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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

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:02 UTC

HMDB ID

HMDB0000447

Secondary Accession Numbers

HMDB00447

Metabolite Identification

Common Name

7a,12a-Dihydroxy-3-oxo-4-cholenoic acid

Description

7a,12a-Dihydroxy-3-oxo-4-cholenoic acid, also known as 7alpha,12alpha-dihydroxy-3-oxochol-4-enoate, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Based on a literature review a significant number of articles have been published on 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid.

Structure

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

7a,12a-Dihydroxy-3-oxo-4-cholenoic acid.mol
  Mrv0541 02231218322D          

 32 35  0  0  0  0            999 V2000
   -2.5040   -2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5040   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -1.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -2.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750   -2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -2.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -2.5001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3539   -1.6751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0684   -1.2626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8530   -1.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3379   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8530   -0.1826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1079    0.6020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5888    1.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8844    2.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993    2.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149    0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -0.4376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0684    0.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.0251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3606   -0.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -1.2626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0750   -1.6751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0750   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9949    2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2184    1.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    0.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -2.0876    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.8501    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -2.0876    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  2  0  0  0  0
  5  6  1  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
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 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  2  0  0  0  0
 20 28  1  6  0  0  0
  7 29  1  6  0  0  0
 22 30  1  6  0  0  0
  8 31  1  1  0  0  0
  9 32  1  6  0  0  0
M  END

HMDB0000447
     RDKit          3D
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid
 65 68  0  0  0  0  0  0  0  0999 V2000
    3.3753   -1.8576   -0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4838   -0.3224   -0.4026 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8070   -0.2211    0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2582    1.1362    0.7440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6324    1.0273    1.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1806   -0.0796    1.4645 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2350    2.1649    1.8436 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    0.0793    0.3552 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2671    1.5657    0.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763    2.0640    0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869    0.8053    0.4149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2979    0.8058   -0.0546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9262   -0.5183    0.2976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0825   -1.6954    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3756   -1.5550    0.2869 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7341   -1.7495    1.6312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -0.2501   -0.2365 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9027   -0.2775   -1.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2459   -0.5884   -0.4487 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0555   -0.4788   -1.9374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0361   -1.8164   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2878   -1.8566   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8170   -0.5008   -1.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6792   -0.3326   -2.0898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3187    0.6186   -0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0475    0.5953   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5144    1.6991    0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419    1.8554    0.8011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5128    1.8600    2.0990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1515   -2.4161    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4210   -2.1918   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7768   -2.0495   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402    0.1443   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471   -0.9577    1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6413   -0.6125   -0.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5900    1.6308    1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3734    1.8398   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7589    2.8270    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -0.4526    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.7585    1.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9528    2.1513   -0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    2.8183    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    2.4452   -0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963    0.5840    1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949    1.1252   -1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066   -0.4778    1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2583   -2.1236   -0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -2.5255    0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668   -2.3732   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263   -2.5530    1.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386    0.0366   -2.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5647   -1.2783   -2.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    0.3960   -2.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061    0.5749   -2.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8187   -1.0903   -2.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0287   -0.7520   -2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167   -1.6762    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3985   -2.7092   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2120   -2.4190   -1.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1097   -2.3753   -0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9952    1.4264   -0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682    1.5582    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236    2.6485    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736    2.8353    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596    2.0563    2.7210 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  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  6
 13 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 17  8  1  0
 26 19  1  0
 17 11  1  0
 28 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
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 22 60  1  0
 25 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  6
 29 65  1  0
M  END

7a,12a-Dihydroxy-3-oxo-4-cholenoic acid.mol
  Mrv0541 02231218322D          

 32 35  0  0  0  0            999 V2000
   -2.5040   -2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5040   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -1.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895   -2.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750   -2.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -2.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -2.5001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3539   -1.6751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0684   -1.2626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8530   -1.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3379   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8530   -0.1826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1079    0.6020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5888    1.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8844    2.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993    2.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149    0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -0.4376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0684    0.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.0251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3606   -0.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -1.2626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0750   -1.6751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0750   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9949    2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2184    1.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    0.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -2.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -2.0876    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.8501    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -2.0876    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  2  0  0  0  0
  5  6  1  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
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 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
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 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  2  0  0  0  0
 20 28  1  6  0  0  0
  7 29  1  6  0  0  0
 22 30  1  6  0  0  0
  8 31  1  1  0  0  0
  9 32  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000447

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h10,13,16-20,22,26-27H,4-9,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

> <INCHI_KEY>
ZZUMXQCSMJCDDC-DFQOQHGMSA-N

> <FORMULA>
C24H36O5

> <MOLECULAR_WEIGHT>
404.5396

> <EXACT_MASS>
404.256274262

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.67251982157674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.6441609233333345

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.137674241562625

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475011880124207

> <JCHEM_PKA_STRONGEST_BASIC>
-0.182516353258798

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
110.58789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000447
     RDKit          3D
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid
 65 68  0  0  0  0  0  0  0  0999 V2000
    3.3753   -1.8576   -0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4838   -0.3224   -0.4026 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8070   -0.2211    0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2582    1.1362    0.7440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6324    1.0273    1.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1806   -0.0796    1.4645 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2350    2.1649    1.8436 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    0.0793    0.3552 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2671    1.5657    0.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763    2.0640    0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869    0.8053    0.4149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2979    0.8058   -0.0546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9262   -0.5183    0.2976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0825   -1.6954    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3756   -1.5550    0.2869 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7341   -1.7495    1.6312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -0.2501   -0.2365 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9027   -0.2775   -1.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2459   -0.5884   -0.4487 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0555   -0.4788   -1.9374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0361   -1.8164   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2878   -1.8566   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8170   -0.5008   -1.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6792   -0.3326   -2.0898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3187    0.6186   -0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0475    0.5953   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5144    1.6991    0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419    1.8554    0.8011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5128    1.8600    2.0990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1515   -2.4161    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4210   -2.1918   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7768   -2.0495   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402    0.1443   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471   -0.9577    1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6413   -0.6125   -0.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5900    1.6308    1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3734    1.8398   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7589    2.8270    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -0.4526    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.7585    1.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9528    2.1513   -0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    2.8183    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    2.4452   -0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963    0.5840    1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949    1.1252   -1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066   -0.4778    1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2583   -2.1236   -0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -2.5255    0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668   -2.3732   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263   -2.5530    1.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386    0.0366   -2.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5647   -1.2783   -2.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    0.3960   -2.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061    0.5749   -2.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8187   -1.0903   -2.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0287   -0.7520   -2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167   -1.6762    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3985   -2.7092   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2120   -2.4190   -1.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1097   -2.3753   -0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9952    1.4264   -0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682    1.5582    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236    2.6485    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736    2.8353    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596    2.0563    2.7210 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  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  6
 13 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 17  8  1  0
 26 19  1  0
 17 11  1  0
 28 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 25 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  6
 29 65  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid.mol       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.674  -4.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.674  -3.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.340  -2.357   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.340  -5.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.007  -4.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.673  -5.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.661  -4.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.661  -3.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.994  -2.357   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.459  -2.833   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.364  -1.587   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.459  -0.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.935   1.124   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.966   2.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.518   3.758   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.039   3.999   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.441   1.444   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.994  -0.817   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.994   0.723   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.661  -0.047   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.673  -0.817   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.673  -2.357   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.007  -3.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.007  -1.587   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.590   5.437   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.008   2.802   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.008  -5.437   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.661   1.493   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.994  -5.437   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      -0.673  -3.897   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.661  -1.587   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.994  -3.897   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   29                                                  
CONECT    8    7    9   22   31                                             
CONECT    9    8   10   18   32                                             
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   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21    8   23   30                                             
CONECT   23   22    3    5   24                                             
CONECT   24   23                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27    1                                                            
CONECT   28   20                                                            
CONECT   29    7                                                            
CONECT   30   22                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0000447
HETATM    1  C1  UNL     1       3.375  -1.858  -0.680  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.484  -0.322  -0.403  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.807  -0.221   0.316  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.258   1.136   0.744  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.632   1.027   1.379  1.00  0.00           C  
HETATM    6  O1  UNL     1       7.181  -0.080   1.465  1.00  0.00           O  
HETATM    7  O2  UNL     1       7.235   2.165   1.844  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.287   0.079   0.355  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.267   1.566   0.632  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.876   2.064   0.212  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.087   0.805   0.415  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.298   0.806  -0.055  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.926  -0.518   0.298  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.082  -1.695   0.054  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.376  -1.555   0.287  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.734  -1.749   1.631  1.00  0.00           O  
HETATM   17  C14 UNL     1       0.944  -0.250  -0.236  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.903  -0.278  -1.718  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.246  -0.588  -0.449  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.056  -0.479  -1.937  1.00  0.00           C  
HETATM   21  C18 UNL     1      -4.036  -1.816  -0.051  1.00  0.00           C  
HETATM   22  C19 UNL     1      -5.288  -1.857  -0.860  1.00  0.00           C  
HETATM   23  C20 UNL     1      -5.817  -0.501  -1.167  1.00  0.00           C  
HETATM   24  O4  UNL     1      -6.679  -0.333  -2.090  1.00  0.00           O  
HETATM   25  C21 UNL     1      -5.319   0.619  -0.383  1.00  0.00           C  
HETATM   26  C22 UNL     1      -4.048   0.595  -0.016  1.00  0.00           C  
HETATM   27  C23 UNL     1      -3.514   1.699   0.774  1.00  0.00           C  
HETATM   28  C24 UNL     1      -2.042   1.855   0.801  1.00  0.00           C  
HETATM   29  O5  UNL     1      -1.513   1.860   2.099  1.00  0.00           O  
HETATM   30  H1  UNL     1       3.151  -2.416   0.216  1.00  0.00           H  
HETATM   31  H2  UNL     1       4.421  -2.192  -0.978  1.00  0.00           H  
HETATM   32  H3  UNL     1       2.777  -2.049  -1.580  1.00  0.00           H  
HETATM   33  H4  UNL     1       3.640   0.144  -1.385  1.00  0.00           H  
HETATM   34  H5  UNL     1       4.847  -0.958   1.176  1.00  0.00           H  
HETATM   35  H6  UNL     1       5.641  -0.612  -0.351  1.00  0.00           H  
HETATM   36  H7  UNL     1       4.590   1.631   1.493  1.00  0.00           H  
HETATM   37  H8  UNL     1       5.373   1.840  -0.096  1.00  0.00           H  
HETATM   38  H9  UNL     1       7.759   2.827   1.269  1.00  0.00           H  
HETATM   39  H10 UNL     1       2.340  -0.453   1.352  1.00  0.00           H  
HETATM   40  H11 UNL     1       2.335   1.759   1.715  1.00  0.00           H  
HETATM   41  H12 UNL     1       2.953   2.151  -0.006  1.00  0.00           H  
HETATM   42  H13 UNL     1       0.511   2.818   0.935  1.00  0.00           H  
HETATM   43  H14 UNL     1       0.843   2.445  -0.804  1.00  0.00           H  
HETATM   44  H15 UNL     1       0.096   0.584   1.505  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.495   1.125  -1.083  1.00  0.00           H  
HETATM   46  H17 UNL     1      -2.207  -0.478   1.389  1.00  0.00           H  
HETATM   47  H18 UNL     1      -1.258  -2.124  -0.977  1.00  0.00           H  
HETATM   48  H19 UNL     1      -1.444  -2.525   0.734  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.867  -2.373  -0.277  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.226  -2.553   1.923  1.00  0.00           H  
HETATM   51  H22 UNL     1       1.839   0.037  -2.232  1.00  0.00           H  
HETATM   52  H23 UNL     1       0.565  -1.278  -2.058  1.00  0.00           H  
HETATM   53  H24 UNL     1       0.057   0.396  -2.054  1.00  0.00           H  
HETATM   54  H25 UNL     1      -3.206   0.575  -2.307  1.00  0.00           H  
HETATM   55  H26 UNL     1      -3.819  -1.090  -2.470  1.00  0.00           H  
HETATM   56  H27 UNL     1      -2.029  -0.752  -2.271  1.00  0.00           H  
HETATM   57  H28 UNL     1      -4.317  -1.676   1.024  1.00  0.00           H  
HETATM   58  H29 UNL     1      -3.398  -2.709  -0.206  1.00  0.00           H  
HETATM   59  H30 UNL     1      -5.212  -2.419  -1.806  1.00  0.00           H  
HETATM   60  H31 UNL     1      -6.110  -2.375  -0.283  1.00  0.00           H  
HETATM   61  H32 UNL     1      -5.995   1.426  -0.129  1.00  0.00           H  
HETATM   62  H33 UNL     1      -3.868   1.558   1.834  1.00  0.00           H  
HETATM   63  H34 UNL     1      -4.024   2.649   0.445  1.00  0.00           H  
HETATM   64  H35 UNL     1      -1.774   2.835   0.360  1.00  0.00           H  
HETATM   65  H36 UNL     1      -2.260   2.056   2.721  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    8   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6    6    7
CONECT    7   38
CONECT    8    9   17   39
CONECT    9   10   40   41
CONECT   10   11   42   43
CONECT   11   12   17   44
CONECT   12   13   28   45
CONECT   13   14   19   46
CONECT   14   15   47   48
CONECT   15   16   17   49
CONECT   16   50
CONECT   17   18
CONECT   18   51   52   53
CONECT   19   20   21   26
CONECT   20   54   55   56
CONECT   21   22   57   58
CONECT   22   23   59   60
CONECT   23   24   24   25
CONECT   25   26   26   61
CONECT   26   27
CONECT   27   28   62   63
CONECT   28   29   64
CONECT   29   65
END

HMDB0000447
     RDKit          3D
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid
 65 68  0  0  0  0  0  0  0  0999 V2000
    3.3753   -1.8576   -0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4838   -0.3224   -0.4026 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8070   -0.2211    0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2582    1.1362    0.7440 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6324    1.0273    1.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1806   -0.0796    1.4645 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2350    2.1649    1.8436 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    0.0793    0.3552 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2671    1.5657    0.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763    2.0640    0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869    0.8053    0.4149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2979    0.8058   -0.0546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9262   -0.5183    0.2976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0825   -1.6954    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3756   -1.5550    0.2869 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7341   -1.7495    1.6312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -0.2501   -0.2365 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9027   -0.2775   -1.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2459   -0.5884   -0.4487 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0555   -0.4788   -1.9374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0361   -1.8164   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2878   -1.8566   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8170   -0.5008   -1.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6792   -0.3326   -2.0898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3187    0.6186   -0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0475    0.5953   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5144    1.6991    0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419    1.8554    0.8011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5128    1.8600    2.0990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1515   -2.4161    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4210   -2.1918   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7768   -2.0495   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402    0.1443   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471   -0.9577    1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6413   -0.6125   -0.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5900    1.6308    1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3734    1.8398   -0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7589    2.8270    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -0.4526    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.7585    1.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9528    2.1513   -0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    2.8183    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    2.4452   -0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963    0.5840    1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949    1.1252   -1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066   -0.4778    1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2583   -2.1236   -0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -2.5255    0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668   -2.3732   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263   -2.5530    1.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386    0.0366   -2.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5647   -1.2783   -2.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    0.3960   -2.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061    0.5749   -2.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8187   -1.0903   -2.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0287   -0.7520   -2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167   -1.6762    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3985   -2.7092   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2120   -2.4190   -1.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1097   -2.3753   -0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9952    1.4264   -0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682    1.5582    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236    2.6485    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7736    2.8353    0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596    2.0563    2.7210 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  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  6
 13 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 17  8  1  0
 26 19  1  0
 17 11  1  0
 28 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 25 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  6
 29 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7alpha,12alpha-Dihydroxy-3-oxochol-4-enoate	ChEBI
7alpha,12alpha-Dihydroxy-3-oxochol-4-enoic acid	ChEBI
7a,12a-Dihydroxy-3-oxochol-4-enoate	Generator
7a,12a-Dihydroxy-3-oxochol-4-enoic acid	Generator
7Α,12α-dihydroxy-3-oxochol-4-enoate	Generator
7Α,12α-dihydroxy-3-oxochol-4-enoic acid	Generator
7a,12a-Dihydroxy-3-oxo-4-cholenoate	Generator
7a,12a-Dihydroxy-3-oxo-chol-4-en-24-Oate	HMDB
7a,12a-Dihydroxy-3-oxo-chol-4-en-24-Oic acid	HMDB
(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-Dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoate	Generator, HMDB

Chemical Formula

C₂₄H₃₆O₅

Average Molecular Weight

404.5396

Monoisotopic Molecular Weight

404.256274262

IUPAC Name

(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid

CAS Registry Number

13587-11-6

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C24H36O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h10,13,16-20,22,26-27H,4-9,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

InChI Key

ZZUMXQCSMJCDDC-DFQOQHGMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
3-oxo-delta-4-steroid
3-oxosteroid
7-hydroxysteroid
Oxosteroid
12-hydroxysteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

7alpha-hydroxy steroid (CHEBI:49269 )
3-oxo Delta(4)-steroid (CHEBI:49269 )
12alpha-hydroxy steroid (CHEBI:49269 )
C24 bile acids, alcohols, and derivatives (LMST04010241 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000447)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000447)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000447)

Source

Endogenous

Endogenous (HMDB: HMDB0000447)

Animal

Animal (HMDB: HMDB0000447)

Exogenous

Food

Food (HMDB: HMDB0000447)

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: HMDB0000447)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000447)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000447)

Lipid metabolism pathway (HMDB: HMDB0000447)

Cellular process

Cell signaling (HMDB: HMDB0000447)

Biochemical process

Lipid transport (HMDB: HMDB0000447)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000447)

Molecular messenger

Signaling molecule (HMDB: HMDB0000447)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000447)

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	0.029 g/L	ALOGPS
logP	2.17	ALOGPS
logP	2.64	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.18	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.59 m³·mol⁻¹	ChemAxon
Polarizability	45.67 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]+	194.258	31661259
DarkChem	[M-H]-	186.782	31661259
AllCCS	[M+H]+	201.655	32859911
AllCCS	[M-H]-	201.235	32859911
DeepCCS	[M-2H]-	240.941	30932474
DeepCCS	[M+Na]+	216.014	30932474
AllCCS	[M+H]+	201.7	32859911
AllCCS	[M+H-H2O]+	199.4	32859911
AllCCS	[M+NH4]+	203.7	32859911
AllCCS	[M+Na]+	204.3	32859911
AllCCS	[M-H]-	201.2	32859911
AllCCS	[M+Na-2H]-	202.4	32859911
AllCCS	[M+HCOO]-	203.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.24 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9498 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.5 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2726.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	193.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	194.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	250.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	536.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	572.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1027.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	501.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1493.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	326.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	430.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	259.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	242.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	74.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2=CC(=O)CC[C@]12C	4716.4	Standard polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2=CC(=O)CC[C@]12C	3357.7	Standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2=CC(=O)CC[C@]12C	3774.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,1TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O	3563.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O	3537.2	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,1TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C	3510.4	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,1TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O	3495.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O	3540.0	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C	3495.7	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O	3456.0	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C	3454.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O	3446.4	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TMS,isomer #6	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C	3390.8	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C	3461.6	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,3TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O	3407.4	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,3TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C	3360.2	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,3TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C	3373.2	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,4TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C	3357.1	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,4TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C	3431.6	Standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,4TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C=C1C[C@H]3O[Si](C)(C)C	3533.0	Standard polar	33892256
7a,12a-Dihydroxy-3-oxo-4-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]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O	3815.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O	3764.5	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	3734.5	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,1TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O	3728.4	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-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]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O	3986.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	3937.8	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O	3900.1	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	3899.4	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TBDMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O	3871.8	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,2TBDMS,isomer #6	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	3804.6	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	4120.5	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,3TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O	4027.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,3TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	3970.1	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,3TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	4002.9	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,4TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	4167.0	Semi standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,4TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	4136.3	Standard non polar	33892256
7a,12a-Dihydroxy-3-oxo-4-cholenoic acid,4TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C=C1C[C@H]3O[Si](C)(C)C(C)(C)C	3804.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ei-0669000000-9fed3137295895243d19	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-2311079000-3edbc2a2cd05cbc2b635	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-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 - 7a,12a-Dihydroxy-3-oxo-4-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 - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-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 - 7a,12a-Dihydroxy-3-oxo-4-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 - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 10V, Positive-QTOF	splash10-00kr-0009000000-9790562e687cf6cf1535	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 20V, Positive-QTOF	splash10-014r-0009000000-1c6408067e4a44b9f56e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 40V, Positive-QTOF	splash10-0690-3109000000-719d0cfab7cfaf7880b9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 10V, Negative-QTOF	splash10-0udr-0008900000-f3a5eb21db76b105dbea	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 20V, Negative-QTOF	splash10-0f79-1009300000-b66cd2ec87f94b8a947c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-b8d05ae88868a739f071	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 10V, Negative-QTOF	splash10-0udi-0002900000-ae4a5ddd7a1b0b538dd5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 20V, Negative-QTOF	splash10-0udi-0003900000-f1b9886a70692db58726	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 40V, Negative-QTOF	splash10-0udi-0069100000-8a8f6effc421551ee6f2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 10V, Positive-QTOF	splash10-0ap0-0019500000-c35d3c0bd0a20c4d8f6a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 20V, Positive-QTOF	splash10-00kr-2179000000-db8f311481a2e3288e85	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid 40V, Positive-QTOF	splash10-0a4i-4692000000-ce08e78198538b9723e1	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022052

KNApSAcK ID

Not Available

Chemspider ID

4447084

KEGG Compound ID

C15568

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5436

PubChem Compound

5283996

PDB ID

Not Available

ChEBI ID

49269

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kallner, Anders. Bile acids and steroids. 182. A method of synthesis of allochlanoic acids. Acta Chemica Scandinavica (1947-1973) (1967), 21(2), 322-8.

Material Safety Data Sheet (MSDS)

Not Available

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 ]

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 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid (HMDB0000447)

MOL for HMDB0000447 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

3D MOL for HMDB0000447 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

3D SDF for HMDB0000447 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

3D-SDF for HMDB0000447 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

PDB for HMDB0000447 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

3D PDB for HMDB0000447 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

SMILES for HMDB0000447 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

INCHI for HMDB0000447 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

Structure for HMDB0000447 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

3D Structure for HMDB0000447 (7a,12a-Dihydroxy-3-oxo-4-cholenoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References