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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

2022-09-22 18:34:13 UTC

HMDB ID

HMDB0000502

Secondary Accession Numbers

HMDB00502
HMDB0062680
HMDB62680

Metabolite Identification

Common Name

3-Oxocholic acid

Description

3-Oxocholic acid, also known as 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic 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. 3-Oxocholic acid is considered to be practically insoluble (in water) and acidic.

Structure

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


  Mrv1652305041800172D          

 34 37  0  0  0  0            999 V2000
10000.3421 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.340010001.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627010001.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6270 9999.7850    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2001 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2001 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9147 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6292 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.627510000.6159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.913010000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9130 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6275 9998.9658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.342010000.2032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3420 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1266 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6115 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.126610000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.126610001.2832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.842310001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.555910001.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.985110001.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.412910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.842310000.8708    0.0000 H   0  0  0  0  0  0  0  0  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  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
 12  3  2  0  0  0  0
 17  1  1  6  0  0  0
 10 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15  4  1  1  0  0  0
 14  5  1  1  0  0  0
 18  7  1  6  0  0  0
 20 14  1  0  0  0  0
 17 21  1  0  0  0  0
 20  6  1  6  0  0  0
 21  9  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
 26 34  1  6  0  0  0
 27 28  1  0  0  0  0
 27 33  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 26 22  1  0  0  0  0
 26 25  1  0  0  0  0
 18 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22  2  1  1  0  0  0
 23  8  1  6  0  0  0
M  END

HMDB0000502
     RDKit          3D
3-Oxocholic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
    3.6846   -1.5693    1.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462   -0.6808    0.6023 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6953    0.3482    0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0419   -0.3075    0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0381    0.8173    0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0022    1.6609    1.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0438    0.9301   -0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3152    0.1094    0.4516 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4763    0.9069   -0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1770    0.6590   -1.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    0.4361   -0.5032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1106    0.0024   -0.7733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8515    0.1722    0.5620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2246   -0.8657    1.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -0.6408    1.6585 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5462    0.5080    2.3732 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0163   -0.5896    0.3488 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0534   -1.9038   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3241    0.0323    0.4260 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7783   -0.9401    1.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9896    1.3386    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9733    1.8259   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6976    0.7855   -1.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7265    1.1132   -1.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2147   -0.5994   -1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030   -0.5824   -0.8705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1396    0.0799   -2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104    0.7576   -1.8547 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8997    2.1175   -1.6402 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5853   -2.2051    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8955   -0.9869    2.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448   -2.2747    1.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8327   -1.2620   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5761    0.8215    1.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5949    1.1259   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1905   -0.9335    1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2678   -0.9009   -0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7580    1.0641   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    0.8408    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    1.9767   -0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2953    0.4993   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8803    1.5596   -2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3282   -0.1861   -2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2347    1.3689    0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2291   -1.0915   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5581    1.1740    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6874   -0.9190    2.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3245   -1.8469    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035   -1.5040    2.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0307    0.3328    3.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877   -2.3282   -0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.6259    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6436   -1.8566   -1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6695   -0.4805    2.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8891   -1.1086    1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3120   -1.9169    1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5052    1.3397    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175    2.1558    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5098    2.5943   -0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7718    2.4385    0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7244   -1.3145   -0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721   -0.9700   -2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4010   -1.6651   -0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749    0.7545   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9448   -0.7349   -2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750    0.6537   -2.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3864    2.4901   -2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  6
 13 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  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  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 25 61  1  0
 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


  Mrv1652305041800172D          

 34 37  0  0  0  0            999 V2000
10000.3421 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.340010001.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627010001.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6270 9999.7850    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2001 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2001 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9147 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6292 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.627510000.6159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.913010000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9130 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6275 9998.9658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.342010000.2032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3420 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1266 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6115 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.126610000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.126610001.2832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.842310001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.555910001.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.985110001.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.271610002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.412910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.842310000.8708    0.0000 H   0  0  0  0  0  0  0  0  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  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
 12  3  2  0  0  0  0
 17  1  1  6  0  0  0
 10 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15  4  1  1  0  0  0
 14  5  1  1  0  0  0
 18  7  1  6  0  0  0
 20 14  1  0  0  0  0
 17 21  1  0  0  0  0
 20  6  1  6  0  0  0
 21  9  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
 26 34  1  6  0  0  0
 27 28  1  0  0  0  0
 27 33  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 26 22  1  0  0  0  0
 26 25  1  0  0  0  0
 18 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22  2  1  1  0  0  0
 23  8  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000502

> <DATABASE_NAME>
hmdb

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

> <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/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

> <INCHI_KEY>
OEKUSRBIIZNLHZ-DJDNIQJZSA-N

> <FORMULA>
C24H38O5

> <MOLECULAR_WEIGHT>
406.563

> <EXACT_MASS>
406.271924324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
46.231220075041904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.6899952583333335

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.98667664437422

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475012039836772

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1783984748465538

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
109.76119999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000502
     RDKit          3D
3-Oxocholic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
    3.6846   -1.5693    1.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462   -0.6808    0.6023 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6953    0.3482    0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0419   -0.3075    0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0381    0.8173    0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0022    1.6609    1.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0438    0.9301   -0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3152    0.1094    0.4516 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4763    0.9069   -0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1770    0.6590   -1.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    0.4361   -0.5032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1106    0.0024   -0.7733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8515    0.1722    0.5620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2246   -0.8657    1.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -0.6408    1.6585 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5462    0.5080    2.3732 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0163   -0.5896    0.3488 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0534   -1.9038   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3241    0.0323    0.4260 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7783   -0.9401    1.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9896    1.3386    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9733    1.8259   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6976    0.7855   -1.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7265    1.1132   -1.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2147   -0.5994   -1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030   -0.5824   -0.8705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1396    0.0799   -2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104    0.7576   -1.8547 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8997    2.1175   -1.6402 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5853   -2.2051    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8955   -0.9869    2.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448   -2.2747    1.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8327   -1.2620   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5761    0.8215    1.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5949    1.1259   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1905   -0.9335    1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2678   -0.9009   -0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7580    1.0641   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    0.8408    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    1.9767   -0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2953    0.4993   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8803    1.5596   -2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3282   -0.1861   -2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2347    1.3689    0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2291   -1.0915   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5581    1.1740    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6874   -0.9190    2.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3245   -1.8469    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035   -1.5040    2.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0307    0.3328    3.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877   -2.3282   -0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.6259    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6436   -1.8566   -1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6695   -0.4805    2.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8891   -1.1086    1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3120   -1.9169    1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5052    1.3397    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175    2.1558    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5098    2.5943   -0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7718    2.4385    0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7244   -1.3145   -0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721   -0.9700   -2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4010   -1.6651   -0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749    0.7545   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9448   -0.7349   -2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750    0.6537   -2.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3864    2.4901   -2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  6
 13 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  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  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 25 61  1  0
 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                                 04-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-18         0                                  
HETATM    1  O   UNK     0    8667.3058662.405   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8667.3018668.598   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8659.3118662.405   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.3108661.633   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0    8663.3108666.265   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0    8664.6408663.961   0.000  0.00  0.00           H+0
HETATM    7  O   UNK     0    8665.9708669.372   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8667.3018663.961   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8665.9708666.265   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0    8661.9788665.489   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.6448664.719   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8660.6448663.179   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.9788662.409   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.3078664.719   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.3078663.179   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.6418662.409   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.9758663.179   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.9718667.816   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.6388667.046   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.6388665.506   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.9718664.736   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.3058667.046   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.3058665.506   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.7708665.030   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.6758666.276   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.7708667.522   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8668.7708669.062   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8670.1068669.832   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8671.4388669.062   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8672.7748669.832   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0    8674.1068669.062   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0    8672.7748671.372   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0    8667.4378669.832   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0    8670.1068668.292   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   22                                                            
CONECT    3   12                                                            
CONECT    4   15                                                            
CONECT    5   14                                                            
CONECT    6   20                                                            
CONECT    7   18                                                            
CONECT    8   23                                                            
CONECT    9   21                                                            
CONECT   10   11   14                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13    3                                                  
CONECT   13   12   15                                                       
CONECT   14   15   10    5   20                                             
CONECT   15   14   16   13    4                                             
CONECT   16   15   17                                                       
CONECT   17   16    1   21                                                  
CONECT   18   19    7   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   14    6                                             
CONECT   21   20   17    9   23                                             
CONECT   22   23   26   18    2                                             
CONECT   23   22   24   21    8                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   27   34   22   25                                             
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   27                                                            
CONECT   34   26                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0000502
HETATM    1  C1  UNL     1       3.685  -1.569   1.780  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.546  -0.681   0.602  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.695   0.348   0.712  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.042  -0.308   0.688  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.038   0.817   0.795  1.00  0.00           C  
HETATM    6  O1  UNL     1       7.002   1.661   1.713  1.00  0.00           O  
HETATM    7  O2  UNL     1       8.044   0.930  -0.162  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.315   0.109   0.452  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.476   0.907  -0.859  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.177   0.659  -1.624  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.252   0.436  -0.503  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.111   0.002  -0.773  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.852   0.172   0.562  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.225  -0.866   1.469  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.247  -0.641   1.658  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.546   0.508   2.373  1.00  0.00           O  
HETATM   17  C14 UNL     1       1.016  -0.590   0.349  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.053  -1.904  -0.349  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.324   0.032   0.426  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.778  -0.940   1.530  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.990   1.339   0.727  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.973   1.826  -0.278  1.00  0.00           C  
HETATM   23  C20 UNL     1      -5.698   0.786  -1.015  1.00  0.00           C  
HETATM   24  O4  UNL     1      -6.727   1.113  -1.600  1.00  0.00           O  
HETATM   25  C21 UNL     1      -5.215  -0.599  -1.055  1.00  0.00           C  
HETATM   26  C22 UNL     1      -3.703  -0.582  -0.871  1.00  0.00           C  
HETATM   27  C23 UNL     1      -3.140   0.080  -2.090  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.810   0.758  -1.855  1.00  0.00           C  
HETATM   29  O5  UNL     1      -1.900   2.118  -1.640  1.00  0.00           O  
HETATM   30  H1  UNL     1       4.585  -2.205   1.628  1.00  0.00           H  
HETATM   31  H2  UNL     1       3.895  -0.987   2.726  1.00  0.00           H  
HETATM   32  H3  UNL     1       2.845  -2.275   1.934  1.00  0.00           H  
HETATM   33  H4  UNL     1       3.833  -1.262  -0.330  1.00  0.00           H  
HETATM   34  H5  UNL     1       4.576   0.822   1.712  1.00  0.00           H  
HETATM   35  H6  UNL     1       4.595   1.126  -0.062  1.00  0.00           H  
HETATM   36  H7  UNL     1       6.191  -0.934   1.613  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.268  -0.901  -0.195  1.00  0.00           H  
HETATM   38  H9  UNL     1       7.758   1.064  -1.128  1.00  0.00           H  
HETATM   39  H10 UNL     1       2.265   0.841   1.294  1.00  0.00           H  
HETATM   40  H11 UNL     1       2.533   1.977  -0.666  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.295   0.499  -1.489  1.00  0.00           H  
HETATM   42  H13 UNL     1       0.880   1.560  -2.202  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.328  -0.186  -2.311  1.00  0.00           H  
HETATM   44  H15 UNL     1       0.235   1.369   0.121  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.229  -1.092  -1.009  1.00  0.00           H  
HETATM   46  H17 UNL     1      -1.558   1.174   0.944  1.00  0.00           H  
HETATM   47  H18 UNL     1      -1.687  -0.919   2.455  1.00  0.00           H  
HETATM   48  H19 UNL     1      -1.325  -1.847   0.926  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.604  -1.504   2.296  1.00  0.00           H  
HETATM   50  H21 UNL     1       1.031   0.333   3.212  1.00  0.00           H  
HETATM   51  H22 UNL     1       2.088  -2.328  -0.492  1.00  0.00           H  
HETATM   52  H23 UNL     1       0.412  -2.626   0.201  1.00  0.00           H  
HETATM   53  H24 UNL     1       0.644  -1.857  -1.395  1.00  0.00           H  
HETATM   54  H25 UNL     1      -3.670  -0.481   2.534  1.00  0.00           H  
HETATM   55  H26 UNL     1      -4.889  -1.109   1.418  1.00  0.00           H  
HETATM   56  H27 UNL     1      -3.312  -1.917   1.422  1.00  0.00           H  
HETATM   57  H28 UNL     1      -4.505   1.340   1.734  1.00  0.00           H  
HETATM   58  H29 UNL     1      -3.217   2.156   0.854  1.00  0.00           H  
HETATM   59  H30 UNL     1      -4.510   2.594  -0.968  1.00  0.00           H  
HETATM   60  H31 UNL     1      -5.772   2.438   0.244  1.00  0.00           H  
HETATM   61  H32 UNL     1      -5.724  -1.314  -0.414  1.00  0.00           H  
HETATM   62  H33 UNL     1      -5.372  -0.970  -2.113  1.00  0.00           H  
HETATM   63  H34 UNL     1      -3.401  -1.665  -0.833  1.00  0.00           H  
HETATM   64  H35 UNL     1      -3.875   0.755  -2.598  1.00  0.00           H  
HETATM   65  H36 UNL     1      -2.945  -0.735  -2.838  1.00  0.00           H  
HETATM   66  H37 UNL     1      -1.175   0.654  -2.785  1.00  0.00           H  
HETATM   67  H38 UNL     1      -2.386   2.490  -2.418  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    8   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6    6    7
CONECT    7   38
CONECT    8    9   17   39
CONECT    9   10   40   41
CONECT   10   11   42   43
CONECT   11   12   17   44
CONECT   12   13   28   45
CONECT   13   14   19   46
CONECT   14   15   47   48
CONECT   15   16   17   49
CONECT   16   50
CONECT   17   18
CONECT   18   51   52   53
CONECT   19   20   21   26
CONECT   20   54   55   56
CONECT   21   22   57   58
CONECT   22   23   59   60
CONECT   23   24   24   25
CONECT   25   26   61   62
CONECT   26   27   63
CONECT   27   28   64   65
CONECT   28   29   66
CONECT   29   67
END

HMDB0000502
     RDKit          3D
3-Oxocholic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
    3.6846   -1.5693    1.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462   -0.6808    0.6023 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6953    0.3482    0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0419   -0.3075    0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0381    0.8173    0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0022    1.6609    1.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0438    0.9301   -0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3152    0.1094    0.4516 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4763    0.9069   -0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1770    0.6590   -1.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    0.4361   -0.5032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1106    0.0024   -0.7733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8515    0.1722    0.5620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2246   -0.8657    1.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -0.6408    1.6585 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5462    0.5080    2.3732 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0163   -0.5896    0.3488 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0534   -1.9038   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3241    0.0323    0.4260 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7783   -0.9401    1.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9896    1.3386    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9733    1.8259   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6976    0.7855   -1.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7265    1.1132   -1.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2147   -0.5994   -1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030   -0.5824   -0.8705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1396    0.0799   -2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104    0.7576   -1.8547 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8997    2.1175   -1.6402 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5853   -2.2051    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8955   -0.9869    2.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448   -2.2747    1.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8327   -1.2620   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5761    0.8215    1.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5949    1.1259   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1905   -0.9335    1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2678   -0.9009   -0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7580    1.0641   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    0.8408    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    1.9767   -0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2953    0.4993   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8803    1.5596   -2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3282   -0.1861   -2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2347    1.3689    0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2291   -1.0915   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5581    1.1740    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6874   -0.9190    2.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3245   -1.8469    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035   -1.5040    2.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0307    0.3328    3.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877   -2.3282   -0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.6259    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6436   -1.8566   -1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6695   -0.4805    2.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8891   -1.1086    1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3120   -1.9169    1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5052    1.3397    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175    2.1558    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5098    2.5943   -0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7718    2.4385    0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7244   -1.3145   -0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721   -0.9700   -2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4010   -1.6651   -0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749    0.7545   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9448   -0.7349   -2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750    0.6537   -2.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3864    2.4901   -2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  6
 13 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  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  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 25 61  1  0
 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
(5beta,7alpha,12alpha)-7,12-Dihydroxy-3-oxocholan-24-Oic acid	ChEBI
3-Dehydrocholic acid	ChEBI
3-Ketocholic acid	ChEBI
3-Oxocholic acid	ChEBI
7,12-Dihydroxy-3-oxocholanic acid	ChEBI
7alpha,12alpha-Dihydroxy-3-oxo-cholanoic acid	ChEBI
(5b,7a,12a)-7,12-Dihydroxy-3-oxocholan-24-Oate	Generator
(5b,7a,12a)-7,12-Dihydroxy-3-oxocholan-24-Oic acid	Generator
(5beta,7alpha,12alpha)-7,12-Dihydroxy-3-oxocholan-24-Oate	Generator
(5Β,7α,12α)-7,12-dihydroxy-3-oxocholan-24-Oate	Generator
(5Β,7α,12α)-7,12-dihydroxy-3-oxocholan-24-Oic acid	Generator
3-Dehydrocholate	Generator
3-Ketocholate	Generator
3-Oxocholate	Generator
7,12-Dihydroxy-3-oxocholanate	Generator
7a,12a-Dihydroxy-3-oxo-cholanoate	Generator
7a,12a-Dihydroxy-3-oxo-cholanoic acid	Generator
7alpha,12alpha-Dihydroxy-3-oxo-cholanoate	Generator
7Α,12α-dihydroxy-3-oxo-cholanoate	Generator
7Α,12α-dihydroxy-3-oxo-cholanoic acid	Generator
7a,12a-Dihydroxy-3-oxo-5b-cholan-24-Oate	Generator
7a,12a-Dihydroxy-3-oxo-5b-cholan-24-Oic acid	Generator
7alpha,12alpha-Dihydroxy-3-oxo-5beta-cholan-24-Oate	Generator
7Α,12α-dihydroxy-3-oxo-5β-cholan-24-Oate	Generator
7Α,12α-dihydroxy-3-oxo-5β-cholan-24-Oic acid	Generator
7alpha,12alpha-Dihydroxy-3-oxo-5beta-cholan-24-oic acid	HMDB

Chemical Formula

C₂₄H₃₈O₅

Average Molecular Weight

406.563

Monoisotopic Molecular Weight

406.271924324

IUPAC Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

2304-89-4

SMILES

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

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/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

InChI Key

OEKUSRBIIZNLHZ-DJDNIQJZSA-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-oxosteroid
12-hydroxysteroid
3-oxo-5-beta-steroid
7-hydroxysteroid
Hydroxysteroid
Oxosteroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010190 )

Ontology

Feces (PMID: 27275383)
Urine (PMID: 1112456)

Cellular substructure

Extracellular (HMDB: HMDB0000502)

Non-excretory biofluid

Biofluid or Excreta

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

Source

Exogenous

Exogenous (HMDB: HMDB0000502)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000502)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	218 - 220 °C	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	0.041 g/L	ALOGPS
logP	2.24	ALOGPS
logP	2.69	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.18	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.76 m³·mol⁻¹	ChemAxon
Polarizability	46.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	194.892	31661259
DarkChem	[M-H]-	186.875	31661259
AllCCS	[M+H]+	201.843	32859911
AllCCS	[M-H]-	201.139	32859911
DeepCCS	[M-2H]-	239.473	30932474
DeepCCS	[M+Na]+	213.489	30932474
AllCCS	[M+H]+	201.8	32859911
AllCCS	[M+H-H2O]+	199.7	32859911
AllCCS	[M+NH4]+	203.8	32859911
AllCCS	[M+Na]+	204.3	32859911
AllCCS	[M-H]-	201.1	32859911
AllCCS	[M+Na-2H]-	202.4	32859911
AllCCS	[M+HCOO]-	204.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.45 minutes	32390414
Predicted by Siyang on May 30, 2022	13.1445 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.88 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	70.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2751.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	193.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	555.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	589.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1013.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	508.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1517.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	434.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	256.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	243.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	92.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Oxocholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O	4130.7	Standard polar	33892256
3-Oxocholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O	3461.2	Standard non polar	33892256
3-Oxocholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O	3700.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Oxocholic acid,1TMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C	3390.6	Semi standard non polar	33892256
3-Oxocholic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O	3445.2	Semi standard non polar	33892256
3-Oxocholic acid,1TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O	3467.3	Semi standard non polar	33892256
3-Oxocholic acid,1TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O	3438.1	Semi standard non polar	33892256
3-Oxocholic acid,1TMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O	3399.3	Semi standard non polar	33892256
3-Oxocholic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C	3342.2	Semi standard non polar	33892256
3-Oxocholic acid,2TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C	3351.9	Semi standard non polar	33892256
3-Oxocholic acid,2TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C	3328.2	Semi standard non polar	33892256
3-Oxocholic acid,2TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3347.5	Semi standard non polar	33892256
3-Oxocholic acid,2TMS,isomer #5	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O	3404.5	Semi standard non polar	33892256
3-Oxocholic acid,2TMS,isomer #6	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O	3353.7	Semi standard non polar	33892256
3-Oxocholic acid,2TMS,isomer #7	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O	3370.7	Semi standard non polar	33892256
3-Oxocholic acid,2TMS,isomer #8	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O	3365.4	Semi standard non polar	33892256
3-Oxocholic acid,2TMS,isomer #9	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O	3398.5	Semi standard non polar	33892256
3-Oxocholic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C	3340.7	Semi standard non polar	33892256
3-Oxocholic acid,3TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C	3314.6	Semi standard non polar	33892256
3-Oxocholic acid,3TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3332.7	Semi standard non polar	33892256
3-Oxocholic acid,3TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C	3318.8	Semi standard non polar	33892256
3-Oxocholic acid,3TMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3336.4	Semi standard non polar	33892256
3-Oxocholic acid,3TMS,isomer #6	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O	3334.1	Semi standard non polar	33892256
3-Oxocholic acid,3TMS,isomer #7	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O	3350.1	Semi standard non polar	33892256
3-Oxocholic acid,4TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C	3313.6	Semi standard non polar	33892256
3-Oxocholic acid,4TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C	3363.7	Standard non polar	33892256
3-Oxocholic acid,4TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C	3502.5	Standard polar	33892256
3-Oxocholic acid,4TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3339.4	Semi standard non polar	33892256
3-Oxocholic acid,4TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3344.3	Standard non polar	33892256
3-Oxocholic acid,4TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3506.3	Standard polar	33892256
3-Oxocholic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3606.6	Semi standard non polar	33892256
3-Oxocholic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O	3665.5	Semi standard non polar	33892256
3-Oxocholic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O	3714.0	Semi standard non polar	33892256
3-Oxocholic acid,1TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3673.8	Semi standard non polar	33892256
3-Oxocholic acid,1TBDMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O	3629.9	Semi standard non polar	33892256
3-Oxocholic acid,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3789.9	Semi standard non polar	33892256
3-Oxocholic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3785.2	Semi standard non polar	33892256
3-Oxocholic acid,2TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3743.6	Semi standard non polar	33892256
3-Oxocholic acid,2TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3768.7	Semi standard non polar	33892256
3-Oxocholic acid,2TBDMS,isomer #5	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O	3867.5	Semi standard non polar	33892256
3-Oxocholic acid,2TBDMS,isomer #6	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O	3769.3	Semi standard non polar	33892256
3-Oxocholic acid,2TBDMS,isomer #7	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3804.8	Semi standard non polar	33892256
3-Oxocholic acid,2TBDMS,isomer #8	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O	3808.7	Semi standard non polar	33892256
3-Oxocholic acid,2TBDMS,isomer #9	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3850.5	Semi standard non polar	33892256
3-Oxocholic acid,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3993.8	Semi standard non polar	33892256
3-Oxocholic acid,3TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3923.3	Semi standard non polar	33892256
3-Oxocholic acid,3TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3946.1	Semi standard non polar	33892256
3-Oxocholic acid,3TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3937.7	Semi standard non polar	33892256
3-Oxocholic acid,3TBDMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3966.5	Semi standard non polar	33892256
3-Oxocholic acid,3TBDMS,isomer #6	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O	3952.2	Semi standard non polar	33892256
3-Oxocholic acid,3TBDMS,isomer #7	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3982.3	Semi standard non polar	33892256
3-Oxocholic acid,4TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4122.7	Semi standard non polar	33892256
3-Oxocholic acid,4TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4013.3	Standard non polar	33892256
3-Oxocholic acid,4TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3795.7	Standard polar	33892256
3-Oxocholic acid,4TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4144.8	Semi standard non polar	33892256
3-Oxocholic acid,4TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3932.6	Standard non polar	33892256
3-Oxocholic acid,4TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3799.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0449000000-a048d1efc6c00034ad57	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-2231189000-30c1ecbaf9541625b754	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic 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-Oxocholic 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-Oxocholic 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-Oxocholic 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-Oxocholic acid GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic 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-Oxocholic 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-Oxocholic 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-Oxocholic 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-Oxocholic 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-Oxocholic 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-Oxocholic acid GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic 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-Oxocholic 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-Oxocholic 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-Oxocholic acid GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxocholic 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-Oxocholic acid GC-MS (TBDMS_1_2) - 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-Oxocholic acid 10V, Positive-QTOF	splash10-0079-0009000000-64f2f2abc7d1633027d5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 20V, Positive-QTOF	splash10-00dr-0009000000-bcfa1c4097826adbabd9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 40V, Positive-QTOF	splash10-056u-2109000000-fe0a92a5f377efc3a7ae	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 10V, Negative-QTOF	splash10-0a4r-0008900000-dd8b045786455a7b2b5f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 20V, Negative-QTOF	splash10-052r-1009300000-40bda8fb29d7dc21b644	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-15440129ab1b7eb75b36	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 10V, Positive-QTOF	splash10-0ab9-0009600000-267c1c0d5a13c4bebc10	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 20V, Positive-QTOF	splash10-052r-2159000000-97af577c50737e77d152	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 40V, Positive-QTOF	splash10-0a4l-9232000000-99073abfe404b118814d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 10V, Negative-QTOF	splash10-0a4i-0000900000-f0b489debf71eabc30f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 20V, Negative-QTOF	splash10-0a4r-0008900000-e453fd1548d30dd5bb33	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxocholic acid 40V, Negative-QTOF	splash10-0udi-1029400000-c23a051d71ab55c9d40e	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Gall Bladder
Intestine
Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	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 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283956

PDB ID

Not Available

ChEBI ID

88108

Food Biomarker Ontology

Not Available

VMH ID

3DHCHOL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Production of 7a,12a-dihydroxy-3-keto-5b-cholanic acid. Jpn. Kokai Tokkyo Koho (1981), 12 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. [PubMed:10203155 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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-Oxocholic acid (HMDB0000502)

MOL for HMDB0000502 (3-Oxocholic acid)

3D MOL for HMDB0000502 (3-Oxocholic acid)

3D SDF for HMDB0000502 (3-Oxocholic acid)

3D-SDF for HMDB0000502 (3-Oxocholic acid)

PDB for HMDB0000502 (3-Oxocholic acid)

3D PDB for HMDB0000502 (3-Oxocholic acid)

SMILES for HMDB0000502 (3-Oxocholic acid)

INCHI for HMDB0000502 (3-Oxocholic acid)

Structure for HMDB0000502 (3-Oxocholic acid)

3D Structure for HMDB0000502 (3-Oxocholic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References