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

enzymes (1)transporters (8) Show 9 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:01 UTC

HMDB ID

HMDB0000400

Secondary Accession Numbers

HMDB00400

Metabolite Identification

Common Name

3,7-Dihydroxy-12-oxocholanoic acid

Description

3,7-Dihydroxy-12-oxocholanoic 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 02231218302D          

 33 36  0  0  1  0            999 V2000
    9.4750   -5.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4750   -6.8175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1894   -7.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9039   -6.8175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9039   -5.9925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1894   -5.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6184   -7.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3329   -6.8175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6184   -5.5800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0474   -5.5800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0474   -4.7549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3329   -4.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6184   -4.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8320   -5.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3170   -5.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9466   -4.5763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2726   -3.8214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0893   -3.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4152   -2.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2319   -2.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5578   -2.1211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7228   -3.5358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9628   -7.3460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8793   -5.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9039   -7.6397    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0474   -3.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7628   -7.2286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3329   -5.9925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3199   -5.2041    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0822   -6.2944    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3329   -3.5201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7817   -3.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6196   -6.3714    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  5  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13  9  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 11  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
  8 23  1  6  0  0  0
  5 24  1  1  0  0  0
  4 25  1  1  0  0  0
 11 26  1  1  0  0  0
  2 27  1  6  0  0  0
  9 28  1  0  0  0  0
 28  8  1  0  0  0  0
 28 10  1  0  0  0  0
 28 29  1  1  0  0  0
 10 30  1  6  0  0  0
 12 31  2  0  0  0  0
 17 32  1  6  0  0  0
  9 33  1  6  0  0  0
M  END

HMDB0000400
     RDKit          3D
3,7-Dihydroxy-12-oxocholanoic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
    4.7711    0.0234   -1.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307    0.2895   -0.1119 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3507   -0.1119    1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033    0.6838    1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205    2.1271    1.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    2.7369    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5644    2.8954    1.7279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4974   -0.3836   -0.5322 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5962   -1.8826   -0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -2.3443   -0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -1.0941   -0.6000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0423   -1.1806   -0.1335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5809    0.1992    0.1329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7217    1.0690    0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6820    1.0594    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2557    2.0726    0.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801   -0.2753    0.3054 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3443   -1.0062    1.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545    0.0365    0.7233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9390   -1.0528    1.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921    1.2710    1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9488    2.3127    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9607    1.7009   -0.5710 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4423    2.7121   -1.3690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2555    0.6212   -1.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8572   -0.4801   -0.3770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3300   -1.6871   -1.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8737   -1.7258   -1.3064 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4886   -1.1013   -2.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2595   -0.1305   -2.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2692   -0.9288   -0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4725    0.8734   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600    1.3781   -0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6963   -1.1808    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7205    0.0167    2.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3583    0.5358    0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409    0.3427    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9946    3.3949    0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2248    0.0216   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212   -2.1162   -1.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -2.3918    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8801   -2.8195   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9411   -3.0525    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -0.5408   -1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506   -1.8743    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771    0.6942   -0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038    0.8117    2.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0825    2.1156    0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -1.7453    1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3696   -0.2276    2.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971   -1.5776    1.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7673   -0.8265    2.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1624   -2.0447    1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0046   -1.0267    2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7042    1.6874    2.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    0.9862    2.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5041    3.0896    0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457    2.8368   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7320    1.2205    0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4300    2.7448   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    1.0589   -1.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215    0.1511   -2.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8182   -0.7711    0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6632   -2.6236   -0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8447   -1.7668   -2.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625   -2.7890   -1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2614   -1.0111   -3.1009 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  2  0
 15 17  1  0
 17 18  1  1
 13 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  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  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  1
 13 46  1  6
 14 47  1  0
 14 48  1  0
 18 49  1  0
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 20 52  1  0
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 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  1
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  1
 27 64  1  0
 27 65  1  0
 28 66  1  6
 29 67  1  0
M  END


  Mrv0541 02231218302D          

 33 36  0  0  1  0            999 V2000
    9.4750   -5.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4750   -6.8175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1894   -7.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9039   -6.8175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9039   -5.9925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1894   -5.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6184   -7.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3329   -6.8175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6184   -5.5800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0474   -5.5800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0474   -4.7549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3329   -4.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6184   -4.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8320   -5.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3170   -5.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9466   -4.5763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2726   -3.8214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0893   -3.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4152   -2.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2319   -2.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5578   -2.1211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7228   -3.5358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9628   -7.3460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8793   -5.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9039   -7.6397    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0474   -3.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7628   -7.2286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3329   -5.9925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3199   -5.2041    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0822   -6.2944    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3329   -3.5201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7817   -3.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6196   -6.3714    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  5  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13  9  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 11  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
  8 23  1  6  0  0  0
  5 24  1  1  0  0  0
  4 25  1  1  0  0  0
 11 26  1  1  0  0  0
  2 27  1  6  0  0  0
  9 28  1  0  0  0  0
 28  8  1  0  0  0  0
 28 10  1  0  0  0  0
 28 29  1  1  0  0  0
 10 30  1  6  0  0  0
 12 31  2  0  0  0  0
 17 32  1  6  0  0  0
  9 33  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000400

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O5/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/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,22+,23+,24-/m1/s1

> <INCHI_KEY>
MIHNUBCEFJLAGN-DMMBONCOSA-N

> <FORMULA>
C24H38O5

> <MOLECULAR_WEIGHT>
406.5555

> <EXACT_MASS>
406.271924326

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
46.4394192970417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
3.046022162333333

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296339807159416

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.385323492622886

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5149500746765611

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
109.96699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-ketochenodeoxycholic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000400
     RDKit          3D
3,7-Dihydroxy-12-oxocholanoic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
    4.7711    0.0234   -1.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307    0.2895   -0.1119 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3507   -0.1119    1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033    0.6838    1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205    2.1271    1.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    2.7369    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5644    2.8954    1.7279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4974   -0.3836   -0.5322 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5962   -1.8826   -0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -2.3443   -0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -1.0941   -0.6000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0423   -1.1806   -0.1335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5809    0.1992    0.1329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7217    1.0690    0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6820    1.0594    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2557    2.0726    0.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801   -0.2753    0.3054 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3443   -1.0062    1.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545    0.0365    0.7233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9390   -1.0528    1.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921    1.2710    1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9488    2.3127    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9607    1.7009   -0.5710 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4423    2.7121   -1.3690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2555    0.6212   -1.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8572   -0.4801   -0.3770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3300   -1.6871   -1.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8737   -1.7258   -1.3064 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4886   -1.1013   -2.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2595   -0.1305   -2.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2692   -0.9288   -0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4725    0.8734   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600    1.3781   -0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6963   -1.1808    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7205    0.0167    2.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3583    0.5358    0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409    0.3427    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9946    3.3949    0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2248    0.0216   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212   -2.1162   -1.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -2.3918    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8801   -2.8195   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9411   -3.0525    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -0.5408   -1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506   -1.8743    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771    0.6942   -0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038    0.8117    2.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0825    2.1156    0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -1.7453    1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3696   -0.2276    2.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971   -1.5776    1.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7673   -0.8265    2.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1624   -2.0447    1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0046   -1.0267    2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7042    1.6874    2.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    0.9862    2.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5041    3.0896    0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457    2.8368   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7320    1.2205    0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4300    2.7448   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    1.0589   -1.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215    0.1511   -2.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8182   -0.7711    0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6632   -2.6236   -0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8447   -1.7668   -2.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625   -2.7890   -1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2614   -1.0111   -3.1009 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  2  0
 15 17  1  0
 17 18  1  1
 13 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  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  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  1
 13 46  1  6
 14 47  1  0
 14 48  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  1
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  1
 27 64  1  0
 27 65  1  0
 28 66  1  6
 29 67  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  C   UNK     0      17.687 -11.186   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.687 -12.726   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.020 -13.496   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.354 -12.726   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.354 -11.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.020 -10.416   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.688 -13.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.021 -12.726   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.688 -10.416   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.355 -10.416   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.355  -8.876   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.021  -8.106   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.688  -8.876   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.820 -10.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.725  -9.646   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.034  -8.542   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.642  -7.133   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.167  -6.955   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.775  -5.546   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.300  -5.369   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      30.908  -3.959   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      31.216  -6.600   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      24.197 -13.713   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.308  -9.698   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      20.354 -14.261   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      24.355  -7.336   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.357 -13.493   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      23.021 -11.186   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      22.997  -9.714   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      24.420 -11.750   0.000  0.00  0.00           H+0
HETATM   31  O   UNK     0      23.021  -6.571   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      25.726  -5.902   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      21.690 -11.893   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   25                                             
CONECT    5    4    6    9   24                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7   23   28                                                  
CONECT    9    5   13   28   33                                             
CONECT   10   11   14   28   30                                             
CONECT   11   10   12   16   26                                             
CONECT   12   11   13   31                                                  
CONECT   13   12    9                                                       
CONECT   14   10   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18   32                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    8                                                            
CONECT   24    5                                                            
CONECT   25    4                                                            
CONECT   26   11                                                            
CONECT   27    2                                                            
CONECT   28    9    8   10   29                                             
CONECT   29   28                                                            
CONECT   30   10                                                            
CONECT   31   12                                                            
CONECT   32   17                                                            
CONECT   33    9                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000400
HETATM    1  C1  UNL     1       4.771   0.023  -1.217  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.731   0.289  -0.112  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.351  -0.112   1.155  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.603   0.684   1.412  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.420   2.127   1.540  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.338   2.737   1.496  1.00  0.00           O  
HETATM    7  O2  UNL     1       6.564   2.895   1.728  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.497  -0.384  -0.532  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.596  -1.883  -0.729  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.126  -2.344  -0.746  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.342  -1.094  -0.600  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.042  -1.181  -0.133  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.581   0.199   0.133  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.722   1.069   0.972  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.682   1.059   0.410  1.00  0.00           C  
HETATM   16  O3  UNL     1       1.256   2.073   0.077  1.00  0.00           O  
HETATM   17  C14 UNL     1       1.280  -0.275   0.305  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.344  -1.006   1.612  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.954   0.036   0.723  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.939  -1.053   1.805  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.492   1.271   1.349  1.00  0.00           C  
HETATM   22  C19 UNL     1      -3.949   2.313   0.382  1.00  0.00           C  
HETATM   23  C20 UNL     1      -4.961   1.701  -0.571  1.00  0.00           C  
HETATM   24  O4  UNL     1      -5.442   2.712  -1.369  1.00  0.00           O  
HETATM   25  C21 UNL     1      -4.256   0.621  -1.344  1.00  0.00           C  
HETATM   26  C22 UNL     1      -3.857  -0.480  -0.377  1.00  0.00           C  
HETATM   27  C23 UNL     1      -3.330  -1.687  -1.049  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.874  -1.726  -1.306  1.00  0.00           C  
HETATM   29  O5  UNL     1      -1.489  -1.101  -2.500  1.00  0.00           O  
HETATM   30  H1  UNL     1       4.259  -0.130  -2.184  1.00  0.00           H  
HETATM   31  H2  UNL     1       5.269  -0.929  -0.936  1.00  0.00           H  
HETATM   32  H3  UNL     1       5.473   0.873  -1.310  1.00  0.00           H  
HETATM   33  H4  UNL     1       3.560   1.378  -0.148  1.00  0.00           H  
HETATM   34  H5  UNL     1       4.696  -1.181   1.052  1.00  0.00           H  
HETATM   35  H6  UNL     1       3.720   0.017   2.058  1.00  0.00           H  
HETATM   36  H7  UNL     1       6.358   0.536   0.589  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.141   0.343   2.325  1.00  0.00           H  
HETATM   38  H9  UNL     1       6.995   3.395   0.937  1.00  0.00           H  
HETATM   39  H10 UNL     1       2.225   0.022  -1.554  1.00  0.00           H  
HETATM   40  H11 UNL     1       3.021  -2.116  -1.742  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.173  -2.392   0.044  1.00  0.00           H  
HETATM   42  H13 UNL     1       0.880  -2.819  -1.729  1.00  0.00           H  
HETATM   43  H14 UNL     1       0.941  -3.052   0.095  1.00  0.00           H  
HETATM   44  H15 UNL     1       0.349  -0.541  -1.577  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.251  -1.874   0.696  1.00  0.00           H  
HETATM   46  H17 UNL     1      -1.677   0.694  -0.876  1.00  0.00           H  
HETATM   47  H18 UNL     1      -0.704   0.812   2.034  1.00  0.00           H  
HETATM   48  H19 UNL     1      -1.083   2.116   0.863  1.00  0.00           H  
HETATM   49  H20 UNL     1       2.146  -1.745   1.683  1.00  0.00           H  
HETATM   50  H21 UNL     1       1.370  -0.228   2.426  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.397  -1.578   1.843  1.00  0.00           H  
HETATM   52  H23 UNL     1      -3.767  -0.826   2.527  1.00  0.00           H  
HETATM   53  H24 UNL     1      -3.162  -2.045   1.391  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.005  -1.027   2.392  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.704   1.687   2.025  1.00  0.00           H  
HETATM   56  H27 UNL     1      -4.336   0.986   2.011  1.00  0.00           H  
HETATM   57  H28 UNL     1      -4.504   3.090   0.971  1.00  0.00           H  
HETATM   58  H29 UNL     1      -3.146   2.837  -0.138  1.00  0.00           H  
HETATM   59  H30 UNL     1      -5.732   1.221   0.062  1.00  0.00           H  
HETATM   60  H31 UNL     1      -6.430   2.745  -1.260  1.00  0.00           H  
HETATM   61  H32 UNL     1      -3.415   1.059  -1.878  1.00  0.00           H  
HETATM   62  H33 UNL     1      -4.921   0.151  -2.096  1.00  0.00           H  
HETATM   63  H34 UNL     1      -4.818  -0.771   0.144  1.00  0.00           H  
HETATM   64  H35 UNL     1      -3.663  -2.624  -0.512  1.00  0.00           H  
HETATM   65  H36 UNL     1      -3.845  -1.767  -2.053  1.00  0.00           H  
HETATM   66  H37 UNL     1      -1.563  -2.789  -1.405  1.00  0.00           H  
HETATM   67  H38 UNL     1      -2.261  -1.011  -3.101  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   16   17
CONECT   17   18
CONECT   18   49   50   51
CONECT   19   20   21   26
CONECT   20   52   53   54
CONECT   21   22   55   56
CONECT   22   23   57   58
CONECT   23   24   25   59
CONECT   24   60
CONECT   25   26   61   62
CONECT   26   27   63
CONECT   27   28   64   65
CONECT   28   29   66
CONECT   29   67
END

HMDB0000400
     RDKit          3D
3,7-Dihydroxy-12-oxocholanoic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
    4.7711    0.0234   -1.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307    0.2895   -0.1119 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3507   -0.1119    1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033    0.6838    1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205    2.1271    1.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    2.7369    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5644    2.8954    1.7279 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4974   -0.3836   -0.5322 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5962   -1.8826   -0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -2.3443   -0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -1.0941   -0.6000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0423   -1.1806   -0.1335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5809    0.1992    0.1329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7217    1.0690    0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6820    1.0594    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2557    2.0726    0.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801   -0.2753    0.3054 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3443   -1.0062    1.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545    0.0365    0.7233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9390   -1.0528    1.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921    1.2710    1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9488    2.3127    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9607    1.7009   -0.5710 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4423    2.7121   -1.3690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2555    0.6212   -1.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8572   -0.4801   -0.3770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3300   -1.6871   -1.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8737   -1.7258   -1.3064 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4886   -1.1013   -2.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2595   -0.1305   -2.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2692   -0.9288   -0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4725    0.8734   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600    1.3781   -0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6963   -1.1808    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7205    0.0167    2.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3583    0.5358    0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409    0.3427    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9946    3.3949    0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2248    0.0216   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212   -2.1162   -1.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -2.3918    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8801   -2.8195   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9411   -3.0525    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -0.5408   -1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2506   -1.8743    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771    0.6942   -0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038    0.8117    2.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0825    2.1156    0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -1.7453    1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3696   -0.2276    2.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971   -1.5776    1.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7673   -0.8265    2.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1624   -2.0447    1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0046   -1.0267    2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7042    1.6874    2.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    0.9862    2.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5041    3.0896    0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457    2.8368   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7320    1.2205    0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4300    2.7448   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    1.0589   -1.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215    0.1511   -2.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8182   -0.7711    0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6632   -2.6236   -0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8447   -1.7668   -2.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625   -2.7890   -1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2614   -1.0111   -3.1009 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  2  0
 15 17  1  0
 17 18  1  1
 13 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  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  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  1
 13 46  1  6
 14 47  1  0
 14 48  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  1
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  1
 27 64  1  0
 27 65  1  0
 28 66  1  6
 29 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3alpha,5beta,7alpha)-3,7-Dihydroxy-12-oxocholan-24-Oic acid	ChEBI
3alpha,7alpha-Dihydroxy-12-oxo-5beta-cholanate	ChEBI
(3a,5b,7a)-3,7-Dihydroxy-12-oxocholan-24-Oate	Generator
(3a,5b,7a)-3,7-Dihydroxy-12-oxocholan-24-Oic acid	Generator
(3alpha,5beta,7alpha)-3,7-Dihydroxy-12-oxocholan-24-Oate	Generator
(3Α,5β,7α)-3,7-dihydroxy-12-oxocholan-24-Oate	Generator
(3Α,5β,7α)-3,7-dihydroxy-12-oxocholan-24-Oic acid	Generator
3a,7a-Dihydroxy-12-oxo-5b-cholanate	Generator
3a,7a-Dihydroxy-12-oxo-5b-cholanic acid	Generator
3alpha,7alpha-Dihydroxy-12-oxo-5beta-cholanic acid	Generator
3Α,7α-dihydroxy-12-oxo-5β-cholanate	Generator
3Α,7α-dihydroxy-12-oxo-5β-cholanic acid	Generator
3,7-Dihydroxy-12-oxocholanoate	Generator
(3a,5b,7a)-3,7-Dihydroxy-12-oxo-cholan-24-Oate	HMDB
(3a,5b,7a)-3,7-Dihydroxy-12-oxo-cholan-24-Oic acid	HMDB
12-Keto-3a,7a-dihydroxy-5b-cholanate	HMDB
12-Keto-3a,7a-dihydroxy-5b-cholanic acid	HMDB
12-Keto-chenodeoxycholate	HMDB
12-Keto-chenodeoxycholic acid	HMDB
12-Ketochenodeoxycholate	HMDB
12-Ketochenodeoxycholic acid	HMDB
12-oxo-3a,7a-Dihydroxy-5b-cholan-24-Oate	HMDB
12-oxo-3a,7a-Dihydroxy-5b-cholan-24-Oic acid	HMDB
12-Oxochenodeoxycholate	HMDB
12-Oxochenodeoxycholic acid	HMDB
3a,7a-Dihydroxy-12-keto-5b-cholanate	HMDB
3a,7a-Dihydroxy-12-keto-5b-cholanic acid	HMDB
3a,7a-Dihydroxy-12-ketocholanate	HMDB
3a,7a-Dihydroxy-12-ketocholanic acid	HMDB
3a,7a-Dihydroxy-12-ketocholate	HMDB
3a,7a-Dihydroxy-12-ketocholic acid	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholan-24-Oate	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholan-24-Oic acid	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholanoate	HMDB
3a,7a-Dihydroxy-12-oxo-5b-cholanoic acid	HMDB
3a,7a-Dihydroxy-12-oxocholate	HMDB
3a,7a-Dihydroxy-12-oxocholic acid	HMDB
5b-Cholanic acid-3a,7a-diol-12-one	HMDB
12-Monoketocholate	HMDB
12-Monoketocholic acid	HMDB
12-oxo-3,7-Dihydroxycholanoic acid	HMDB
3 alpha, 7 alpha-Dihydroxy-12-one-5 beta-cholanoic acid	HMDB
3 alpha,7 alpha-Dihydroxy-12-keto-5 beta-cholanoic acid	HMDB
3alpha,7alpha-Dihydroxy-12-keto-5beta-cholanoic acid	HMDB
Sodium monoketocholate	HMDB
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB
3,7-Dihydroxy-12-oxocholanoic acid	ChEBI

Chemical Formula

C₂₄H₃₈O₅

Average Molecular Weight

406.5555

Monoisotopic Molecular Weight

406.271924326

IUPAC Name

(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

12-ketochenodeoxycholic acid

CAS Registry Number

2458-08-4

SMILES

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

InChI Identifier

InChI=1S/C24H38O5/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/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,22+,23+,24-/m1/s1

InChI Key

MIHNUBCEFJLAGN-DMMBONCOSA-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-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
12-oxosteroid
Hydroxysteroid
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

oxo-5beta-cholanic acid (CHEBI:16312 )
C24 bile acids, alcohols, and derivatives (LMST04010176 )

Ontology

Not Available

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	0.042 g/L	ALOGPS
logP	2.56	ALOGPS
logP	3.05	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	-0.51	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	109.97 m³·mol⁻¹	ChemAxon
Polarizability	46.44 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]+	192.585	31661259
DarkChem	[M-H]-	187.826	31661259
AllCCS	[M+H]+	201.792	32859911
AllCCS	[M-H]-	201.192	32859911
DeepCCS	[M-2H]-	234.161	30932474
DeepCCS	[M+Na]+	208.14	30932474
AllCCS	[M+H]+	201.8	32859911
AllCCS	[M+H-H2O]+	199.7	32859911
AllCCS	[M+NH4]+	203.7	32859911
AllCCS	[M+Na]+	204.3	32859911
AllCCS	[M-H]-	201.2	32859911
AllCCS	[M+Na-2H]-	202.5	32859911
AllCCS	[M+HCOO]-	204.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,7-Dihydroxy-12-oxocholanoic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)C(=O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C	3891.6	Standard polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)C(=O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C	3438.5	Standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)C(=O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C	3649.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,7-Dihydroxy-12-oxocholanoic 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](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3458.4	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3385.3	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,1TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3454.7	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,1TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C)[C@@]21C	3327.4	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3424.1	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3342.0	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C)[C@@]21C	3309.1	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,2TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3350.1	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,2TMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C)[C@@]21C	3244.7	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,2TMS,isomer #6	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[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	3272.5	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3344.7	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O)C[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	3271.8	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O[Si](C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C)[C@@]21C	3247.3	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,3TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C[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	3219.1	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O[Si](C)(C)C)C[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	3245.2	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O[Si](C)(C)C)C[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	3275.7	Standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O[Si](C)(C)C)C[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	3550.6	Standard polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3720.4	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3611.3	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3677.6	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,1TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C(C)(C)C)[C@@]21C	3571.4	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3903.9	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3817.2	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C(C)(C)C)[C@@]21C	3777.0	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,2TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3788.5	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,2TBDMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C(C)(C)C)[C@@]21C	3686.8	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,2TBDMS,isomer #6	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[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	3695.8	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4013.6	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O)C[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	3914.1	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C=C(O[Si](C)(C)C(C)(C)C)[C@@]21C	3895.0	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic acid,3TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[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	3878.2	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O[Si](C)(C)C(C)(C)C)C[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	4087.5	Semi standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O[Si](C)(C)C(C)(C)C)C[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	3791.4	Standard non polar	33892256
3,7-Dihydroxy-12-oxocholanoic 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](O[Si](C)(C)C(C)(C)C)C[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	3828.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-0629000000-3135db41ff8b968182b8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-2201198000-bb38056a165602f5feb7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic 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 - 3,7-Dihydroxy-12-oxocholanoic acid 10V, Positive-QTOF	splash10-0079-0009100000-bccc650b1cd4508f1aa7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 20V, Positive-QTOF	splash10-00dr-0009000000-c0c7d7baa207e3cc0a05	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 40V, Positive-QTOF	splash10-056u-1109000000-e710af896d258d339fef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 10V, Negative-QTOF	splash10-0a4r-0008900000-dd8b045786455a7b2b5f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 20V, Negative-QTOF	splash10-052r-1009300000-40bda8fb29d7dc21b644	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-879f42792050e0f3d07a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 10V, Negative-QTOF	splash10-0a4i-0002900000-042ac9446c06cee5ac0f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 20V, Negative-QTOF	splash10-0a4r-0009700000-eec83a5cd15c56ccdff9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 40V, Negative-QTOF	splash10-0udi-1039100000-e4f72f94d4744ca5a96c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 10V, Positive-QTOF	splash10-059i-0009300000-f1bc8868b74d47d136be	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 20V, Positive-QTOF	splash10-0079-1169100000-6bf02d9105b1f9389f99	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,7-Dihydroxy-12-oxocholanoic acid 40V, Positive-QTOF	splash10-0a4i-9561000000-ee15985d116087cd50ec	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Feces

Tissue Locations

Gall Bladder
Intestine
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022017

KNApSAcK ID

Not Available

Chemspider ID

85044

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5389

PubChem Compound

94235

PDB ID

Not Available

ChEBI ID

16312

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Fossati Elena; Polentini Fausto; Carrea Giacomo; Riva Sergio Exploitation of the alcohol dehydrogenase-acetone NADP-regeneration system for the enzymatic preparative-scale production of 12-ketochenodeoxycholic acid. Biotechnology and bioengineering (2006), 93(6), 1216-20.

Material Safety Data Sheet (MSDS)

Not Available

General References

Kuramoto T, Furukawa Y, Nishina T, Sugimoto T, Mahara R, Tohma M, Kihira K, Hoshita T: Identification of short side chain bile acids in urine of patients with cerebrotendinous xanthomatosis. J Lipid Res. 1990 Oct;31(10):1895-902. [PubMed:2079611 ]
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 3,7-Dihydroxy-12-oxocholanoic acid (HMDB0000400)

MOL for HMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)

3D MOL for HMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)

3D SDF for HMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)

3D-SDF for HMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)

PDB for HMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)

3D PDB for HMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)

SMILES for HMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)

INCHI for HMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)

Structure for HMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)

3D Structure for HMDB0000400 (3,7-Dihydroxy-12-oxocholanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

References

References