MiMeDB: Showing metabocard for beta-Sitosterol (MMDBc0052894)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:08:21 UTC

Update Date

2024-04-30 20:44:09 UTC

Metabolite ID

MMDBc0052894

Metabolite Identification

Common Name

beta-Sitosterol

Description

beta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. Phytosterols are plant sterols found in foods such as oils, nuts, and vegetables. Phytosterols, in the same way as cholesterol, contain a double bond and are susceptible to oxidation, and are characterized by anti-carcinogenic and anti-atherogenic properties (PMID:13129445 , 11432711 ). beta-Sitosterol is a phytopharmacological extract containing a mixture of phytosterols, with smaller amounts of other sterols, bonded with glucosides. These phytosterols are commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea. The purported active constituent is termed beta-sitosterol. Additionally, the quantity of beta-sitosterol-beta-D-glucoside is often reported. Although the exact mechanism of action of beta-sitosterols is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism). Compared with placebo, beta-sitosterol improved urinary symptom scores and flow measures (PMID:10368239 ). A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. This finding indicates that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID:14652381 ). beta-Sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID:12579296 ).

Structure

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


  Mrv1652309272007292D          

 34 37  0  0  0  0            999 V2000
 9999.976210000.6420    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
 9995.6956 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
 9999.2635 9999.3952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 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
 9999.263810000.2244    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
10001.2478 9999.3993    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  2  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
10002.907910002.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.623610002.5418    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 34  1  6  0  0  0
 24 25  1  0  0  0  0
 24 33  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
 27 31  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 31 32  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

HMDB0000852
     RDKit          3D
beta-Sitosterol
 80 83  0  0  0  0  0  0  0  0999 V2000
   -6.6627    1.8491   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3580    1.9523    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218    1.1671    0.7913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9248    1.6484    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5683    1.0972    0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3407   -0.2931   -0.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5795   -0.4037   -1.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -0.8837    0.2466 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9685   -2.2933   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700   -2.4480   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668   -1.4481    0.0270 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5189   -1.0160   -0.4197 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4449   -2.2291   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855   -1.6616   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511   -0.4357   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5481   -0.0177   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2773    0.3309    0.2994 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5748    0.7359    0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5005    1.4630    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196    1.0167    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044    0.5474    0.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9926    1.6973   -0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -0.1665    0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1057    0.6910    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.7498    0.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332   -0.2272   -0.0940 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3904    0.3717   -1.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4283   -0.2456    1.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8867   -1.0858   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6331   -0.2439    2.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6061    1.2375   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9995    2.8718   -1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8732    1.5707   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1226    3.0276    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2383    1.6867    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    1.5998    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0708    1.7280   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    2.7893    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313    1.8290   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143    1.1075    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809   -0.9513    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -0.9810   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7713    0.6184   -2.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607   -0.9180   -2.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -0.9864    1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204   -2.5398   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -3.0545    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536   -3.4793   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528   -2.3241   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261   -1.7930    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5468   -0.4781   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -2.7282    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -2.8961   -1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4647   -2.3360   -1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0550   -0.7714   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188    0.8902   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -0.5169    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2208   -0.0344    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5163    2.3828    0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0407    1.6849    1.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2056    0.1582    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    1.8714    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1326    2.3030   -0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7675    1.2712   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9004    2.3071   -0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -0.9081    1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1151    0.4675    2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5426    1.7387    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068    0.6522    1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661    1.7735    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4285    0.9887   -1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045   -0.3325   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2602    1.0968   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6636   -0.7424    1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7288   -0.7063   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9740   -1.3852   -0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3480   -2.0804   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5902    0.6144    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5639   -0.2532    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6174   -1.1659    2.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  1
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  1
 12 51  1  6
 13 52  1  0
 13 53  1  0
 14 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  1
 18 58  1  0
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 22 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  1
 24 67  1  0
 24 68  1  0
 25 69  1  0
 25 70  1  0
 27 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 30 80  1  0
M  END


  Mrv1652309272007292D          

 34 37  0  0  0  0            999 V2000
 9999.976210000.6420    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
 9995.6956 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
 9999.2635 9999.3952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 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
 9999.263810000.2244    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
10001.2478 9999.3993    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  2  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
10002.907910002.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.623610002.5418    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 34  1  6  0  0  0
 24 25  1  0  0  0  0
 24 33  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
 27 31  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 31 32  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>
MMDBc0052894

> <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)CC[C@@H](CC)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
KZJWDPNRJALLNS-VJSFXXLFSA-N

> <FORMULA>
C29H50O

> <MOLECULAR_WEIGHT>
414.718

> <EXACT_MASS>
414.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.21112448234584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.27

> <JCHEM_LOGP>
7.844476792000004

> <ALOGPS_LOGS>
-7.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <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>
129.76609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e-05 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000852
     RDKit          3D
beta-Sitosterol
 80 83  0  0  0  0  0  0  0  0999 V2000
   -6.6627    1.8491   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3580    1.9523    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218    1.1671    0.7913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9248    1.6484    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5683    1.0972    0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3407   -0.2931   -0.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5795   -0.4037   -1.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -0.8837    0.2466 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9685   -2.2933   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700   -2.4480   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668   -1.4481    0.0270 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5189   -1.0160   -0.4197 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4449   -2.2291   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855   -1.6616   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511   -0.4357   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5481   -0.0177   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2773    0.3309    0.2994 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5748    0.7359    0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5005    1.4630    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196    1.0167    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044    0.5474    0.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9926    1.6973   -0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -0.1665    0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1057    0.6910    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.7498    0.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332   -0.2272   -0.0940 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3904    0.3717   -1.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4283   -0.2456    1.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8867   -1.0858   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6331   -0.2439    2.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6061    1.2375   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9995    2.8718   -1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8732    1.5707   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1226    3.0276    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2383    1.6867    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    1.5998    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0708    1.7280   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    2.7893    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313    1.8290   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143    1.1075    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809   -0.9513    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -0.9810   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7713    0.6184   -2.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607   -0.9180   -2.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -0.9864    1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204   -2.5398   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -3.0545    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536   -3.4793   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528   -2.3241   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261   -1.7930    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5468   -0.4781   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -2.7282    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -2.8961   -1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4647   -2.3360   -1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0550   -0.7714   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188    0.8902   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -0.5169    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2208   -0.0344    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5163    2.3828    0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0407    1.6849    1.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2056    0.1582    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    1.8714    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1326    2.3030   -0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7675    1.2712   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9004    2.3071   -0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -0.9081    1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1151    0.4675    2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5426    1.7387    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068    0.6522    1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661    1.7735    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4285    0.9887   -1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045   -0.3325   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2602    1.0968   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6636   -0.7424    1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7288   -0.7063   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9740   -1.3852   -0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3480   -2.0804   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5902    0.6144    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5639   -0.2532    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6174   -1.1659    2.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  1
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  1
 12 51  1  6
 13 52  1  0
 13 53  1  0
 14 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  1
 18 58  1  0
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 22 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  1
 24 67  1  0
 24 68  1  0
 25 69  1  0
 25 70  1  0
 27 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 30 80  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    8665.2928667.086   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    8672.0958670.641   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8673.4318671.411   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8666.7598669.101   0.000  0.00  0.00           C+0
HETATM   34  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   34   19   22                                             
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32                                                       
CONECT   32   31                                                            
CONECT   33   24                                                            
CONECT   34   23                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0000852
HETATM    1  C1  UNL     1      -6.663   1.849  -1.125  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.358   1.952   0.309  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.122   1.167   0.791  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.925   1.648   0.107  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.568   1.097   0.321  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.341  -0.293  -0.169  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.579  -0.404  -1.671  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.034  -0.884   0.247  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.968  -2.293  -0.307  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.470  -2.448  -0.820  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.167  -1.448   0.027  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.519  -1.016  -0.420  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.445  -2.229  -0.612  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.785  -1.662  -0.915  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.151  -0.436  -0.573  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.548  -0.018  -0.957  1.00  0.00           C  
HETATM   17  C17 UNL     1       7.277   0.331   0.299  1.00  0.00           C  
HETATM   18  O1  UNL     1       8.575   0.736   0.097  1.00  0.00           O  
HETATM   19  C18 UNL     1       6.500   1.463   0.965  1.00  0.00           C  
HETATM   20  C19 UNL     1       5.120   1.017   1.345  1.00  0.00           C  
HETATM   21  C20 UNL     1       4.304   0.547   0.148  1.00  0.00           C  
HETATM   22  C21 UNL     1       3.993   1.697  -0.773  1.00  0.00           C  
HETATM   23  C22 UNL     1       3.088  -0.167   0.678  1.00  0.00           C  
HETATM   24  C23 UNL     1       2.106   0.691   1.384  1.00  0.00           C  
HETATM   25  C24 UNL     1       0.716   0.750   0.939  1.00  0.00           C  
HETATM   26  C25 UNL     1       0.233  -0.227  -0.094  1.00  0.00           C  
HETATM   27  C26 UNL     1       0.390   0.372  -1.439  1.00  0.00           C  
HETATM   28  C27 UNL     1      -5.428  -0.246   1.025  1.00  0.00           C  
HETATM   29  C28 UNL     1      -5.887  -1.086  -0.104  1.00  0.00           C  
HETATM   30  C29 UNL     1      -6.633  -0.244   2.034  1.00  0.00           C  
HETATM   31  H1  UNL     1      -7.606   1.238  -1.301  1.00  0.00           H  
HETATM   32  H2  UNL     1      -6.999   2.872  -1.484  1.00  0.00           H  
HETATM   33  H3  UNL     1      -5.873   1.571  -1.815  1.00  0.00           H  
HETATM   34  H4  UNL     1      -6.123   3.028   0.558  1.00  0.00           H  
HETATM   35  H5  UNL     1      -7.238   1.687   0.911  1.00  0.00           H  
HETATM   36  H6  UNL     1      -5.038   1.600   1.863  1.00  0.00           H  
HETATM   37  H7  UNL     1      -4.071   1.728  -1.025  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.888   2.789   0.347  1.00  0.00           H  
HETATM   39  H9  UNL     1      -1.831   1.829  -0.111  1.00  0.00           H  
HETATM   40  H10 UNL     1      -2.314   1.107   1.426  1.00  0.00           H  
HETATM   41  H11 UNL     1      -3.081  -0.951   0.274  1.00  0.00           H  
HETATM   42  H12 UNL     1      -3.496  -0.981  -1.922  1.00  0.00           H  
HETATM   43  H13 UNL     1      -2.771   0.618  -2.116  1.00  0.00           H  
HETATM   44  H14 UNL     1      -1.761  -0.918  -2.209  1.00  0.00           H  
HETATM   45  H15 UNL     1      -1.076  -0.986   1.368  1.00  0.00           H  
HETATM   46  H16 UNL     1      -1.720  -2.540  -1.045  1.00  0.00           H  
HETATM   47  H17 UNL     1      -1.063  -3.055   0.502  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.854  -3.479  -0.598  1.00  0.00           H  
HETATM   49  H19 UNL     1       0.553  -2.324  -1.896  1.00  0.00           H  
HETATM   50  H20 UNL     1       1.226  -1.793   1.062  1.00  0.00           H  
HETATM   51  H21 UNL     1       2.547  -0.478  -1.374  1.00  0.00           H  
HETATM   52  H22 UNL     1       3.518  -2.728   0.382  1.00  0.00           H  
HETATM   53  H23 UNL     1       3.075  -2.896  -1.407  1.00  0.00           H  
HETATM   54  H24 UNL     1       5.465  -2.336  -1.449  1.00  0.00           H  
HETATM   55  H25 UNL     1       7.055  -0.771  -1.560  1.00  0.00           H  
HETATM   56  H26 UNL     1       6.419   0.890  -1.581  1.00  0.00           H  
HETATM   57  H27 UNL     1       7.282  -0.517   1.009  1.00  0.00           H  
HETATM   58  H28 UNL     1       9.221  -0.034   0.090  1.00  0.00           H  
HETATM   59  H29 UNL     1       6.516   2.383   0.364  1.00  0.00           H  
HETATM   60  H30 UNL     1       7.041   1.685   1.906  1.00  0.00           H  
HETATM   61  H31 UNL     1       5.206   0.158   2.035  1.00  0.00           H  
HETATM   62  H32 UNL     1       4.617   1.871   1.841  1.00  0.00           H  
HETATM   63  H33 UNL     1       3.133   2.303  -0.491  1.00  0.00           H  
HETATM   64  H34 UNL     1       3.767   1.271  -1.791  1.00  0.00           H  
HETATM   65  H35 UNL     1       4.900   2.307  -0.878  1.00  0.00           H  
HETATM   66  H36 UNL     1       3.507  -0.908   1.426  1.00  0.00           H  
HETATM   67  H37 UNL     1       2.115   0.468   2.496  1.00  0.00           H  
HETATM   68  H38 UNL     1       2.543   1.739   1.371  1.00  0.00           H  
HETATM   69  H39 UNL     1      -0.007   0.652   1.806  1.00  0.00           H  
HETATM   70  H40 UNL     1       0.466   1.773   0.524  1.00  0.00           H  
HETATM   71  H41 UNL     1      -0.429   0.989  -1.796  1.00  0.00           H  
HETATM   72  H42 UNL     1       0.705  -0.333  -2.238  1.00  0.00           H  
HETATM   73  H43 UNL     1       1.260   1.097  -1.382  1.00  0.00           H  
HETATM   74  H44 UNL     1      -4.664  -0.742   1.624  1.00  0.00           H  
HETATM   75  H45 UNL     1      -5.729  -0.706  -1.107  1.00  0.00           H  
HETATM   76  H46 UNL     1      -6.974  -1.385  -0.057  1.00  0.00           H  
HETATM   77  H47 UNL     1      -5.348  -2.080  -0.062  1.00  0.00           H  
HETATM   78  H48 UNL     1      -6.590   0.614   2.694  1.00  0.00           H  
HETATM   79  H49 UNL     1      -7.564  -0.253   1.439  1.00  0.00           H  
HETATM   80  H50 UNL     1      -6.617  -1.166   2.642  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4   28   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7    8   41
CONECT    7   42   43   44
CONECT    8    9   26   45
CONECT    9   10   46   47
CONECT   10   11   48   49
CONECT   11   12   26   50
CONECT   12   13   23   51
CONECT   13   14   52   53
CONECT   14   15   15   54
CONECT   15   16   21
CONECT   16   17   55   56
CONECT   17   18   19   57
CONECT   18   58
CONECT   19   20   59   60
CONECT   20   21   61   62
CONECT   21   22   23
CONECT   22   63   64   65
CONECT   23   24   66
CONECT   24   25   67   68
CONECT   25   26   69   70
CONECT   26   27
CONECT   27   71   72   73
CONECT   28   29   30   74
CONECT   29   75   76   77
CONECT   30   78   79   80
END

HMDB0000852
     RDKit          3D
beta-Sitosterol
 80 83  0  0  0  0  0  0  0  0999 V2000
   -6.6627    1.8491   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3580    1.9523    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218    1.1671    0.7913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9248    1.6484    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5683    1.0972    0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3407   -0.2931   -0.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5795   -0.4037   -1.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -0.8837    0.2466 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9685   -2.2933   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700   -2.4480   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668   -1.4481    0.0270 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5189   -1.0160   -0.4197 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4449   -2.2291   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855   -1.6616   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511   -0.4357   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5481   -0.0177   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2773    0.3309    0.2994 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5748    0.7359    0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5005    1.4630    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196    1.0167    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044    0.5474    0.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9926    1.6973   -0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -0.1665    0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1057    0.6910    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.7498    0.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332   -0.2272   -0.0940 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3904    0.3717   -1.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4283   -0.2456    1.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8867   -1.0858   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6331   -0.2439    2.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6061    1.2375   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9995    2.8718   -1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8732    1.5707   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1226    3.0276    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2383    1.6867    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    1.5998    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0708    1.7280   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    2.7893    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313    1.8290   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143    1.1075    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809   -0.9513    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -0.9810   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7713    0.6184   -2.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607   -0.9180   -2.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -0.9864    1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204   -2.5398   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -3.0545    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536   -3.4793   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528   -2.3241   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261   -1.7930    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5468   -0.4781   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -2.7282    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -2.8961   -1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4647   -2.3360   -1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0550   -0.7714   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188    0.8902   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -0.5169    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2208   -0.0344    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5163    2.3828    0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0407    1.6849    1.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2056    0.1582    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    1.8714    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1326    2.3030   -0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7675    1.2712   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9004    2.3071   -0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -0.9081    1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1151    0.4675    2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5426    1.7387    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068    0.6522    1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661    1.7735    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4285    0.9887   -1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045   -0.3325   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2602    1.0968   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6636   -0.7424    1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7288   -0.7063   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9740   -1.3852   -0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3480   -2.0804   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5902    0.6144    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5639   -0.2532    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6174   -1.1659    2.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  1
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  1
 12 51  1  6
 13 52  1  0
 13 53  1  0
 14 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  1
 18 58  1  0
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 22 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  1
 24 67  1  0
 24 68  1  0
 25 69  1  0
 25 70  1  0
 27 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 30 80  1  0
M  END

Synonyms

Value	Source
(-)-beta-Sitosterol	ChEBI
(24R)-Ethylcholest-5-en-3beta-ol	ChEBI
(24R)-Stigmast-5-en-3beta-ol	ChEBI
(3beta)-Stigmast-5-en-3-ol	ChEBI
22,23-Dihydrostigmasterol	ChEBI
24alpha-Ethylcholesterol	ChEBI
alpha-Dihydrofucosterol	ChEBI
Azuprostat	ChEBI
beta-Sitosterin	ChEBI
Cupreol	ChEBI
Nimbosterol	ChEBI
Triastonal	ChEBI
Sitosterol	Kegg
Harzol	Kegg
(-)-b-Sitosterol	Generator
(-)-Β-sitosterol	Generator
(24R)-Ethylcholest-5-en-3b-ol	Generator
(24R)-Ethylcholest-5-en-3β-ol	Generator
(24R)-Stigmast-5-en-3b-ol	Generator
(24R)-Stigmast-5-en-3β-ol	Generator
(3b)-Stigmast-5-en-3-ol	Generator
(3Β)-stigmast-5-en-3-ol	Generator
24a-Ethylcholesterol	Generator
24Α-ethylcholesterol	Generator
a-Dihydrofucosterol	Generator
Α-dihydrofucosterol	Generator
b-Sitosterin	Generator
Β-sitosterin	Generator
b-Sitosterol	Generator
Β-sitosterol	Generator
24-Ethylcholest-5-en-3 beta-ol	HMDB
24-Ethylcholesterol	HMDB
3beta-Sitosterol	HMDB
3beta-Stigmast-5-en-3-ol	HMDB
Clionasterol	HMDB
Sitosterol, (3beta)-isomer	HMDB
22,23-Dihydro-stigmasterol	HMDB
a-Phytosterol	HMDB
alpha-Phytosterol	HMDB
Angelicin	HMDB
beta-Phytosterol	HMDB
Cinchol	HMDB
D5-Stigmasten-3b-ol	HMDB
Delta5-Stigmasten-3b-ol	HMDB
Phytosterol	HMDB
Prostasal	HMDB
Quebrachol	HMDB
Rhamnol	HMDB
Sito-lande	HMDB
Sobatum	HMDB
Stigmast-5-en-3-ol	HMDB
Stigmast-5-en-3b-ol	HMDB
Stigmast-5-en-3beta-ol	HMDB
Stigmast-5-en-3β-ol	HMDB
delta5-Stigmasten-3beta-ol	HMDB
Δ5-stigmasten-3β-ol	HMDB
Α-phytosterol	HMDB
Rhammol	HMDB
Δ5-stigmasten-3beta-ol	HMDB
beta-Sitosterol	ChEBI

Molecular Formula

C₂₉H₅₀O

Average Mass

414.718

Monoisotopic Mass

414.38616623

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

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)CC[C@@H](CC)C(C)C

InChI Identifier

InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

KZJWDPNRJALLNS-VJSFXXLFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:27693 )
phytosterols (CHEBI:27693 )
stigmastane (C01753 )
Stigmasterols and C24-ethyl derivatives (C01753 )
Stigmasterols and C24-ethyl derivatives (LMST01040129 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.8e-05 g/L	ALOGPS
logP	7.27	ALOGPS
logP	7.84	ChemAxon
logS	-7.4	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	6	ChemAxon
Refractivity	129.77 m³·mol⁻¹	ChemAxon
Polarizability	54.21 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	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-054k-3912000000-22f633cd1bdd2ecca960	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0aor-9810000000-ab4d6cb3490b23c5cb70	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-5947700000-fe0573c7669e97c469f5	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-2931000000-0d63e91b728deb1446a4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9822000000-2be95863c114e7cd2597	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9601000000-edade780f6cfb8ddc7d1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-054k-3912000000-22f633cd1bdd2ecca960	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052v-1109000000-2eef6dd56a6c52421610	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-4103900000-a09c1c265657e57bd096	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	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0002900000-f2b81675160568c483c5	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-05nb-3930100000-897e65b10be8a412585c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a59-6900000000-b62b8d1bd807fc41256b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0aor-9810000000-fcbfd841778e213b3d3e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-03di-5947700000-4234b723ccdb0e25d290	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive	splash10-0002-2931000000-b2156fbd63c29312b076	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0a4l-9822000000-2be95863c114e7cd2597	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0019500000-b9eddfa8d56747167ada	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-5139100000-42d184a108f9e994dc01	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9076000000-54ef98673160128cbacd	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-158617c2e43f1a46b58a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0004900000-632250471791929b07e3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-2019000000-717c6229722cf73f3faa	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-eda302082c5114b2ab3a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0001900000-86165feb8e32cd8692ad	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0001900000-1fc08db7654e3c4918f9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4117900000-f005f19377309e9fb82d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06du-9146100000-d28aeb2182048e0912fa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9511000000-ff6bd6e1f8902e32555d	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9821000000-0f43ba6def9281d5c86d	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Fibroblasts
Intestine
Kidney
Liver
Prostate
Testis
Urine

Tissue Locations

Fibroblasts
Intestine
Kidney
Liver
Prostate
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193337	Delta(24)-sterol reductase	Unknown	Q15392	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Short bowel syndrome		Association	Human Blood	HMDB	15896428
Sitosterolemia	Increased	Association	Human Urine	HMDB	17613052

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Eukaryota/Fungi	Basidiomycota	9	Human feces
Eukaryota/Fungi	Blastocladiomycota	1
Eukaryota/Fungi	Ascomycota	8	Human feces; Human
Eukaryota/Fungi	Mucoromycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	14.1	10.6	uM	Adult (>18 years old)	Both	Short bowel syndrome	HMDB	15896428
Human Urine	Detected and Quantified	0.0021		umol/mmol creatinine	Adult (>18 years old)	Female	Sitosterolemia	HMDB	17613052
Human Urine	Detected and Quantified	0.00017	0.000095	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	17613052
Human Blood	Detected and Quantified	0.902	0.089	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	22.8	6.7	uM	Adult (>18 years old)	Both	Normal	HMDB	15896428
Human Blood	Detected and Quantified	5.53	0.021	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	8.222	4.340	uM	Adult (>18 years old)	Female	Normal	HMDB	11432711
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	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 Testis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Infant (0-1 year old)	NULL	Normal	HMDB	24628373
Human Feces	Detected but not Quantified				Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified				Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
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

External Links

HMDB ID

HMDB0000852

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Beta-Sitosterol

METLIN ID

169

PubChem Compound

222284

PDB ID

Not Available

ChEBI ID

27693

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bhattacharyya AK, Lopez LA: Absorbability of plant sterols and their distribution in rabbit tissues. Biochim Biophys Acta. 1979 Jul 27;574(1):146-53. doi: 10.1016/0005-2760(79)90093-6. [PubMed:573140 ]
Nikkila K, Hockerstedt K, Miettinen TA: Liver transplantation modifies serum cholestanol, cholesterol precursor and plant sterol levels. Clin Chim Acta. 1992 Jun 30;208(3):205-18. doi: 10.1016/0009-8981(92)90077-4. [PubMed:1499139 ]
Ling WH, Jones PJ: Dietary phytosterols: a review of metabolism, benefits and side effects. Life Sci. 1995;57(3):195-206. doi: 10.1016/0024-3205(95)00263-6. [PubMed:7596226 ]
Nguyen LB, Salen G, Shefer S, Bullock J, Chen T, Tint GS, Chowdhary IR, Lerner S: Deficient ileal 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in sitosterolemia: sitosterol is not a feedback inhibitor of intestinal cholesterol biosynthesis. Metabolism. 1994 Jul;43(7):855-9. doi: 10.1016/0026-0495(94)90266-6. [PubMed:8028508 ]
Clayton PT, Bowron A, Mills KA, Massoud A, Casteels M, Milla PJ: Phytosterolemia in children with parenteral nutrition-associated cholestatic liver disease. Gastroenterology. 1993 Dec;105(6):1806-13. doi: 10.1016/0016-5085(93)91079-w. [PubMed:8253356 ]
Sviridov DD, Safonova IG, Nano JL, Pavlov MY, Rampal P, Repin VS, Smirnov VN: New model to study cholesterol uptake in the human intestine in vitro. J Lipid Res. 1993 Feb;34(2):331-9. [PubMed:8429265 ]
Wilt TJ, MacDonald R, Ishani A: beta-sitosterol for the treatment of benign prostatic hyperplasia: a systematic review. BJU Int. 1999 Jun;83(9):976-83. doi: 10.1046/j.1464-410x.1999.00026.x. [PubMed:10368239 ]
Honda A, Salen G, Honda M, Batta AK, Tint GS, Xu G, Chen TS, Tanaka N, Shefer S: 3-Hydroxy-3-methylglutaryl-coenzyme A reductase activity is inhibited by cholesterol and up-regulated by sitosterol in sitosterolemic fibroblasts. J Lab Clin Med. 2000 Feb;135(2):174-9. doi: 10.1067/mlc.2000.104459. [PubMed:10695663 ]
Rajaratnam RA, Gylling H, Miettinen TA: Independent association of serum squalene and noncholesterol sterols with coronary artery disease in postmenopausal women. J Am Coll Cardiol. 2000 Apr;35(5):1185-91. doi: 10.1016/s0735-1097(00)00527-1. [PubMed:10758959 ]
Awad AB, Downie A, Fink CS, Kim U: Dietary phytosterol inhibits the growth and metastasis of MDA-MB-231 human breast cancer cells grown in SCID mice. Anticancer Res. 2000 Mar-Apr;20(2A):821-4. [PubMed:10810360 ]
Stalenhoef AF, Hectors M, Demacker PN: Effect of plant sterol-enriched margarine on plasma lipids and sterols in subjects heterozygous for phytosterolaemia. J Intern Med. 2001 Feb;249(2):163-6. doi: 10.1046/j.1365-2796.2001.00788.x. [PubMed:11240845 ]
Li JH, Awad AB, Fink CS, Wu YW, Trevisan M, Muti P: Measurement variability of plasma beta-sitosterol and campesterol, two new biomarkers for cancer prevention. Eur J Cancer Prev. 2001 Jun;10(3):245-9. doi: 10.1097/00008469-200106000-00007. [PubMed:11432711 ]
Awad AB, Roy R, Fink CS: Beta-sitosterol, a plant sterol, induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells. Oncol Rep. 2003 Mar-Apr;10(2):497-500. [PubMed:12579296 ]
Maguire L, Konoplyannikov M, Ford A, Maguire AR, O'Brien NM: Comparison of the cytotoxic effects of beta-sitosterol oxides and a cholesterol oxide, 7beta-hydroxycholesterol, in cultured mammalian cells. Br J Nutr. 2003 Oct;90(4):767-75. doi: 10.1079/bjn2003956. [PubMed:13129445 ]
Kim BH, Lee YS, Kang KS: The mechanism of retinol-induced irritation and its application to anti-irritant development. Toxicol Lett. 2003 Dec 15;146(1):65-73. doi: 10.1016/j.toxlet.2003.09.001. [PubMed:14615068 ]
Muti P, Awad AB, Schunemann H, Fink CS, Hovey K, Freudenheim JL, Wu YW, Bellati C, Pala V, Berrino F: A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. J Nutr. 2003 Dec;133(12):4252-5. doi: 10.1093/jn/133.12.4252. [PubMed:14652381 ]
Madersbacher S, Schatzl G, Brossner C, Dreikorn K: [Phytotherapy for BPS. Which products can still be prescribed?]. Urologe A. 2005 May;44(5):513-20. doi: 10.1007/s00120-005-0778-8. [PubMed:15726313 ]
Miwa K, Inazu A, Kobayashi J, Higashikata T, Nohara A, Kawashiri M, Katsuda S, Takata M, Koizumi J, Mabuchi H: ATP-binding cassette transporter G8 M429V polymorphism as a novel genetic marker of higher cholesterol absorption in hypercholesterolaemic Japanese subjects. Clin Sci (Lond). 2005 Aug;109(2):183-8. doi: 10.1042/CS20050030. [PubMed:15816807 ]
Barthomeuf C, Grassi J, Demeule M, Fournier C, Boivin D, Beliveau R: Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin. Cancer Chemother Pharmacol. 2005 Aug;56(2):173-81. doi: 10.1007/s00280-004-0914-y. Epub 2005 Apr 12. [PubMed:15824923 ]
Fernandez ML, Vega-Lopez S: Efficacy and safety of sitosterol in the management of blood cholesterol levels. Cardiovasc Drug Rev. 2005 Spring;23(1):57-70. doi: 10.1111/j.1527-3466.2005.tb00157.x. [PubMed:15867948 ]
Kabouche A, Boutaghane N, Kabouche Z, Seguin E, Tillequin F, Benlabed K: Components and antibacterial activity of the roots of Salvia jaminiana. Fitoterapia. 2005 Jul;76(5):450-2. doi: 10.1016/j.fitote.2005.03.011. [PubMed:15893885 ]
Miettinen TA, Railo M, Lepantalo M, Gylling H: Plant sterols in serum and in atherosclerotic plaques of patients undergoing carotid endarterectomy. J Am Coll Cardiol. 2005 Jun 7;45(11):1794-801. doi: 10.1016/j.jacc.2005.02.063. [PubMed:15936608 ]
Calpe-Berdiel L, Escola-Gil JC, Ribas V, Navarro-Sastre A, Garces-Garces J, Blanco-Vaca F: Changes in intestinal and liver global gene expression in response to a phytosterol-enriched diet. Atherosclerosis. 2005 Jul;181(1):75-85. doi: 10.1016/j.atherosclerosis.2004.11.025. Epub 2005 Feb 12. [PubMed:15939057 ]
Gylling H, Miettinen TA: The effect of plant stanol- and sterol-enriched foods on lipid metabolism, serum lipids and coronary heart disease. Ann Clin Biochem. 2005 Jul;42(Pt 4):254-63. doi: 10.1258/0004563054255605. [PubMed:15989725 ]
Siirtola A, Ketomaki A, Miettinen TA, Gylling H, Lehtimaki T, Holmberg C, Salo MK, Antikainen M: Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. Transplantation. 2006 Feb 15;81(3):327-34. doi: 10.1097/01.tp.0000189173.46727.18. [PubMed:16477216 ]

Showing metabocard for beta-Sitosterol (MMDBc0052894)

MOL for #<Metabolite:0x00007fd108d00f08>

3D MOL for #<Metabolite:0x00007fd108d00f08>

3D SDF for #<Metabolite:0x00007fd108d00f08>

3D-SDF for #<Metabolite:0x00007fd108d00f08>

PDB for #<Metabolite:0x00007fd108d00f08>

3D PDB for #<Metabolite:0x00007fd108d00f08>

SMILES for #<Metabolite:0x00007fd108d00f08>

INCHI for #<Metabolite:0x00007fd108d00f08>

Structure for #<Metabolite:0x00007fd108d00f08>

3D Structure for #<Metabolite:0x00007fd108d00f08>