cleavage enzyme, mitochondrial	Unknown	P05108	Homo sapiens
MMDBp0192648	Sterol 26-hydroxylase, mitochondrial	Unknown	Q02318	Homo sapiens
MMDBp0193162	ATP-binding cassette sub-family A member 1	Unknown	O95477	Homo sapiens
MMDBp0193164	Apolipoprotein A-I	Enzyme	P02647	Homo sapiens
MMDBp0193337	Delta(24)-sterol reductase	Unknown	Q15392	Homo sapiens
MMDBp0193419	Multidrug resistance protein 1	Transporter	P08183	Homo sapiens
MMDBp0193475	ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	Homo sapiens
MMDBp0193596	Nuclear receptor ROR-alpha	Enzyme	P35398	Homo sapiens
MMDBp0193781	Cholesterol 25-hydroxylase	Unknown	O95992	Homo sapiens
MMDBp0193989	Cholesterol 24-hydroxylase	Unknown	Q9Y6A2	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Bloch Pathway (Cholesterol Biosynthesis)
Kandutsch-Russell Pathway (Cholesterol Biosynthesis)
Aldosterone from Steroidogenesis

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000463	Cholesterol	Water	Cholesterol 25-hydroxylase	Cholesterol 25-Hydroxylase	VMH	30371894
MMDBr0000481	Cholesterol	Cholesterol sulfate	Sulfotransferase family, cytosolic, 1a, phenol-preferring, member 3	Steroid Sulfotransferase	VMH	12145317 9799594
MMDBr0000482	Cholesterol	Cholesterol	Star-related lipid transfer (start) domain containing 3	Cholesterol Intracellular Transport	VMH	12070139 12370263 12770731
MMDBr0000483	Cholesterol	Cholesterol	Not Available	Cholesterol Intracellular Transport	VMH	12370263 12770731
MMDBr0000484	Cholesterol	Cholesterol	Not Available	Cholesterol Intracellular Transport	VMH	12370263 12770731
MMDBr0000485	Adenosine triphosphate	ADP	Atp-binding cassette, sub-family a (abc1), member 1	Cholesterol Efflux (ATP Depedent), Golgi Apparatus	VMH	10655069 12600718
MMDBr0000669	Desmosterol	Cholesterol	24-dehydrocholesterol reductase	24-Dehydrocholesterol Reductase [Precursor]	VMH	17984220 19520779 19520780
MMDBr0000670	7-Dehydrocholesterol	Cholesterol	7-dehydrocholesterol reductase	7-Dehydrocholesterol Reductase	VMH	15670717
MMDBr0001840	Cholesterol	4-Methylpentanal	Cytochrome p450, family 11, subfamily a, polypeptide 1	Cytochrome P450 11A1, Mitochondrial [Precursor]	VMH	16232916
MMDBr0001857	Cholesterol	Water	Cytochrome p450, family 27, subfamily a, polypeptide 1	Cytochrome P450 27	VMH	30371894
MMDBr0001873	Cholesterol	Water	Cytochrome p450, family 46, subfamily a, polypeptide 1	Cytochrome P450, Family 46, Subfamily A, Polypeptide 1	VMH	30371894
MMDBr0001879	Cholesterol	Water	Cytochrome p450, family 7, subfamily a, polypeptide 1	Cytochrome P450, Family 7, Subfamily A, Polypeptide 1	VMH	30371894
MMDBr0002764	Adenosine triphosphate	ADP	Atp-binding cassette, sub-family g (white), member 5	ATP-Binding Cassette (ABC) Tcdb:3.A.1.204.5	VMH	15209530
MMDBr0002833	Cholesterol	Cholesterol	Not Available	Vesicular Transport	VMH	10772724 12856181
MMDBr0002834	Cholesterol	Cholesterol	Not Available	Vesicular Transport	VMH	10772724 12856181
MMDBr0002835	Cholesterol	Cholesterol	Not Available	Vesicular Transport	VMH	10772724 12856181
MMDBr0002871	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Sterol O-Acyltransferase	VMH	2760547 7822296 9242919
MMDBr0002872	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Sterol O-Acyltransferase	VMH	2760547 7822296 9242919
MMDBr0002873	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Sterol O-Acyltransferase	VMH	2760547 7822296 9242919
MMDBr0002874	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Sterol O-Acyltransferase	VMH	2760547 7822296 9242919
MMDBr0002875	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Sterol O-Acyltransferase	VMH	2760547 7822296 9242919
MMDBr0002876	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Sterol O-Acyltransferase	VMH	2760547 7822296 9242919
MMDBr0002877	Arachidonyl-CoA	Coenzyme A	Sterol o-acyltransferase 1	Sterol O-Acyltransferase	VMH	2760547 7822296 9242919
MMDBr0002878	Water	Cholesterol	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002879	Water	Cholesterol	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002880	Water	Cholesterol	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002881	Water	Cholesterol	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002882	Water	Cholesterol	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002883	Water	Cholesterol	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002884	Water	Cholesterol	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002885	Water	Cholesterol	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002886	Water	Cholesterol	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002887	Water	Cholesterol	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002888	Water	Arachidonic acid	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0002889	Water	Arachidonic acid	Carboxyl ester lipase	Sterol Esterase	VMH	11230747 8112342
MMDBr0003953	Cholesterol sulfate	Cholesterol	Steroid sulfatase (microsomal), isozyme s	Steryl-Sulfatase	VMH	10049998 1606923
MMDBr0003954	Cholesterol sulfate	Cholesterol	Steroid sulfatase (microsomal), isozyme s	Steryl-Sulfatase	VMH	10049998 1606923
MMDBr0003955	Cholesterol sulfate	Cholesterol	Steroid sulfatase (microsomal), isozyme s	Steryl-Sulfatase	VMH	10049998 1606923
MMDBr0003956	Cholesterol sulfate	Cholesterol	Steroid sulfatase (microsomal), isozyme s	Steryl-Sulfatase	VMH	10049998 1606923
MMDBr0004539	Desmosterol	Cholesterol	Not Available	RE3129N	VMH	11111101
MMDBr0005433	Cholesterol	Cholesterol	Not Available	Transport of Cholesterol into the Cytosol	VMH	30371894
MMDBr0005450	Desmosterol	Cholesterol	24-dehydrocholesterol reductase	Desmosterol Reductase	VMH	30371894
MMDBr0005689	Adenosine triphosphate	ADP	Atp-binding cassette, sub-family a (abc1), member 1	Cholesterol Efflux (ATP Depedent)	VMH	30371894
MMDBr0005724	Water	Cholesterol	Carboxyl ester lipase	Hydrolysis of 1-Gamma-Linolenoyl-Cholesterol, Cholesterol-Ester (18:3, Delta 6, 9, 12)	VMH	30371894
MMDBr0005725	Water	Cholesterol	Carboxyl ester lipase	Hydrolysis of 1-Linoleoyl-Cholesterol, Cholesterol-Ester (18:2, Delta 9, 12)	VMH	30371894
MMDBr0005726	Water	Cholesterol	Carboxyl ester lipase	Hydrolysis of 1-Vaccenoyl-Cholesterol, Cholesterol-Ester (18:1, Delta 11)	VMH	30371894
MMDBr0005727	Water	Cholesterol	Carboxyl ester lipase	Hydrolysis of 1-Timnodnoyl-Cholesterol, Cholesterol-Ester (20:5, Delta 5, 8, 11, 14, 17)	VMH	30371894
MMDBr0005728	Water	Arachidonic acid	Carboxyl ester lipase	Hydrolysis of Cholesteryl Arachidonate, Cholesterol-Ester (20:4, Delta 5, 8, 11, 14)	VMH	30371894
MMDBr0005729	Water	Cholesterol	Carboxyl ester lipase	Hydrolysis of Cholesteryl Docosahexanoate, Cholesterol-Ester (22:6, Delta 4, 7, 10, 13, 16, 19)	VMH	30371894
MMDBr0008425	Cholesterol	Cholesterol	Not Available	Cholesterol uptake (extracellular)	VMH	30371894
MMDBr0009537	Desmosterol	Cholesterol	24-dehydrocholesterol reductase	Cholesterol:NADP+ Delta24-Oxidoreductase	VMH	30371894
MMDBr0009547	7-Dehydrocholesterol	Cholesterol	7-dehydrocholesterol reductase	Cholesterol:NADP+ Delta7-Oxidoreductase	VMH	30371894
MMDBr0009566	Cholesterol	Water	Cytochrome p450, family 46, subfamily a, polypeptide 1	Cholesterol 24-Hydroxylase	VMH	30371894
MMDBr0009597	Cholesterol	Water	Cholesterol 25-hydroxylase	Cholesterol 25-Hydroxylase	VMH	30371894
MMDBr0009598	Cholesterol	Water	Cholesterol 25-hydroxylase	Cholesterol 25-Hydroxylase	VMH	30371894
MMDBr0009605	Cholesterol	Cholesterol	High density lipoprotein binding protein	HMR_1916	VMH	30371894
MMDBr0009606	Cholesterol	Water	Coenzyme q6 monooxygenase	HMR_1927	VMH	30371894
MMDBr0010201	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010202	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010203	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010204	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010205	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010206	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010207	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010208	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010209	Water	Arachidic acid	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010210	Water	11Z-Eicosenoic acid	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010211	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010212	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010213	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010214	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010215	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010216	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010217	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010218	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010219	Water	(7Z,10Z,13Z,16Z)-docosatetraenoate	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010220	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010221	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010222	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010223	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010224	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010225	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010226	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010227	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010228	Eicosanoyl-CoA	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010229	11Z-Eicosenoyl Coenzyme A	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010230	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010231	13Z-docosenoyl-CoA	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010232	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010233	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010234	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010235	Cervonyl Coenzyme A	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010236	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010237	Adrenyl coenzyme A	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010238	(11Z,14Z)-Icosadienoyl Coenzyme A	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010239	Cholesterol	Coenzyme A	Sterol o-acyltransferase 1	Acyl Coenzyme A:Cholesterol O-Acyltransferase	VMH	30371894
MMDBr0010240	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010241	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010242	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010243	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010244	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010245	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010246	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010247	Water	Arachidic acid	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010248	Water	11Z-Eicosenoic acid	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010249	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010250	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010251	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010252	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010253	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010254	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010255	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010256	Water	(7Z,10Z,13Z,16Z)-docosatetraenoate	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0010257	Water	Cholesterol	Carboxyl ester lipase	Steryl-Ester Acylhydrolase	VMH	30371894
MMDBr0012636	Cholesterol	5beta-Coprostanol	Not Available	Cholesterol to coprotanol reduction, cytoplasmic	VMH	30371894
MMDBr0012689	Cholesterol	5beta-Coprostanol	Not Available	Cholesterol to coprostanol reduction, extracellular	VMH	30371894
MMDBr0014404	Cholesterol	7-Dehydrocholesterol	Probable 7-dehydrocholesterol reductase	Reduction	RHEA	34755880
MMDBr0015274	CE(18:1(9Z))	(9Z)-octadecenoic acid	Triacylglycerol lipase 4	Lipid (ester bond) hydrolysis	RHEA	34755880
MMDBr0015275	CE(18:1(9Z))	(9Z)-octadecenoic acid	Triacylglycerol lipase 4	Lipid (ester bond) hydrolysis	RHEA	34755880
MMDBr0015936	Cholesterol	27-Hydroxycholesterol	Methyl-branched lipid omega-hydroxylase	Hydroxylation; Oxygenation	RHEA	34755880
MMDBr0015937	Cholesterol	27-Hydroxycholesterol	Methyl-branched lipid omega-hydroxylase	Hydroxylation; Oxygenation	RHEA	34755880
MMDBr0024884	Oxygen	Hydrogen peroxide	Cholesterol oxidase	Oxidation	RHEA	34755880
MMDBr0024885	Oxygen	Hydrogen peroxide	Cholesterol oxidase	Oxidation	RHEA	34755880
MMDBr0024940	Cholesterol	Hydrogen Ion	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase	Reduction	RHEA	34755880
MMDBr0024941	Cholesterol	Hydrogen Ion	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase	Reduction	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Abetalipoproteinemia		Association	Human Blood	HMDB	2944375
Acute myelogenous leukemia		Association	Human Blood	HMDB	11463495
Cerebrotendinous xanthomatosis	Increased	Association	Human Blood	HMDB	23001091
Cerebrotendinous xanthomatosis	Increased	Association	Human Blood	HMDB	16445943
Cholelithiasis	Increased	Association	Human Bile	HMDB	8591852
Cholesteryl ester storage disease		Association	Human Blood	HMDB	11380065
Cholesteryl ester storage disease		Association	Human Blood	HMDB	18478331
Cholesteryl ester storage disease		Association	Human Blood	HMDB	23485521
Cystinosis		Association	Human Blood	HMDB	17699259
Cystinosis		Association	Human Blood	HMDB	3276734
Gallbladder disease	Slight Increase	Association	Human Bile	HMDB	8591852
Gallbladder disease	Increased	Association	Human Bile	HMDB	8462368
Hypercholesterolemia		Association	Human Blood	HMDB	3422148
Hyperlipoproteinemia	Decreased	Association	Human Blood	HMDB	23402469
Hyperlipoproteinemia		Association	Human Blood	HMDB	7752915
Multiple sclerosis	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	15576852
Oculocerebrorenal syndrome	Slight Increase	Association	Human Blood	HMDB	2017228
Primary hypomagnesemia	Increased	Association	Human Blood	HMDB	10337938
Smith-lemli-opitz syndrome		Association	Human Cerebrospinal Fluid (CSF)	HMDB	9266395
Smith-lemli-opitz syndrome		Association	Human Blood	HMDB	9266395
Stomach cancer		Association	Human Bile	HMDB	9027647
Cholesteryl ester storage disease		Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Cholesteryl ester storage disease		Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Cystinosis		Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	2	Human appendix biopsy; Human stool; Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	17	Human feces; Human stool; Human ; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Viruses/Bamfordvirae	Nucleocytoviricota	1
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown
Bacteria	Actinobacteria	1	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	4060				uM	Infant (0-1 year old)	Male	3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency	HMDB	29030856
Human Blood	Detected and Quantified	2190				uM	Adult (>18 years old)	Male	Abetalipoproteinemia	HMDB	2944375
Human Blood	Detected and Quantified	3200.0		2600.0	4100.0	uM	Adult (>18 years old)	Both	Acute myelogenous leukemia (AML)	HMDB	11463495
Human Blood	Detected and Quantified	4250.0585	658.471			uM	Adult (>18 years old)	Both	Apolipoprotein C-II deficiency	HMDB	7138621
Human Blood	Detected and Quantified	4319.113				uM	Adult (>18 years old)	Male	27-hydroxylase deficiency	HMDB	23001091
Human Blood	Detected and Quantified	5715.712				uM	Adult (>18 years old)	Male	27-hydroxylase deficiency	HMDB	16445943
Human Bile	Detected and Quantified	13900		13100	14700	uM	Adult (>18 years old)	Both	Cholesterol stones	HMDB	8591852
Human Blood	Detected and Quantified	5896.753				uM	Adult (>18 years old)	Not Specified	Cholesteryl ester storage disease	HMDB	11380065
Human Blood	Detected and Quantified	8198.555				uM	Children (1-13 years old)	Not Specified	Cholesteryl ester storage disease	HMDB	11380065
Human Blood	Detected and Quantified			2689.747	16035.0288	uM	Children (1-13 years old)	Both	Cholesteryl ester storage disease	HMDB	18478331
Human Blood	Detected and Quantified	2844.924		2689.747	16035.0288	uM	Children (1-13 years old)	Both	Cholesteryl ester storage disease	HMDB	23485521
Human Blood	Detected and Quantified	4474.29				uM	Children (1-13 years old)	Male	Chondrodysplasia punctata, X-linked dominant	HMDB	12503102
Human Blood	Detected and Quantified	>5172.590				uM	Adult (>18 years old)	Both	Cystinosis	HMDB	17699259
Human Blood	Detected and Quantified	4836.372	1215.559			uM	Children (1-13 years old)	Both	Cystinosis	HMDB	3276734
Human Blood	Detected and Quantified	4189.798				uM	Children (1-13 years old)	Male	Desmosterolosis	HMDB	12457401
Human Blood	Detected and Quantified	1293.147				uM	Newborn (0-30 days old)	Male	Donohue Syndrome	HMDB	26871809
Human Blood	Detected and Quantified	4920	3640			uM	Children (1-13 years old)	Male	Duchenne Muscular Dystrophy	HMDB	19787747
Human Blood	Detected and Quantified	4980	2730			uM	Children (1-13 years old)	Male	Duchenne Muscular Dystrophy	HMDB	19787747
Human Blood	Detected and Quantified	5060		4390	6260	uM	Adult (>18 years old)	Both	Familial partial lipodystrophy	HMDB	28754454
Human Bile	Detected and Quantified	13100		10900	15300	uM	Adult (>18 years old)	Both	Gallstone disease	HMDB	8591852
Human Bile	Detected and Quantified	16700		14100	19300	uM	Adult (>18 years old)	Both	Gallstone disease	HMDB	8462368
Human Blood	Detected and Quantified	5700.0		5200.0	6200.0	uM	Adult (>18 years old)	Both	Hypercholesterolemia	HMDB	3422148
Human Blood	Detected and Quantified	7725.263	1629.366			uM	Children (1-13 years old)	Both	Hypercholesterolemia, familial	HMDB	4363406
Human Blood	Detected and Quantified	<5172.590				uM	Adult (>18 years old)	Both	Hyperlipidemia	HMDB	23402469
Human Blood	Detected and Quantified	2680	1850			uM	Adult (>18 years old)		Familial lipoprotein lipase deficiency	HMDB	7752915
Human Blood	Detected and Quantified	4100				uM	Children (1-13 years old)	Male	Lathosterolosis	HMDB	24142275
Human Blood	Detected and Quantified			2190	2940	uM	Adult (>18 years old)	Both	Lecithin:cholesterol Acyltransferase Deficiency	HMDB	16051254
Human Blood	Detected and Quantified	4991.549				uM	Infant (0-1 year old)	Female	Leptin Deficiency or Dysfunction	HMDB	10486419
Human Blood	Detected and Quantified	4750		4210	5930	uM	Adult (>18 years old)	Both	Lipodystrophy	HMDB	28754454
Human Blood	Detected and Quantified	4580		3740	6040	uM	Adult (>18 years old)	Both	Lipodystrophy, Congenital Generalized	HMDB	28754454
Human Cerebrospinal fluid (csf)	Detected and Quantified	10.9	2.7			uM	Adult (>18 years old)	Both	Multiple Sclerosis	HMDB	15576852
Human Blood	Detected and Quantified	5720		3830	10030	uM	Children (1-13 years old)	Not Specified	Oculocerebrorenal Syndrome of Lowe	HMDB	2017228
Human Blood	Detected and Quantified	4630		4030	5460	uM	Adult (>18 years old)	Both	Partial lipodystrophy	HMDB	28754454
Human Blood	Detected and Quantified	4629.468				uM	Adult (>18 years old)	Male	Primary Hypomagnesemia	HMDB	10337938
Human Blood	Detected and Quantified			2198.351	2405.254	uM	Adolescent (13-18 years old)	Female	SC4MOL deficiency	HMDB	21285510
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.1				uM	Infant (0-1 year old)	Both	Smith-Lemli-Opitz syndrome	HMDB	9266395
Human Blood	Detected and Quantified	400				uM	Infant (0-1 year old)	Both	Smith-Lemli-Opitz syndrome	HMDB	9266395
Human Bile	Detected and Quantified	15110		9860	20360	uM	Adult (>18 years old)	Both	Stomach cancer	HMDB	9027647
Human Saliva	Detected and Quantified	<1.00				uM	Adult (>18 years old)	Both	Normal	HMDB	15179829
Human Blood	Detected and Quantified	<4400				uM	Not Specified	Not Specified	Normal	HMDB	29030856
Human Blood	Detected and Quantified	<5172.590				uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	10486419
Human Blood	Detected and Quantified	<5172.590				uM	Children (1-13 years old)	Not Specified	Normal	HMDB	12457401
Human Blood	Detected and Quantified	>6207.108				uM	Adult (>18 years old)	Both	Normal	HMDB	23402469
Human Bile	Detected and Quantified	11500		10000	13000	uM	Adult (>18 years old)	Both	Normal	HMDB	8462368
Human Blood	Detected and Quantified	1230	250			uM	Adult (>18 years old)		Normal	HMDB	7752915
Human Blood	Detected and Quantified	1920	1290			uM	Children (1-13 years old)	Male	Normal	HMDB	19787747
Human Blood	Detected and Quantified			3080	5400	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	2017228
Human Blood	Detected and Quantified			3620.813	4551.879	uM	Adolescent (13-18 years old)	Not Specified	Normal	HMDB	21285510
Human Blood	Detected and Quantified	3760	98			uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	3801.854		2870.787	4732.920	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	12503102
Human Blood	Detected and Quantified	3879.442	905.203			uM	Children (1 - 13 years old)	Female	Normal	HMDB	227694
Human Blood	Detected and Quantified			390	570	uM	Adult (>18 years old)	Female	Normal	HMDB	8787802
Human Blood	Detected and Quantified			3900	6500	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	2944375
Human Cerebrospinal fluid (csf)	Detected and Quantified	4.30		3.90	4.70	uM	Adult (>18 years old)	Both	Normal	HMDB	9266395
Human Blood	Detected and Quantified	4008.757	750.0255			uM	Children (1 - 13 years old)	Male	Normal	HMDB	227694
Human Blood	Detected and Quantified			430	610	uM	Adult (>18 years old)	Male	Normal	HMDB	8787802
Human Blood	Detected and Quantified	4409.633	788.820			uM	Adult (>18 years old)	Both	Normal	HMDB	7138621
Human Blood	Detected and Quantified	4750		4220	5230	uM	Adult (>18 years old)	Both	Normal	HMDB	28754454
Human Blood	Detected and Quantified	4850	1020			uM	Adult (>18 years old)	Male	Normal	HMDB	28278231
Human Blood	Detected and Quantified	4960	1170			uM	Adult (>18 years old)	Female	Normal	HMDB	28278231
Human Blood	Detected and Quantified	5700.0		4500.0	6700.0	uM	Adult (>18 years old)	Both	Normal	HMDB	11463495
Human Cerebrospinal fluid (csf)	Detected and Quantified	8.32		7.88	8.76	uM	Adult (>18 years old)	Both	Normal	HMDB	15576852
Human Blood	Detected and Quantified	820	9			uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	4141.0		3105.0	5176.0	uM	Adult (>18 years old)	Both	Cholesteryl ester storage disease	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	9317.8		7764.8	10870.8	uM	Children (1-13 years old)	Both	Cholesteryl ester storage disease	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	8000.0		6000.0	10000.0	uM	Children (1-13 years old)	Both	Cystinosis	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified			1086.24	2819.062	uM	Newborn (0 - <14 days old)	Male	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			1189.70	3232.87	uM	Newborn (0 - <14 days old)	Female	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			1655.23	6129.52	uM	Infant (15 days - <1 year old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			2896.65	5379.49	uM	Children (1 - <19 years old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified	5000.0		4500.0	5500.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified			0	5193.280	uM	Adult (>18 years old)	Both	Normal	HMDB	Vancouver Coastal Health Lab (http://www.vch.ca/Locations-Services/result?res_id=601)
Human Blood	Detected and Quantified			0.0	5200	uM	Adult (>18 years old)	Female	Normal	HMDB	Vancouver Coastal Health Lab (http://www.vch.ca/Locations-Services/result?res_id=601)
Human Blood	Detected and Quantified			0.0	5200	uM	Adult (>18 years old)	Male	Normal	HMDB	Vancouver Coastal Health Lab (http://www.vch.ca/Locations-Services/result?res_id=601)
Human All tissues	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	1268322
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	22944170
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22007635
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24789758
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	28157703
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000067

DrugBank ID

DB04540

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013269

KNApSAcK ID

C00003648

Chemspider ID

Not Available

KEGG Compound ID

C00187

BioCyc ID

CHOLESTEROL

BiGG ID

Not Available

Wikipedia Link

Cholesterol

METLIN ID

Not Available

PubChem Compound

5997

PDB ID

Not Available

ChEBI ID

16113

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bjorkhem I, Heverin M, Leoni V, Meaney S, Diczfalusy U: Oxysterols and Alzheimer's disease. Acta Neurol Scand Suppl. 2006;185:43-9. doi: 10.1111/j.1600-0404.2006.00684.x. [PubMed:16866910 ]
Ellis D, Lloyd C, Becker DJ, Forrest KY, Orchard TJ: The changing course of diabetic nephropathy: low-density lipoprotein cholesterol and blood pressure correlate with regression of proteinuria. Am J Kidney Dis. 1996 Jun;27(6):809-18. doi: 10.1016/s0272-6386(96)90518-1. [PubMed:8651245 ]
Gil'miiarova FN, Pervova IuV, Radomskaia VM, Gergel' NI, Tarasova SV: [Levels of unified metabolites and thyroid hormones in blood and oral fluid of children with minimal brain dysfunction]. Biomed Khim. 2004 Mar-Apr;50(2):204-10. [PubMed:15179829 ]
Thelen KM, Falkai P, Bayer TA, Lutjohann D: Cholesterol synthesis rate in human hippocampus declines with aging. Neurosci Lett. 2006 Jul 31;403(1-2):15-9. doi: 10.1016/j.neulet.2006.04.034. Epub 2006 May 15. [PubMed:16701946 ]
Schillaci G, Pirro M, Ronti T, Gemelli F, Pucci G, Innocente S, Porcellati C, Mannarino E: Prognostic impact of prolonged ventricular repolarization in hypertension. Arch Intern Med. 2006 Apr 24;166(8):909-13. doi: 10.1001/archinte.166.8.909. [PubMed:16636218 ]
Higashijima H, Ichimiya H, Nakano T, Yamashita H, Kuroki S, Satoh H, Chijiiwa K, Tanaka M: Deconjugation of bilirubin accelerates coprecipitation of cholesterol, fatty acids, and mucin in human bile--in vitro study. J Gastroenterol. 1996 Dec;31(6):828-35. doi: 10.1007/BF02358610. [PubMed:9027647 ]
Proksch GJ, Bonderman DP: Use of a cholesterol-rich bovine lipoprotein to enhance cholesterol concentrations in the preparation of serum control materials. Clin Chem. 1976 Aug;22(8):1302-5. [PubMed:985740 ]
van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. doi: 10.1023/a:1005355026186. [PubMed:9266395 ]
Sanchez E, Fernandez-D'Pool J: [Liver function in patients exposed to a toluene in a hydrocarbon processing plant]. Invest Clin. 1996 Dec;37(4):255-70. [PubMed:9004852 ]
Mizuno S, Tazuma S, Kajiyama G: Stabilization of biliary lipid particles by ursodeoxycholic acid. Prolonged nucleation time in human gallbladder bile. Dig Dis Sci. 1993 Apr;38(4):684-93. doi: 10.1007/BF01316801. [PubMed:8462368 ]
Bookman ID, Pham J, Guindi M, Heathcote EJ: Distinguishing nonalcoholic steatohepatitis from fatty liver: serum-free fatty acids, insulin resistance, and serum lipoproteins. Liver Int. 2006 Jun;26(5):566-71. doi: 10.1111/j.1478-3231.2006.01256.x. [PubMed:16762001 ]
Nigg C, Gutzwiller F: [Cholesterol: blood level and control by Swiss physicians]. Schweiz Med Wochenschr. 1995 Feb 25;125(8):355-60. [PubMed:7709184 ]
Winocour PH, Durrington PN, Bhatnagar D, Ishola M, Mackness M, Arrol S: Influence of early diabetic nephropathy on very low density lipoprotein (VLDL), intermediate density lipoprotein (IDL), and low density lipoprotein (LDL) composition. Atherosclerosis. 1991 Jul;89(1):49-57. doi: 10.1016/0021-9150(91)90006-o. [PubMed:1772471 ]
Hoffmann G, Gibson KM, Brandt IK, Bader PI, Wappner RS, Sweetman L: Mevalonic aciduria--an inborn error of cholesterol and nonsterol isoprene biosynthesis. N Engl J Med. 1986 Jun 19;314(25):1610-4. doi: 10.1056/NEJM198606193142504. [PubMed:3012338 ]
Markuszewski L, Rosiak M, Golanski J, Rysz J, Spychalska M, Watala C: Reduced blood platelet sensitivity to aspirin in coronary artery disease: are dyslipidaemia and inflammatory states possible factors predisposing to sub-optimal platelet response to aspirin? Basic Clin Pharmacol Toxicol. 2006 May;98(5):503-9. doi: 10.1111/j.1742-7843.2006.pto_343.x. [PubMed:16635110 ]
Miettinen TE, Kesaniemi YA, Gylling H, Jarvinen H, Silvennoinen E, Miettinen TA: Noncholesterol sterols in bile and stones of patients with cholesterol and pigment stones. Hepatology. 1996 Feb;23(2):274-80. doi: 10.1002/hep.510230212. [PubMed:8591852 ]
Leoni V, Lutjohann D, Masterman T: Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res. 2005 Feb;46(2):191-5. doi: 10.1194/jlr.C400005-JLR200. Epub 2004 Dec 1. [PubMed:15576852 ]
D'Amico G, Gentile MG: Effect of dietary manipulation on the lipid abnormalities and urinary protein loss in nephrotic patients. Miner Electrolyte Metab. 1992;18(2-5):203-6. [PubMed:1465059 ]
Pak CH, Oleneva VA, Agadzhanov SA: [Dietetic aspects of preventing urolithiasis in patients with gout and uric acid diathesis]. Vopr Pitan. 1985 Jan-Feb;(1):21-4. [PubMed:3885567 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. doi: 10.1194/jlr.R400004-JLR200. [PubMed:15254070 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..

Showing metabocard for Cholesterol (MMDBc0000020)

MOL for #<Metabolite:0x00007f5a942316d0>

3D MOL for #<Metabolite:0x00007f5a942316d0>

3D SDF for #<Metabolite:0x00007f5a942316d0>

3D-SDF for #<Metabolite:0x00007f5a942316d0>

PDB for #<Metabolite:0x00007f5a942316d0>

3D PDB for #<Metabolite:0x00007f5a942316d0>

SMILES for #<Metabolite:0x00007f5a942316d0>

INCHI for #<Metabolite:0x00007f5a942316d0>

Structure for #<Metabolite:0x00007f5a942316d0>

3D Structure for #<Metabolite:0x00007f5a942316d0>