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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (8) Show 9 proteins XML

enzymes (1)transporters (8) Show 9 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000308

Secondary Accession Numbers

HMDB00308

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>
HMDB0000308

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₂₄H₃₈O₃

Average Molecular Weight

374.5567

Monoisotopic Molecular Weight

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

5255-17-4

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000308)
Saliva (HMDB: HMDB0000308)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27543620)

Cellular substructure

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000308)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000308)

Source

Endogenous

Endogenous (HMDB: HMDB0000308)

Animal

Animal (HMDB: HMDB0000308)

Exogenous

Food

Food (HMDB: HMDB0000308)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000308)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000308)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000308)

Lipid metabolism pathway (HMDB: HMDB0000308)

Cellular process

Cell signaling (HMDB: HMDB0000308)

Biochemical process

Lipid transport (HMDB: HMDB0000308)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000308)

Molecular messenger

Signaling molecule (HMDB: HMDB0000308)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000308)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.045	31661259
DarkChem	[M-H]-	184.774	31661259
AllCCS	[M+H]+	197.822	32859911
AllCCS	[M-H]-	197.41	32859911
DeepCCS	[M-2H]-	229.8	30932474
DeepCCS	[M+Na]+	205.214	30932474
AllCCS	[M+H]+	197.8	32859911
AllCCS	[M+H-H2O]+	195.5	32859911
AllCCS	[M+NH4]+	200.0	32859911
AllCCS	[M+Na]+	200.6	32859911
AllCCS	[M-H]-	197.4	32859911
AllCCS	[M+Na-2H]-	198.5	32859911
AllCCS	[M+HCOO]-	199.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3b-Hydroxy-5-cholenoic acid	[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	3567.6	Standard polar	33892256
3b-Hydroxy-5-cholenoic acid	[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	3151.7	Standard non polar	33892256
3b-Hydroxy-5-cholenoic acid	[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	3254.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3b-Hydroxy-5-cholenoic acid,1TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3203.3	Semi standard non polar	33892256
3b-Hydroxy-5-cholenoic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3311.6	Semi standard non polar	33892256
3b-Hydroxy-5-cholenoic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3248.2	Semi standard non polar	33892256
3b-Hydroxy-5-cholenoic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3488.0	Semi standard non polar	33892256
3b-Hydroxy-5-cholenoic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3537.2	Semi standard non polar	33892256
3b-Hydroxy-5-cholenoic acid,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3770.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ktb-0119000000-d9c374e9f5f5293a5dca	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0udi-2115890000-77f8ec28775146b3a80a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b-Hydroxy-5-cholenoic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4j-9538000000-967e828abd3f3d7ea705	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00kf-9800000000-fd3b7c3599b83e132518	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0w29-1695000000-3a7e6bdffc7807847034	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 10V, Positive-QTOF	splash10-0a4i-0009000000-d81080951979776b8851	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 20V, Positive-QTOF	splash10-0bvr-0029000000-57d452e5f3215053dec5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 40V, Positive-QTOF	splash10-052b-2296000000-bc9371e40f0a8181ee48	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 10V, Negative-QTOF	splash10-00di-0009000000-5f1cbb9d5b0d94fca8ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 20V, Negative-QTOF	splash10-0ab9-0009000000-81084972d3f11745deaa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-cc93a4f9f513c8d5c003	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 10V, Negative-QTOF	splash10-00di-0009000000-666fef074d788c106dcb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 20V, Negative-QTOF	splash10-05fr-0009000000-7995f4531885f9d2edf6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 40V, Negative-QTOF	splash10-0a4i-4059000000-4a851016b0c31ca828ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 10V, Positive-QTOF	splash10-056r-0009000000-589eec7541e9d9499e9a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 20V, Positive-QTOF	splash10-0a4s-3298000000-26204184430e4b9552c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-5-cholenoic acid 40V, Positive-QTOF	splash10-0a4i-3941000000-109ac8dcc89c0c4c8858	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	0.015 (0.004-0.030) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	493-15753 umol/mmol creatinine	Infant (0-1 year old)	Both	Bile Acid Synthesis Defect, Congenital, 1	25931455	details
Urine	Detected and Quantified	441 umol/mmol creatinine	Children (1-13 years old)	Female	Bile Acid Synthesis Defect, Congenital, 1	25931455	details

Associated Disorders and Diseases

Disease References

Bile Acid Synthesis Defect, Congenital, 1

Zhang W, Jha P, Wolfe B, Gioiello A, Pellicciari R, Wang J, Heubi J, Setchell KD: Tandem mass spectrometric determination of atypical 3beta-hydroxy-Delta5-bile acids in patients with 3beta-hydroxy-Delta5-C27-steroid oxidoreductase deficiency: application to diagnosis and monitoring of bile acid therapeutic response. Clin Chem. 2015 Jul;61(7):955-63. doi: 10.1373/clinchem.2015.238238. Epub 2015 Apr 30. [PubMed:25931455 ]

Associated OMIM IDs

607765 (Bile Acid Synthesis Defect, Congenital, 1)

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Burton, Gerardo; Gros, Eduardo G. Synthesis of 3b-hydroxy-5-cholenic acid from 3b-hydroxy-5-pregnen-20-one aimed at the preparation of labeled steroid compounds. Journal of Steroid Biochemistry (1977), 8(1), 69-72.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:12829005 ]
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. [PubMed:10203155 ]
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. [PubMed:3794931 ]
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. [PubMed:11316487 ]
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. Epub 2005 Jul 21. [PubMed:16037564 ]
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. [PubMed:12576301 ]
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 ]
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 ]
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. [PubMed:3987031 ]
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. [PubMed:1641875 ]

Enzymes

Enzyme Details

1. Gastrotropin

General function:: Involved in binding
Specific function:: Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:: FABP6
Uniprot ID:: P51161
Molecular weight:: 14371.2

References

Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B3

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:: SLCO1B3
Uniprot ID:: Q9NPD5
Molecular weight:: 77402.2

Enzyme Details

2. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]

Enzyme Details

3. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

Enzyme Details

4. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

Enzyme Details

5. Ileal sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:: SLC10A2
Uniprot ID:: Q12908
Molecular weight:: 37697.4

References

Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]

Enzyme Details

6. Sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:: SLC10A1
Uniprot ID:: Q14973
Molecular weight:: 38118.64

Enzyme Details

7. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

Enzyme Details

8. Solute carrier organic anion transporter family member 4A1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:: SLCO4A1
Uniprot ID:: Q96BD0
Molecular weight:: 77192.5

Showing metabocard for 3b-Hydroxy-5-cholenoic acid (HMDB0000308)

MOL for HMDB0000308 (3b-Hydroxy-5-cholenoic acid)

3D MOL for HMDB0000308 (3b-Hydroxy-5-cholenoic acid)

3D SDF for HMDB0000308 (3b-Hydroxy-5-cholenoic acid)

3D-SDF for HMDB0000308 (3b-Hydroxy-5-cholenoic acid)

PDB for HMDB0000308 (3b-Hydroxy-5-cholenoic acid)

3D PDB for HMDB0000308 (3b-Hydroxy-5-cholenoic acid)

SMILES for HMDB0000308 (3b-Hydroxy-5-cholenoic acid)

INCHI for HMDB0000308 (3b-Hydroxy-5-cholenoic acid)

Structure for HMDB0000308 (3b-Hydroxy-5-cholenoic acid)

3D Structure for HMDB0000308 (3b-Hydroxy-5-cholenoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

References

References