MiMeDB: Showing metabocard for 3b-Hydroxy-5-cholenoic acid (MMDBc0000339)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:35:41 UTC

Update Date

2024-04-30 19:31:51 UTC

Metabolite ID

MMDBc0000339

Metabolite Identification

Common Name

3b-Hydroxy-5-cholenoic acid

Description

3b-Hydroxy-5-cholenoic acid, also known as 3b-hydroxy-chol-5-en-24-oate or cholenate, belongs to the class of organic compounds known as monohydroxy bile acids. These are bile acids bearing a hydroxyl group. Bile acids facilitate fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH, and consequently require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). When present in sufficiently high levels, bile acids can act as hepatotoxins and metabotoxisn. A hepatotoxin causes damage to the liver or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (PMID: 1641875 ). The liver toxicity of bile acids appears to be due to their ability to peroxidate lipids and to lyse liver cells. Chronically high levels of cholic acid are associated with familial hypercholanemia. In hypercholanemia, bile acids are elevated in the blood. This disease causes liver damage, extensive itching, poor fat absorption, and can lead to rickets due to lack of calcium in bones. The deficiency of normal bile acids in the intestines results in a deficiency of vitamin K, which also adversely affects clotting of the blood.

Structure

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

3b-Hydroxy-5-cholenoic acid.mol
  Mrv1652305261923592D          

 30 33  0  0  0  0            999 V2000
   -2.4539   -2.5401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4539   -1.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -1.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -2.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -2.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -2.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -2.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -1.7151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1184   -1.3026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9030   -1.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880   -0.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030   -0.2227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1580    0.5619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5746    1.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    1.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    2.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    0.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.4776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1184    0.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -0.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -1.3026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0250   -1.7151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0250   -0.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986    2.9526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1684    1.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -2.9526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -2.1276    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.8901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -2.1276    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  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
 12 11  1  1  0  0  0
 12 13  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
 13 17  1  1  0  0  0
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
  1 27  1  1  0  0  0
 22 28  1  6  0  0  0
  8 29  1  1  0  0  0
  9 30  1  6  0  0  0
M  END

HMDB0000308
     RDKit          3D
3b-Hydroxy-5-cholenoic acid
 65 68  0  0  0  0  0  0  0  0999 V2000
    4.8251    0.9108    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -0.0442    0.2545 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0662   -1.4186   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1974   -2.0064    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4967   -1.3753    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2076   -1.6098   -0.4288 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0447   -0.5262    1.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802    0.5198   -0.3474 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5133    0.7794   -1.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0284    0.9902   -2.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3403    0.9411   -0.8668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1080    0.7388   -0.8423 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7579    2.0714   -1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1373    2.1322   -0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603    1.1790    0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1672    1.4419    0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8270    0.1610    0.8015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3044   -0.5417   -0.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0566   -0.6958    1.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5942   -0.7505    1.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476   -0.0808    0.3437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1590   -1.1067   -0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926    0.2983    0.5050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7751   -0.7580    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630   -0.2714    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1729   -0.1586   -0.1750 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9778   -1.3970   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6177    0.5414   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1938    1.3410    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3908    1.8082   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -0.0205    1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3912   -1.5079   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -2.1692    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8752   -1.9109    1.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.1241    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4006    0.4008    1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3562    1.5508    0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9604   -0.0174   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0728    1.7152   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9020    2.0261   -2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    0.2408   -2.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6048    1.8720   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4632    0.0518   -1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850    2.8636   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    2.3371   -2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6790    3.0761   -0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2318    2.1376    1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7370    1.9114   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7835    0.4575    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4709    0.1800   -1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5114   -1.7284    1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2817   -0.3559    2.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2650   -1.8194    1.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0535   -0.3250    2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952   -0.5969   -1.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9270   -1.8935   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137   -1.6802   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745    1.2012    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084   -0.8797    2.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8735   -1.7249    0.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -0.9254    1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391    0.7320    1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.5435   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8237   -2.3162   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -1.3290   -1.6098 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  2  0
  5  7  1  0
  2  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
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  1
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  8 37  1  1
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  1
 12 43  1  6
 13 44  1  0
 13 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  1
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 22 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  1
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
M  END

3b-Hydroxy-5-cholenoic acid.mol
  Mrv1652305261923592D          

 30 33  0  0  0  0            999 V2000
   -2.4539   -2.5401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4539   -1.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -1.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -2.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -2.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -2.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -2.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -1.7151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1184   -1.3026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9030   -1.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880   -0.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030   -0.2227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1580    0.5619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5746    1.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    1.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    2.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    0.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.4776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1184    0.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -0.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -1.3026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0250   -1.7151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0250   -0.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986    2.9526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1684    1.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -2.9526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -2.1276    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.8901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -2.1276    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  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
 12 11  1  1  0  0  0
 12 13  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
 13 17  1  1  0  0  0
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
  1 27  1  1  0  0  0
 22 28  1  6  0  0  0
  8 29  1  1  0  0  0
  9 30  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000339

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5,15,17-21,25H,4,6-14H2,1-3H3,(H,26,27)/t15-,17+,18+,19-,20+,21+,23+,24-/m1/s1

> <INCHI_KEY>
HIAJCGFYHIANNA-QIZZZRFXSA-N

> <FORMULA>
C24H38O3

> <MOLECULAR_WEIGHT>
374.5567

> <EXACT_MASS>
374.282095082

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.29105829785729

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
4.616490839333335

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.20428950550382

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.831011168990334

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972440270538904

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
108.53129999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000308
     RDKit          3D
3b-Hydroxy-5-cholenoic acid
 65 68  0  0  0  0  0  0  0  0999 V2000
    4.8251    0.9108    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -0.0442    0.2545 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0662   -1.4186   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1974   -2.0064    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4967   -1.3753    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2076   -1.6098   -0.4288 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0447   -0.5262    1.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802    0.5198   -0.3474 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5133    0.7794   -1.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0284    0.9902   -2.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3403    0.9411   -0.8668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1080    0.7388   -0.8423 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7579    2.0714   -1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1373    2.1322   -0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603    1.1790    0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1672    1.4419    0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8270    0.1610    0.8015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3044   -0.5417   -0.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0566   -0.6958    1.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5942   -0.7505    1.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476   -0.0808    0.3437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1590   -1.1067   -0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926    0.2983    0.5050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7751   -0.7580    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630   -0.2714    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1729   -0.1586   -0.1750 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9778   -1.3970   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6177    0.5414   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1938    1.3410    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3908    1.8082   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -0.0205    1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3912   -1.5079   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -2.1692    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8752   -1.9109    1.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.1241    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4006    0.4008    1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3562    1.5508    0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9604   -0.0174   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0728    1.7152   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9020    2.0261   -2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    0.2408   -2.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6048    1.8720   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4632    0.0518   -1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850    2.8636   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    2.3371   -2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6790    3.0761   -0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2318    2.1376    1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7370    1.9114   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7835    0.4575    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4709    0.1800   -1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5114   -1.7284    1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2817   -0.3559    2.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2650   -1.8194    1.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0535   -0.3250    2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952   -0.5969   -1.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9270   -1.8935   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137   -1.6802   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745    1.2012    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084   -0.8797    2.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8735   -1.7249    0.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -0.9254    1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391    0.7320    1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.5435   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8237   -2.3162   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -1.3290   -1.6098 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  2  0
  5  7  1  0
  2  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
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  1
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  8 37  1  1
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  1
 12 43  1  6
 13 44  1  0
 13 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  1
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 22 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  1
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3b-Hydroxy-5-cholenoic acid.mol                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.581  -4.742   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.581  -3.202   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.247  -2.432   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.247  -5.512   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.913  -4.742   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.580  -5.512   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.754  -4.742   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.754  -3.202   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.088  -2.432   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.552  -2.908   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.458  -1.662   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.552  -0.416   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.028   1.049   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.939   2.138   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.338   3.625   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.825   4.024   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.535   1.369   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.088  -0.892   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.088   0.648   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.754  -0.122   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.580  -0.892   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.580  -2.432   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.913  -3.202   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.913  -1.662   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.224   5.512   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.914   2.935   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.914  -5.512   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0      -0.580  -3.972   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.754  -1.662   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.088  -3.972   0.000  0.00  0.00           H+0
CONECT    1    2    4   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2   23                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   22   29                                             
CONECT    9    8   10   18   30                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   25   26                                                  
CONECT   17   13                                                            
CONECT   18   12    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    8   23   28                                             
CONECT   23   22    3    5   24                                             
CONECT   24   23                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27    1                                                            
CONECT   28   22                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0000308
HETATM    1  C1  UNL     1       4.825   0.911   0.019  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.690  -0.044   0.254  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.066  -1.419  -0.066  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.197  -2.006   0.720  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.497  -1.375   0.610  1.00  0.00           C  
HETATM    6  O1  UNL     1       7.208  -1.610  -0.429  1.00  0.00           O  
HETATM    7  O2  UNL     1       7.045  -0.526   1.551  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.480   0.520  -0.347  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.513   0.779  -1.837  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.028   0.990  -2.186  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.340   0.941  -0.867  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.108   0.739  -0.842  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.758   2.071  -1.143  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.137   2.132  -0.663  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.760   1.179   0.015  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.167   1.442   0.411  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.827   0.161   0.801  1.00  0.00           C  
HETATM   18  O3  UNL     1      -6.304  -0.542  -0.331  1.00  0.00           O  
HETATM   19  C16 UNL     1      -5.057  -0.696   1.733  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.594  -0.751   1.569  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.048  -0.081   0.344  1.00  0.00           C  
HETATM   22  C19 UNL     1      -3.159  -1.107  -0.792  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.593   0.298   0.505  1.00  0.00           C  
HETATM   24  C21 UNL     1      -0.775  -0.758   1.152  1.00  0.00           C  
HETATM   25  C22 UNL     1       0.663  -0.271   1.212  1.00  0.00           C  
HETATM   26  C23 UNL     1       1.173  -0.159  -0.175  1.00  0.00           C  
HETATM   27  C24 UNL     1       0.978  -1.397  -0.998  1.00  0.00           C  
HETATM   28  H1  UNL     1       5.618   0.541  -0.648  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.194   1.341   0.978  1.00  0.00           H  
HETATM   30  H3  UNL     1       4.391   1.808  -0.529  1.00  0.00           H  
HETATM   31  H4  UNL     1       3.510  -0.020   1.385  1.00  0.00           H  
HETATM   32  H5  UNL     1       4.391  -1.508  -1.153  1.00  0.00           H  
HETATM   33  H6  UNL     1       3.250  -2.169   0.001  1.00  0.00           H  
HETATM   34  H7  UNL     1       4.875  -1.911   1.809  1.00  0.00           H  
HETATM   35  H8  UNL     1       5.237  -3.124   0.580  1.00  0.00           H  
HETATM   36  H9  UNL     1       7.401   0.401   1.287  1.00  0.00           H  
HETATM   37  H10 UNL     1       2.356   1.551   0.107  1.00  0.00           H  
HETATM   38  H11 UNL     1       2.960  -0.017  -2.421  1.00  0.00           H  
HETATM   39  H12 UNL     1       3.073   1.715  -2.073  1.00  0.00           H  
HETATM   40  H13 UNL     1       0.902   2.026  -2.595  1.00  0.00           H  
HETATM   41  H14 UNL     1       0.684   0.241  -2.908  1.00  0.00           H  
HETATM   42  H15 UNL     1       0.605   1.872  -0.304  1.00  0.00           H  
HETATM   43  H16 UNL     1      -1.463   0.052  -1.664  1.00  0.00           H  
HETATM   44  H17 UNL     1      -1.185   2.864  -0.578  1.00  0.00           H  
HETATM   45  H18 UNL     1      -1.663   2.337  -2.223  1.00  0.00           H  
HETATM   46  H19 UNL     1      -3.679   3.076  -0.906  1.00  0.00           H  
HETATM   47  H20 UNL     1      -5.232   2.138   1.291  1.00  0.00           H  
HETATM   48  H21 UNL     1      -5.737   1.911  -0.404  1.00  0.00           H  
HETATM   49  H22 UNL     1      -6.783   0.457   1.331  1.00  0.00           H  
HETATM   50  H23 UNL     1      -6.471   0.180  -1.008  1.00  0.00           H  
HETATM   51  H24 UNL     1      -5.511  -1.728   1.693  1.00  0.00           H  
HETATM   52  H25 UNL     1      -5.282  -0.356   2.786  1.00  0.00           H  
HETATM   53  H26 UNL     1      -3.265  -1.819   1.528  1.00  0.00           H  
HETATM   54  H27 UNL     1      -3.053  -0.325   2.456  1.00  0.00           H  
HETATM   55  H28 UNL     1      -3.395  -0.597  -1.738  1.00  0.00           H  
HETATM   56  H29 UNL     1      -3.927  -1.893  -0.539  1.00  0.00           H  
HETATM   57  H30 UNL     1      -2.214  -1.680  -0.892  1.00  0.00           H  
HETATM   58  H31 UNL     1      -1.575   1.201   1.172  1.00  0.00           H  
HETATM   59  H32 UNL     1      -1.108  -0.880   2.192  1.00  0.00           H  
HETATM   60  H33 UNL     1      -0.874  -1.725   0.646  1.00  0.00           H  
HETATM   61  H34 UNL     1       1.275  -0.925   1.870  1.00  0.00           H  
HETATM   62  H35 UNL     1       0.639   0.732   1.684  1.00  0.00           H  
HETATM   63  H36 UNL     1       1.778  -1.543  -1.774  1.00  0.00           H  
HETATM   64  H37 UNL     1       0.824  -2.316  -0.383  1.00  0.00           H  
HETATM   65  H38 UNL     1       0.039  -1.329  -1.610  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    8   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6    6    7
CONECT    7   36
CONECT    8    9   26   37
CONECT    9   10   38   39
CONECT   10   11   40   41
CONECT   11   12   26   42
CONECT   12   13   23   43
CONECT   13   14   44   45
CONECT   14   15   15   46
CONECT   15   16   21
CONECT   16   17   47   48
CONECT   17   18   19   49
CONECT   18   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   23
CONECT   22   55   56   57
CONECT   23   24   58
CONECT   24   25   59   60
CONECT   25   26   61   62
CONECT   26   27
CONECT   27   63   64   65
END

HMDB0000308
     RDKit          3D
3b-Hydroxy-5-cholenoic acid
 65 68  0  0  0  0  0  0  0  0999 V2000
    4.8251    0.9108    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -0.0442    0.2545 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0662   -1.4186   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1974   -2.0064    0.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4967   -1.3753    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2076   -1.6098   -0.4288 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0447   -0.5262    1.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802    0.5198   -0.3474 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5133    0.7794   -1.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0284    0.9902   -2.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3403    0.9411   -0.8668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1080    0.7388   -0.8423 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7579    2.0714   -1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1373    2.1322   -0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603    1.1790    0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1672    1.4419    0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8270    0.1610    0.8015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3044   -0.5417   -0.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0566   -0.6958    1.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5942   -0.7505    1.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476   -0.0808    0.3437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1590   -1.1067   -0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926    0.2983    0.5050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7751   -0.7580    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630   -0.2714    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1729   -0.1586   -0.1750 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9778   -1.3970   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6177    0.5414   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1938    1.3410    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3908    1.8082   -0.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -0.0205    1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3912   -1.5079   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -2.1692    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8752   -1.9109    1.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.1241    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4006    0.4008    1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3562    1.5508    0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9604   -0.0174   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0728    1.7152   -2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9020    2.0261   -2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    0.2408   -2.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6048    1.8720   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4632    0.0518   -1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850    2.8636   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    2.3371   -2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6790    3.0761   -0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2318    2.1376    1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7370    1.9114   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7835    0.4575    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4709    0.1800   -1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5114   -1.7284    1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2817   -0.3559    2.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2650   -1.8194    1.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0535   -0.3250    2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952   -0.5969   -1.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9270   -1.8935   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2137   -1.6802   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745    1.2012    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084   -0.8797    2.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8735   -1.7249    0.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -0.9254    1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391    0.7320    1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -1.5435   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8237   -2.3162   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386   -1.3290   -1.6098 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  2  0
  5  7  1  0
  2  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
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  1
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  8 37  1  1
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  1
 12 43  1  6
 13 44  1  0
 13 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  1
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 22 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  1
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 27 63  1  0
 27 64  1  0
 27 65  1  0
M  END

Synonyms

Value	Source
3b-Hydroxy-5-cholenoate	Generator
3b-Hydroxy-chol-5-en-24-Oate	HMDB
3b-Hydroxy-chol-5-en-24-Oic acid	HMDB
3b-Hydroxychol-5-en-24-ate	HMDB
3b-Hydroxychol-5-en-24-ic acid	HMDB
3b-Hydroxychol-5-en-24-Oate	HMDB
3b-Hydroxychol-5-en-24-Oic acid	HMDB
3b-Hydroxychol-5-enoate	HMDB
3b-Hydroxychol-5-enoic acid	HMDB
3b-Hydroxycholenoate	HMDB
3b-Hydroxycholenoic acid	HMDB
3beta-Hydroxy-5-cholenic acid	HMDB
3beta-Hydroxy-5-cholenoate	HMDB
3beta-Hydroxy-5-cholenoic acid	HMDB
3beta-Hydroxy-chol-5-en-24-Oate	HMDB
3beta-Hydroxy-chol-5-en-24-Oic acid	HMDB
3beta-Hydroxy-delta5-cholenic acid	HMDB, MeSH
3beta-Hydroxychol-5-en-24-Oate	HMDB
3beta-Hydroxychol-5-en-24-Oic acid	HMDB
Cholenate	HMDB
Cholenic acid	HMDB
D5-Cholenate	HMDB
D5-Cholenic acid	HMDB
3 beta-Hydroxy-5-cholenic acid	MeSH, HMDB
3 beta-Hydroxy-delta 5-cholenic acid, sodium salt	MeSH, HMDB
3 beta-Hydroxy-delta 5-cholenic acid	MeSH, HMDB
3 beta-Hydroxy-5-cholenoic acid	MeSH, HMDB
(4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]pentanoate	Generator, HMDB

Molecular Formula

C₂₄H₃₈O₃

Average Mass

374.5567

Monoisotopic Mass

374.282095082

IUPAC Name

(4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C24H38O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5,15,17-21,25H,4,6-14H2,1-3H3,(H,26,27)/t15-,17+,18+,19-,20+,21+,23+,24-/m1/s1

InChI Key

HIAJCGFYHIANNA-QIZZZRFXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
3-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010201 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0035 g/L	ALOGPS
logP	4.54	ALOGPS
logP	4.62	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.53 m³·mol⁻¹	ChemAxon
Polarizability	45.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ktb-0119000000-d9c374e9f5f5293a5dca	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0udi-2115890000-77f8ec28775146b3a80a	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 (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4j-9538000000-967e828abd3f3d7ea705	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kf-9800000000-fd3b7c3599b83e132518	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0w29-1695000000-3a7e6bdffc7807847034	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0009000000-d81080951979776b8851	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bvr-0029000000-57d452e5f3215053dec5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052b-2296000000-bc9371e40f0a8181ee48	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-5f1cbb9d5b0d94fca8ae	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-0009000000-81084972d3f11745deaa	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-cc93a4f9f513c8d5c003	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-666fef074d788c106dcb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-0009000000-7995f4531885f9d2edf6	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-4059000000-4a851016b0c31ca828ca	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0009000000-589eec7541e9d9499e9a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-3298000000-26204184430e4b9552c8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3941000000-109ac8dcc89c0c4c8858	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192108	Solute carrier organic anion transporter family member 1B3	Transporter	Q9NPD5	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0193395	Canalicular multispecific organic anion transporter 2	Transporter	O15438	Homo sapiens
MMDBp0193400	Bile salt export pump	Transporter	O95342	Homo sapiens
MMDBp0193547	Ileal sodium/bile acid cotransporter	Transporter	Q12908	Homo sapiens
MMDBp0193577	Sodium/bile acid cotransporter	Transporter	Q14973	Homo sapiens
MMDBp0193639	Solute carrier organic anion transporter family member 1A2	Transporter	P46721	Homo sapiens
MMDBp0193865	Solute carrier organic anion transporter family member 4A1	Transporter	Q96BD0	Homo sapiens
MMDBp0195864	Gastrotropin	Unknown	P51161	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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	441			umol/mmol creatinine	Children (1-13 years old)	Female	Bile Acid Synthesis Defect, Congenital, 1	HMDB	25931455
Human Urine	Detected and Quantified		493	15753	umol/mmol creatinine	Infant (0-1 year old)	Both	Bile Acid Synthesis Defect, Congenital, 1	HMDB	25931455
Human Urine	Detected and Quantified	0.015	0.004	0.030	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
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	29808030
Human Blood	Detected but not Quantified								HMDB

External Links

HMDB ID

HMDB0000308

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021935

KNApSAcK ID

C00052229

Chemspider ID

83950

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5297

PubChem Compound

92997

PDB ID

Not Available

ChEBI ID

384794

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Delzenne NM, Calderon PB, Taper HS, Roberfroid MB: Comparative hepatotoxicity of cholic acid, deoxycholic acid and lithocholic acid in the rat: in vivo and in vitro studies. Toxicol Lett. 1992 Jul;61(2-3):291-304. doi: 10.1016/0378-4274(92)90156-e. [PubMed:1641875 ]
Vanderpas JB, Koopman BJ, Cadranel S, Vandenbergen C, Rickaert F, Quenon M, Wolthers BG, Brauherz G, Vertongen F, Tondeur M: Malabsorption of liposoluble vitamins in a child with bile acid deficiency. J Pediatr Gastroenterol Nutr. 1987 Jan-Feb;6(1):33-41. doi: 10.1097/00005176-198701000-00007. [PubMed:3794931 ]
Hernanz A, Codoceo R, Jara P, Diaz C: Unusual serum bile acid pattern in children with the syndrome of hepatic ductular hypoplasia. Clin Chim Acta. 1985 Feb 15;145(3):289-96. doi: 10.1016/0009-8981(85)90036-1. [PubMed:3987031 ]
Norman A, Strandvik B: Formation and metabolism of bile acids in extrahepatic biliary atresia. J Lab Clin Med. 1971 Aug;78(2):181-93. [PubMed:5567561 ]
Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. doi: 10.1203/00006450-199904010-00022. [PubMed:10203155 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. doi: 10.1242/jeb.204.10.1673. [PubMed:11316487 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. doi: 10.1152/ajpgi.00417.2002. [PubMed:12576301 ]
Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. doi: 10.1016/s1570-0232(03)00277-0. [PubMed:12829005 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. doi: 10.1161/01.ATV.0000178994.21828.a7. Epub 2005 Jul 21. [PubMed:16037564 ]

Showing metabocard for 3b-Hydroxy-5-cholenoic acid (MMDBc0000339)

MOL for #<Metabolite:0x00007fdb704afd78>

3D MOL for #<Metabolite:0x00007fdb704afd78>

3D SDF for #<Metabolite:0x00007fdb704afd78>

3D-SDF for #<Metabolite:0x00007fdb704afd78>

PDB for #<Metabolite:0x00007fdb704afd78>

3D PDB for #<Metabolite:0x00007fdb704afd78>

SMILES for #<Metabolite:0x00007fdb704afd78>

INCHI for #<Metabolite:0x00007fdb704afd78>

Structure for #<Metabolite:0x00007fdb704afd78>

3D Structure for #<Metabolite:0x00007fdb704afd78>