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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 02:49:00 UTC

HMDB ID

HMDB0000328

Secondary Accession Numbers

HMDB00328

Metabolite Identification

Common Name

12-Ketodeoxycholic acid

Description

12-Ketodeoxycholic acid is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending 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 ).

Structure

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


  Mrv0541 02231218272D          

 33 36  0  0  1  0            999 V2000
   14.4630  -11.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7283  -14.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3413   -9.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6360  -10.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4630  -13.5017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -13.0892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7486  -13.0892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -12.2641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9979  -13.5074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9912  -14.3666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9580  -12.0128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4763  -14.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9580  -13.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7486  -12.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7354  -14.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4395  -12.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4630  -11.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2332  -13.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2195  -14.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2144  -11.2287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -11.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0043  -12.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4513  -13.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4444  -14.3725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0215  -11.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6634  -10.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2779  -10.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0852  -10.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0372  -13.8272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2473  -13.7454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3201  -12.7592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9938  -15.0265    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6101  -11.9105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  2  0  0  0  0
 24  2  1  6  0  0  0
  3 28  1  0  0  0  0
  4 28  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 12  1  0  0  0  0
  5 29  1  1  0  0  0
  6  8  1  0  0  0  0
  6 13  1  0  0  0  0
  6 30  1  6  0  0  0
  7  9  1  0  0  0  0
  7 14  1  0  0  0  0
  7 31  1  6  0  0  0
  8 11  1  0  0  0  0
  8 17  1  0  0  0  0
  8 21  1  1  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
  9 22  1  1  0  0  0
 10 15  1  0  0  0  0
 10 19  1  0  0  0  0
 10 32  1  1  0  0  0
 11 16  1  0  0  0  0
 11 20  1  0  0  0  0
 11 33  1  6  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
 18 23  1  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 20 26  1  6  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0000328
     RDKit          3D
12-Ketodeoxycholic acid
 66 69  0  0  0  0  0  0  0  0999 V2000
    4.3475    0.6229    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630   -0.6680    0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2189   -0.8838   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -0.8934   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -1.9620    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7572   -3.1189    0.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2174   -1.8091    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3306   -0.9169    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9960   -0.8769    2.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    0.0554    2.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.3265    1.3028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1238    0.3655    0.8882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2386   -0.0942    1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5800    0.4099    1.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9210    0.4496    0.0375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6736   -0.8006   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4114   -0.4389   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4679   -1.5375   -2.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6381    0.6541   -2.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    0.3440   -2.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483    0.6751   -0.8746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4403    2.1569   -0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -0.1361   -0.4640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4823   -0.2322   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030   -0.8682   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1930   -1.8601   -1.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794   -0.1831    0.3209 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4999    1.2429   -0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4335    0.4688    1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    1.3250    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8700    1.1495    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -1.4603    1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9714   -0.0373   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569   -1.8828   -1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1498   -1.0984   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1345    0.1083   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0885   -1.3717    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -2.0090    0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7411   -0.4588    3.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -1.8454    2.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.1862    3.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803    1.1018    2.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394   -1.4329    1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    1.4570    0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659    0.2726    2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857   -1.2136    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304   -0.2874    1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401    1.3913    2.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6307    1.2886   -0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951   -1.6580   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4408   -0.9945    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4262   -0.0517   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9641   -1.4141   -3.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9426    0.6346   -3.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8886    1.6503   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9943   -0.7361   -2.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5275    0.9513   -2.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398    2.6031    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1716    2.7186   -1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533    2.3562   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.1963   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449    0.7409   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609   -0.8970   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344    1.8207   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8735    1.2645   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628    1.8348    0.5498 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
 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  2  0
 25 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  0
 16 51  1  0
 17 52  1  1
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  1
 24 62  1  0
 24 63  1  0
 28 64  1  0
 28 65  1  0
 28 66  1  0
M  END


  Mrv0541 02231218272D          

 33 36  0  0  1  0            999 V2000
   14.4630  -11.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7283  -14.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3413   -9.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6360  -10.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4630  -13.5017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -13.0892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7486  -13.0892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -12.2641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9979  -13.5074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9912  -14.3666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9580  -12.0128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4763  -14.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9580  -13.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7486  -12.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7354  -14.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4395  -12.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4630  -11.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2332  -13.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2195  -14.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2144  -11.2287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -11.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0043  -12.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4513  -13.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4444  -14.3725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0215  -11.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6634  -10.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2779  -10.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0852  -10.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0372  -13.8272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2473  -13.7454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3201  -12.7592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9938  -15.0265    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6101  -11.9105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  2  0  0  0  0
 24  2  1  6  0  0  0
  3 28  1  0  0  0  0
  4 28  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 12  1  0  0  0  0
  5 29  1  1  0  0  0
  6  8  1  0  0  0  0
  6 13  1  0  0  0  0
  6 30  1  6  0  0  0
  7  9  1  0  0  0  0
  7 14  1  0  0  0  0
  7 31  1  6  0  0  0
  8 11  1  0  0  0  0
  8 17  1  0  0  0  0
  8 21  1  1  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
  9 22  1  1  0  0  0
 10 15  1  0  0  0  0
 10 19  1  0  0  0  0
 10 32  1  1  0  0  0
 11 16  1  0  0  0  0
 11 20  1  0  0  0  0
 11 33  1  6  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
 18 23  1  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 20 26  1  6  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000328

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1

> <INCHI_KEY>
CVNYHSDFZXHMMJ-VPUMZWJWSA-N

> <FORMULA>
C24H38O4

> <MOLECULAR_WEIGHT>
390.5561

> <EXACT_MASS>
390.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.515900800801035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
4.3547869593333335

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296396219790154

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.556916959655809

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569565006749031

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
108.37449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-ketolithocholic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000328
     RDKit          3D
12-Ketodeoxycholic acid
 66 69  0  0  0  0  0  0  0  0999 V2000
    4.3475    0.6229    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630   -0.6680    0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2189   -0.8838   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -0.8934   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -1.9620    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7572   -3.1189    0.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2174   -1.8091    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3306   -0.9169    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9960   -0.8769    2.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    0.0554    2.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.3265    1.3028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1238    0.3655    0.8882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2386   -0.0942    1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5800    0.4099    1.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9210    0.4496    0.0375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6736   -0.8006   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4114   -0.4389   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4679   -1.5375   -2.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6381    0.6541   -2.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    0.3440   -2.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483    0.6751   -0.8746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4403    2.1569   -0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -0.1361   -0.4640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4823   -0.2322   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030   -0.8682   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1930   -1.8601   -1.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794   -0.1831    0.3209 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4999    1.2429   -0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4335    0.4688    1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    1.3250    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8700    1.1495    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -1.4603    1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9714   -0.0373   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569   -1.8828   -1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1498   -1.0984   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1345    0.1083   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0885   -1.3717    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -2.0090    0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7411   -0.4588    3.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -1.8454    2.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.1862    3.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803    1.1018    2.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394   -1.4329    1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    1.4570    0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659    0.2726    2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857   -1.2136    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304   -0.2874    1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401    1.3913    2.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6307    1.2886   -0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951   -1.6580   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4408   -0.9945    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4262   -0.0517   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9641   -1.4141   -3.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9426    0.6346   -3.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8886    1.6503   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9943   -0.7361   -2.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5275    0.9513   -2.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398    2.6031    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1716    2.7186   -1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533    2.3562   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.1963   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449    0.7409   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609   -0.8970   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344    1.8207   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8735    1.2645   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628    1.8348    0.5498 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
 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  2  0
 25 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  0
 16 51  1  0
 17 52  1  1
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  1
 24 62  1  0
 24 63  1  0
 28 64  1  0
 28 65  1  0
 28 66  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      26.998 -20.583   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      20.026 -27.593   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.237 -17.398   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      34.787 -20.007   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      26.998 -25.203   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.331 -24.433   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.664 -24.433   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.331 -22.893   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.263 -25.214   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.250 -26.818   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.788 -22.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.022 -26.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.788 -24.902   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.664 -22.893   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.639 -27.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.687 -23.663   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.998 -22.123   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.835 -24.345   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.810 -27.664   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.267 -20.960   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.331 -21.353   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.275 -23.674   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.376 -25.158   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.363 -26.829   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.773 -20.643   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.238 -19.814   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.252 -19.179   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      33.759 -18.861   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      28.069 -25.811   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      28.462 -25.658   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      26.731 -23.817   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      24.255 -28.049   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      31.006 -22.233   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   24                                                            
CONECT    3   28                                                            
CONECT    4   28                                                            
CONECT    5    6    7   12   29                                             
CONECT    6    5    8   13   30                                             
CONECT    7    5    9   14   31                                             
CONECT    8    6   11   17   21                                             
CONECT    9    7   10   18   22                                             
CONECT   10    9   15   19   32                                             
CONECT   11    8   16   20   33                                             
CONECT   12    5   15                                                       
CONECT   13    6   16                                                       
CONECT   14    7   17                                                       
CONECT   15   10   12                                                       
CONECT   16   11   13                                                       
CONECT   17    1    8   14                                                  
CONECT   18    9   23                                                       
CONECT   19   10   24                                                       
CONECT   20   11   25   26                                                  
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   18   24                                                       
CONECT   24    2   19   23                                                  
CONECT   25   20   27                                                       
CONECT   26   20                                                            
CONECT   27   25   28                                                       
CONECT   28    3    4   27                                                  
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000328
HETATM    1  C1  UNL     1       4.347   0.623   1.185  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.763  -0.668   0.735  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.219  -0.884  -0.706  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.768  -0.893  -0.638  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.261  -1.962   0.232  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.757  -3.119   0.061  1.00  0.00           O  
HETATM    7  O2  UNL     1       7.217  -1.809   1.211  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.331  -0.917   1.004  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.996  -0.877   2.475  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.764   0.055   2.564  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.102  -0.326   1.303  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.124   0.366   0.888  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.239  -0.094   1.845  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.580   0.410   1.483  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.921   0.450   0.037  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.674  -0.801  -0.428  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.411  -0.439  -1.719  1.00  0.00           C  
HETATM   18  O3  UNL     1      -5.468  -1.538  -2.561  1.00  0.00           O  
HETATM   19  C16 UNL     1      -4.638   0.654  -2.458  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.180   0.344  -2.298  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.748   0.675  -0.875  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.440   2.157  -0.852  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.572  -0.136  -0.464  1.00  0.00           C  
HETATM   24  C21 UNL     1      -0.482  -0.232  -1.486  1.00  0.00           C  
HETATM   25  C22 UNL     1       0.703  -0.868  -0.886  1.00  0.00           C  
HETATM   26  O4  UNL     1       1.193  -1.860  -1.306  1.00  0.00           O  
HETATM   27  C23 UNL     1       1.279  -0.183   0.321  1.00  0.00           C  
HETATM   28  C24 UNL     1       1.500   1.243  -0.056  1.00  0.00           C  
HETATM   29  H1  UNL     1       5.434   0.469   1.508  1.00  0.00           H  
HETATM   30  H2  UNL     1       4.445   1.325   0.330  1.00  0.00           H  
HETATM   31  H3  UNL     1       3.870   1.149   2.001  1.00  0.00           H  
HETATM   32  H4  UNL     1       4.340  -1.460   1.304  1.00  0.00           H  
HETATM   33  H5  UNL     1       3.971  -0.037  -1.344  1.00  0.00           H  
HETATM   34  H6  UNL     1       3.957  -1.883  -1.091  1.00  0.00           H  
HETATM   35  H7  UNL     1       6.150  -1.098  -1.671  1.00  0.00           H  
HETATM   36  H8  UNL     1       6.135   0.108  -0.364  1.00  0.00           H  
HETATM   37  H9  UNL     1       8.088  -1.372   1.006  1.00  0.00           H  
HETATM   38  H10 UNL     1       2.148  -2.009   0.716  1.00  0.00           H  
HETATM   39  H11 UNL     1       2.741  -0.459   3.131  1.00  0.00           H  
HETATM   40  H12 UNL     1       1.661  -1.845   2.888  1.00  0.00           H  
HETATM   41  H13 UNL     1       0.168  -0.186   3.460  1.00  0.00           H  
HETATM   42  H14 UNL     1       1.080   1.102   2.583  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.139  -1.433   1.332  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.115   1.457   0.982  1.00  0.00           H  
HETATM   45  H17 UNL     1      -1.966   0.273   2.856  1.00  0.00           H  
HETATM   46  H18 UNL     1      -2.186  -1.214   1.876  1.00  0.00           H  
HETATM   47  H19 UNL     1      -4.330  -0.287   1.961  1.00  0.00           H  
HETATM   48  H20 UNL     1      -3.740   1.391   2.015  1.00  0.00           H  
HETATM   49  H21 UNL     1      -4.631   1.289  -0.117  1.00  0.00           H  
HETATM   50  H22 UNL     1      -3.995  -1.658  -0.588  1.00  0.00           H  
HETATM   51  H23 UNL     1      -5.441  -0.994   0.352  1.00  0.00           H  
HETATM   52  H24 UNL     1      -6.426  -0.052  -1.469  1.00  0.00           H  
HETATM   53  H25 UNL     1      -4.964  -1.414  -3.406  1.00  0.00           H  
HETATM   54  H26 UNL     1      -4.943   0.635  -3.537  1.00  0.00           H  
HETATM   55  H27 UNL     1      -4.889   1.650  -2.088  1.00  0.00           H  
HETATM   56  H28 UNL     1      -2.994  -0.736  -2.437  1.00  0.00           H  
HETATM   57  H29 UNL     1      -2.528   0.951  -2.950  1.00  0.00           H  
HETATM   58  H30 UNL     1      -2.540   2.603   0.147  1.00  0.00           H  
HETATM   59  H31 UNL     1      -3.172   2.719  -1.504  1.00  0.00           H  
HETATM   60  H32 UNL     1      -1.453   2.356  -1.264  1.00  0.00           H  
HETATM   61  H33 UNL     1      -1.925  -1.196  -0.300  1.00  0.00           H  
HETATM   62  H34 UNL     1      -0.245   0.741  -1.963  1.00  0.00           H  
HETATM   63  H35 UNL     1      -0.861  -0.897  -2.294  1.00  0.00           H  
HETATM   64  H36 UNL     1       0.534   1.821  -0.107  1.00  0.00           H  
HETATM   65  H37 UNL     1       1.873   1.264  -1.118  1.00  0.00           H  
HETATM   66  H38 UNL     1       2.163   1.835   0.550  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    8   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6    6    7
CONECT    7   37
CONECT    8    9   27   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   27   43
CONECT   12   13   23   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   21   49
CONECT   16   17   50   51
CONECT   17   18   19   52
CONECT   18   53
CONECT   19   20   54   55
CONECT   20   21   56   57
CONECT   21   22   23
CONECT   22   58   59   60
CONECT   23   24   61
CONECT   24   25   62   63
CONECT   25   26   26   27
CONECT   27   28
CONECT   28   64   65   66
END

HMDB0000328
     RDKit          3D
12-Ketodeoxycholic acid
 66 69  0  0  0  0  0  0  0  0999 V2000
    4.3475    0.6229    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630   -0.6680    0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2189   -0.8838   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -0.8934   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -1.9620    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7572   -3.1189    0.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2174   -1.8091    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3306   -0.9169    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9960   -0.8769    2.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    0.0554    2.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.3265    1.3028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1238    0.3655    0.8882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2386   -0.0942    1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5800    0.4099    1.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9210    0.4496    0.0375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6736   -0.8006   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4114   -0.4389   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4679   -1.5375   -2.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6381    0.6541   -2.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    0.3440   -2.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483    0.6751   -0.8746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4403    2.1569   -0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -0.1361   -0.4640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4823   -0.2322   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030   -0.8682   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1930   -1.8601   -1.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794   -0.1831    0.3209 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4999    1.2429   -0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4335    0.4688    1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    1.3250    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8700    1.1495    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -1.4603    1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9714   -0.0373   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569   -1.8828   -1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1498   -1.0984   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1345    0.1083   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0885   -1.3717    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -2.0090    0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7411   -0.4588    3.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -1.8454    2.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.1862    3.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803    1.1018    2.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394   -1.4329    1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    1.4570    0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659    0.2726    2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857   -1.2136    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304   -0.2874    1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401    1.3913    2.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6307    1.2886   -0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951   -1.6580   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4408   -0.9945    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4262   -0.0517   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9641   -1.4141   -3.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9426    0.6346   -3.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8886    1.6503   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9943   -0.7361   -2.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5275    0.9513   -2.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398    2.6031    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1716    2.7186   -1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533    2.3562   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.1963   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449    0.7409   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609   -0.8970   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344    1.8207   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8735    1.2645   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628    1.8348    0.5498 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
 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  2  0
 25 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  0
 16 51  1  0
 17 52  1  1
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  1
 24 62  1  0
 24 63  1  0
 28 64  1  0
 28 65  1  0
 28 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12-Ketodeoxycholate	Generator
(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oate	HMDB
(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oic acid	HMDB
(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oate	HMDB
(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oic acid	HMDB
12-Dehydrodeoxycholate	HMDB
12-Dehydrodeoxycholic acid	HMDB
12-Ketolithocholate	HMDB
12-Ketolithocholic acid	HMDB
12-oxo-3a-Hydroxy-5b-cholanate	HMDB
12-oxo-3a-Hydroxy-5b-cholanic acid	HMDB
12-Oxolithocholate	HMDB
12-Oxolithocholic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholan-24-Oate	HMDB
3a-Hydroxy-12-oxo-5b-cholan-24-Oic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholanate	HMDB
3a-Hydroxy-12-oxo-5b-cholanic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholanoate	HMDB
3a-Hydroxy-12-oxo-5b-cholanoic acid	HMDB
3-Hydroxy-12-ketocholanoic acid	HMDB
12-Ketolithocholic acid, (3beta,5beta)-isomer	HMDB
3 alpha-Hydroxy-12-keto-5 beta-cholanoic acid	HMDB
(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-Hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB

Chemical Formula

C₂₄H₃₈O₄

Average Molecular Weight

390.5561

Monoisotopic Molecular Weight

390.277009704

IUPAC Name

(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

12-ketolithocholic acid

CAS Registry Number

5130-29-0

SMILES

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

InChI Identifier

InChI=1S/C24H38O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1

InChI Key

CVNYHSDFZXHMMJ-VPUMZWJWSA-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-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
12-oxosteroid
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010155 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Depression (PMID: 35445772)

Alzheimer's Disease (PMID: 30337151)

Cancer

Colorectal cancer (PMID: 21724466)

Digestive system disorder

Gastrointestinal disorder

Chronic diarrhea (PMID: 19900947)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0000328)
Cell membrane (HMDB: HMDB0000328)

Biofluid or Excreta

Urine (HMDB: HMDB0000328)

Tissue substructure

Hepatic tissue (HMDB: HMDB0000328)

Cellular substructure

Extracellular (HMDB: HMDB0000328)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31643938)
Bile (PMID: 31643938)

Excreta

Biofluid or Excreta

Feces (PMID: 31643938)
Urine (PMID: 1112456)

Organ

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000328)

Source

Endogenous

Endogenous (HMDB: HMDB0000328)

Animal

Animal (HMDB: HMDB0000328)

Exogenous

Food

Food (HMDB: HMDB0000328)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000328)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000328)

Cellular process

Cell signaling (HMDB: HMDB0000328)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000328)

Role

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	0.013 g/L	ALOGPS
logP	3.78	ALOGPS
logP	4.35	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.56	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.37 m³·mol⁻¹	ChemAxon
Polarizability	45.52 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]+	190.381	31661259
DarkChem	[M-H]-	187.632	31661259
AllCCS	[M+H]+	199.164	32859911
AllCCS	[M-H]-	199.198	32859911
DeepCCS	[M-2H]-	228.232	30932474
DeepCCS	[M+Na]+	202.09	30932474
AllCCS	[M+H]+	199.2	32859911
AllCCS	[M+H-H2O]+	197.0	32859911
AllCCS	[M+NH4]+	201.2	32859911
AllCCS	[M+Na]+	201.8	32859911
AllCCS	[M-H]-	199.2	32859911
AllCCS	[M+Na-2H]-	200.4	32859911
AllCCS	[M+HCOO]-	201.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12-Ketodeoxycholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O	3587.1	Standard polar	33892256
12-Ketodeoxycholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O	3292.7	Standard non polar	33892256
12-Ketodeoxycholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O	3455.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12-Ketodeoxycholic acid,1TMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC(=O)[C@@]21C	3384.1	Semi standard non polar	33892256
12-Ketodeoxycholic acid,1TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC(=O)[C@@]21C	3345.7	Semi standard non polar	33892256
12-Ketodeoxycholic acid,1TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C)[C@@]21C	3294.8	Semi standard non polar	33892256
12-Ketodeoxycholic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC(=O)[C@@]21C	3312.3	Semi standard non polar	33892256
12-Ketodeoxycholic acid,2TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C)[C@@]21C	3235.1	Semi standard non polar	33892256
12-Ketodeoxycholic acid,2TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C)[C@@]21C	3259.5	Semi standard non polar	33892256
12-Ketodeoxycholic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C)[C@@]21C	3216.9	Semi standard non polar	33892256
12-Ketodeoxycholic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C)[C@@]21C	3184.7	Standard non polar	33892256
12-Ketodeoxycholic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C)[C@@]21C	3603.8	Standard polar	33892256
12-Ketodeoxycholic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC(=O)[C@@]21C	3612.4	Semi standard non polar	33892256
12-Ketodeoxycholic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC(=O)[C@@]21C	3614.3	Semi standard non polar	33892256
12-Ketodeoxycholic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C(C)(C)C)[C@@]21C	3547.5	Semi standard non polar	33892256
12-Ketodeoxycholic 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[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC(=O)[C@@]21C	3820.3	Semi standard non polar	33892256
12-Ketodeoxycholic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C(C)(C)C)[C@@]21C	3678.0	Semi standard non polar	33892256
12-Ketodeoxycholic 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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C(C)(C)C)[C@@]21C	3758.9	Semi standard non polar	33892256
12-Ketodeoxycholic 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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C(C)(C)C)[C@@]21C	3907.2	Semi standard non polar	33892256
12-Ketodeoxycholic 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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C(C)(C)C)[C@@]21C	3606.9	Standard non polar	33892256
12-Ketodeoxycholic 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]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C(C)(C)C)[C@@]21C	3860.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-02wa-0309000000-107696c445ee2097f3ad	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-2200690000-116b9b25c9a86c4f4259	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Ketodeoxycholic acid GC-MS (TBDMS_2_3) - 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 - 12-Ketodeoxycholic acid 40V, Positive-QTOF	splash10-0a4j-0973000000-c05ff42fd008465bafb3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 10V, Positive-QTOF	splash10-006x-0009000000-5dee4fb39c808ac6bd6b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 20V, Positive-QTOF	splash10-0a4i-0009000000-a3abedb65cc015b126a4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 40V, Positive-QTOF	splash10-0a4j-0973000000-27eab1754ab850b5d833	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 10V, Positive-QTOF	splash10-00di-0009000000-8cbf377d4ac0ead7f478	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 20V, Positive-QTOF	splash10-05i0-0009000000-f445f21e6bb19a3e03e2	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 40V, Positive-QTOF	splash10-0400-3519000000-e95ed419ca30aa610aad	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 10V, Negative-QTOF	splash10-000i-0009000000-d2798e61ab8bdbb8b70c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 20V, Negative-QTOF	splash10-00dr-1009000000-08abf1a9cb419252bf5a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-1e75d302e82f8e8c004f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 10V, Positive-QTOF	splash10-0596-0009000000-e1273a9cf6cd8fec5090	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 20V, Positive-QTOF	splash10-05fr-2295000000-496364ed24778803b66a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 40V, Positive-QTOF	splash10-0a4l-9620000000-568df3571bdbbb289061	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 10V, Negative-QTOF	splash10-000i-0009000000-0312986dad14766b7b5a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 20V, Negative-QTOF	splash10-0079-0009000000-9c3b566629f1b019e8c8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Ketodeoxycholic acid 40V, Negative-QTOF	splash10-000i-1079000000-22dd9a5f612d7b635280	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

FDB021953

KNApSAcK ID

Not Available

Chemspider ID

2338365

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5317

PubChem Compound

3080612

PDB ID

Not Available

ChEBI ID

803536

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Suzuki, Yoshinori; Okamura, Akio; Shimomura, Kazuo; Suzuki, Tadayuki. Purification of bile acids. Jpn. Kokai Tokkyo Koho (1985), 6 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Reddy B, Engle A, Katsifis S, Simi B, Bartram HP, Perrino P, Mahan C: Biochemical epidemiology of colon cancer: effect of types of dietary fiber on fecal mutagens, acid, and neutral sterols in healthy subjects. Cancer Res. 1989 Aug 15;49(16):4629-35. [PubMed:2545348 ]
Barker GM, Radley S, Bain I, Davis A, Lawson AM, Keighley MR, Neoptolemos JP: Biliary bile acid profiles in patients with familial adenomatous polyposis before and after colectomy. Br J Surg. 1994 Mar;81(3):441-4. [PubMed:8173925 ]
Andersen E, Karlaganis G, Sjovall J: Altered bile acid profiles in duodenal bile and urine in diabetic subjects. Eur J Clin Invest. 1988 Apr;18(2):166-72. [PubMed:3133222 ]
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 ]

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 12-Ketodeoxycholic acid (HMDB0000328)

MOL for HMDB0000328 (12-Ketodeoxycholic acid)

3D MOL for HMDB0000328 (12-Ketodeoxycholic acid)

3D SDF for HMDB0000328 (12-Ketodeoxycholic acid)

3D-SDF for HMDB0000328 (12-Ketodeoxycholic acid)

PDB for HMDB0000328 (12-Ketodeoxycholic acid)

3D PDB for HMDB0000328 (12-Ketodeoxycholic acid)

SMILES for HMDB0000328 (12-Ketodeoxycholic acid)

INCHI for HMDB0000328 (12-Ketodeoxycholic acid)

Structure for HMDB0000328 (12-Ketodeoxycholic acid)

3D Structure for HMDB0000328 (12-Ketodeoxycholic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References