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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (21)transporters (13) Show 34 proteins XML

enzymes (21)transporters (13) Show 34 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:04 UTC

HMDB ID

HMDB0000619

Secondary Accession Numbers

HMDB00619

Metabolite Identification

Common Name

Cholic acid

Description

Cholic acid is a major primary bile acid produced in the liver and is usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH, and consequently require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). When present in sufficiently high levels, cholic acid can act as a hepatotoxin and a metabotoxin. A hepatotoxin causes damage to the liver or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (PMID: 1641875 ). The liver toxicity of bile acids appears to be due to their ability to peroxidate lipids and to lyse liver cells. Chronically high levels of cholic acid are associated with familial hypercholanemia. In hypercholanemia, bile acids, including cholic acid, are elevated in the blood. This disease causes liver damage, extensive itching, poor fat absorption, and can lead to rickets due to lack of calcium in bones. The deficiency of normal bile acids in the intestines results in a deficiency of vitamin K, which also adversely affects clotting of the blood. The bile acid ursodiol (ursodeoxycholic acid) can improve symptoms associated with familial hypercholanemia.

Structure

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


  Mrv1652307301920062D          

 29 32  0  0  1  0            999 V2000
    0.7294   -0.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987    0.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051   -0.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185    0.3176    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4661    2.1537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8100    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9249    0.9689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0297    1.7180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3737    1.2325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1221    2.6391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2812    0.3114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7223   -0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418    1.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1858    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7494    0.9421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6221    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903    3.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -0.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287   -0.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0332    0.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  9  8  1  0  0  0  0
 13  1  1  6  0  0  0
 13  4  1  0  0  0  0
 14 10  1  6  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16  5  1  1  0  0  0
 13 16  1  0  0  0  0
 17  6  1  1  0  0  0
 18 12  1  1  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21  7  1  0  0  0  0
 17 22  1  0  0  0  0
 22 18  1  6  0  0  0
 22 19  1  0  0  0  0
 23  2  1  1  0  0  0
 23  9  1  0  0  0  0
 23 14  1  0  0  0  0
 18 23  1  0  0  0  0
 24  3  1  1  0  0  0
 16 24  1  0  0  0  0
 24 17  1  0  0  0  0
 24 20  1  0  0  0  0
 15 25  1  6  0  0  0
 19 26  1  6  0  0  0
 20 27  1  6  0  0  0
 28 21  2  0  0  0  0
 29 21  1  0  0  0  0
M  END

HMDB0000619
     RDKit          3D
Cholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
    4.5608   -0.5811    2.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7007   -0.8609    0.8887 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4429   -1.5197   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6685   -0.8537   -0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4742    0.4649   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8643    1.5419   -0.6911 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394    0.6027   -2.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561    0.1000    0.7877 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8255    1.5549    0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    2.0902    0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405    0.8821    0.5220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7843    0.9834   -0.1250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3923   -0.4233   -0.0019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4971   -1.4084   -0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8664   -1.4865   -0.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8222   -2.0168    1.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4883   -0.1325   -0.1502 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7459    0.2684   -1.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8037   -0.4845   -0.4151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0110   -1.3687   -1.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6249   -1.0972    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9925   -1.3486    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6828   -0.1276   -0.3559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3954    0.4452    0.7013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8318    0.8703   -1.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843    0.8708   -0.7136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0819    1.7942    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148    1.9431    0.7196 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4139    1.6813    2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8234   -0.2812    2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589   -1.4861    2.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2186    0.2853    1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1124   -1.8189    1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8408   -1.8275   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313   -2.5587    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1142   -1.4895   -1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5099   -0.8783    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0198    1.4106   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0895    0.0175    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450    1.9923   -0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995    1.9493    1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2499    2.8117   -0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1539    2.6247    1.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3820    0.4905    1.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8131    1.3352   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2921   -0.6486    1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509   -1.2444   -1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9537   -2.4213   -0.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732   -2.1810   -0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3650   -1.5088    1.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    1.1923   -1.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    0.4443   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008   -0.5685   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2699   -1.1316   -2.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701   -2.4341   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0083   -1.1462   -2.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1588   -2.0673    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6088   -0.4931    1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308   -2.1699   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5973   -1.7827    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4756   -0.5048   -1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4109   -0.1009    1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2269    1.9019   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457    0.7916   -2.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8032    1.2787   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    2.8111    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6765    1.5491    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    2.9606    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295    2.5125    2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  6
 13 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  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  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  6
 24 62  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  6
 27 66  1  0
 27 67  1  0
 28 68  1  1
 29 69  1  0
M  END


  Mrv1652307301920062D          

 29 32  0  0  1  0            999 V2000
    0.7294   -0.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987    0.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051   -0.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185    0.3176    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4661    2.1537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8100    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9249    0.9689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0297    1.7180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3737    1.2325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1221    2.6391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2812    0.3114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7223   -0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418    1.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1858    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7494    0.9421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6221    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903    3.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -0.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287   -0.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0332    0.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  9  8  1  0  0  0  0
 13  1  1  6  0  0  0
 13  4  1  0  0  0  0
 14 10  1  6  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16  5  1  1  0  0  0
 13 16  1  0  0  0  0
 17  6  1  1  0  0  0
 18 12  1  1  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21  7  1  0  0  0  0
 17 22  1  0  0  0  0
 22 18  1  6  0  0  0
 22 19  1  0  0  0  0
 23  2  1  1  0  0  0
 23  9  1  0  0  0  0
 23 14  1  0  0  0  0
 18 23  1  0  0  0  0
 24  3  1  1  0  0  0
 16 24  1  0  0  0  0
 24 17  1  0  0  0  0
 24 20  1  0  0  0  0
 15 25  1  6  0  0  0
 19 26  1  6  0  0  0
 20 27  1  6  0  0  0
 28 21  2  0  0  0  0
 29 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000619

> <DATABASE_NAME>
hmdb

> <SMILES>
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@H](O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O5/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/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

> <INCHI_KEY>
BHQCQFFYRZLCQQ-OELDTZBJSA-N

> <FORMULA>
C24H40O5

> <MOLECULAR_WEIGHT>
408.5714

> <EXACT_MASS>
408.28757439

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
47.050943062586015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.482494456666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475012423758966

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15944265438213734

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
110.78929999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000619
     RDKit          3D
Cholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
    4.5608   -0.5811    2.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7007   -0.8609    0.8887 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4429   -1.5197   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6685   -0.8537   -0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4742    0.4649   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8643    1.5419   -0.6911 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394    0.6027   -2.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561    0.1000    0.7877 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8255    1.5549    0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    2.0902    0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405    0.8821    0.5220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7843    0.9834   -0.1250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3923   -0.4233   -0.0019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4971   -1.4084   -0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8664   -1.4865   -0.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8222   -2.0168    1.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4883   -0.1325   -0.1502 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7459    0.2684   -1.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8037   -0.4845   -0.4151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0110   -1.3687   -1.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6249   -1.0972    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9925   -1.3486    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6828   -0.1276   -0.3559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3954    0.4452    0.7013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8318    0.8703   -1.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843    0.8708   -0.7136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0819    1.7942    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148    1.9431    0.7196 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4139    1.6813    2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8234   -0.2812    2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589   -1.4861    2.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2186    0.2853    1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1124   -1.8189    1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8408   -1.8275   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313   -2.5587    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1142   -1.4895   -1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5099   -0.8783    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0198    1.4106   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0895    0.0175    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450    1.9923   -0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995    1.9493    1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2499    2.8117   -0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1539    2.6247    1.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3820    0.4905    1.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8131    1.3352   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2921   -0.6486    1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509   -1.2444   -1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9537   -2.4213   -0.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732   -2.1810   -0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3650   -1.5088    1.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    1.1923   -1.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    0.4443   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008   -0.5685   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2699   -1.1316   -2.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701   -2.4341   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0083   -1.1462   -2.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1588   -2.0673    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6088   -0.4931    1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308   -2.1699   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5973   -1.7827    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4756   -0.5048   -1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4109   -0.1009    1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2269    1.9019   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457    0.7916   -2.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8032    1.2787   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    2.8111    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6765    1.5491    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    2.9606    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295    2.5125    2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  6
 13 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  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  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  6
 24 62  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  6
 27 66  1  0
 27 67  1  0
 28 68  1  1
 29 69  1  0
M  END

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       1.362  -0.834   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.290   1.123   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.594   0.373   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.744   0.803   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.298   3.288   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.573   4.152   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.690  -0.412   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.322   1.665   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.806   1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.853   4.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.344   5.198   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.774   0.852   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.781   0.593   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.337   4.020   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.845   3.114   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.726   1.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.789   3.207   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.298   2.301   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.828   4.926   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.258   0.581   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.215  -0.202   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.305   3.478   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.813   2.572   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.266   1.759   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.361   3.385   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.835   6.104   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.735  -0.867   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.160  -1.418   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -3.795   1.225   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    7   13                                                       
CONECT    5    6   16                                                       
CONECT    6    5   17                                                       
CONECT    7    4   21                                                       
CONECT    8    9   15                                                       
CONECT    9    8   23                                                       
CONECT   10   14   15                                                       
CONECT   11   14   19                                                       
CONECT   12   18   20                                                       
CONECT   13    1    4   16                                                  
CONECT   14   10   11   23                                                  
CONECT   15    8   10   25                                                  
CONECT   16    5   13   24                                                  
CONECT   17    6   22   24                                                  
CONECT   18   12   22   23                                                  
CONECT   19   11   22   26                                                  
CONECT   20   12   24   27                                                  
CONECT   21    7   28   29                                                  
CONECT   22   17   18   19                                                  
CONECT   23    2    9   14   18                                             
CONECT   24    3   16   17   20                                             
CONECT   25   15                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   21                                                            
CONECT   29   21                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0000619
HETATM    1  C1  UNL     1       4.561  -0.581   2.143  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.701  -0.861   0.889  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.443  -1.520  -0.173  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.669  -0.854  -0.691  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.474   0.465  -1.262  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.864   1.542  -0.691  1.00  0.00           O  
HETATM    7  O2  UNL     1       4.839   0.603  -2.485  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.656   0.100   0.788  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.826   1.555   0.667  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.373   2.090   0.585  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.541   0.882   0.522  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.784   0.983  -0.125  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.392  -0.423  -0.002  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.497  -1.408  -0.699  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.866  -1.486  -0.043  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.822  -2.017   1.217  1.00  0.00           O  
HETATM   17  C14 UNL     1       1.488  -0.133  -0.150  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.746   0.268  -1.555  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.804  -0.484  -0.415  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.011  -1.369  -1.648  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.625  -1.097   0.696  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.992  -1.349   0.170  1.00  0.00           C  
HETATM   23  C20 UNL     1      -5.683  -0.128  -0.356  1.00  0.00           C  
HETATM   24  O4  UNL     1      -6.395   0.445   0.701  1.00  0.00           O  
HETATM   25  C21 UNL     1      -4.832   0.870  -1.023  1.00  0.00           C  
HETATM   26  C22 UNL     1      -3.384   0.871  -0.714  1.00  0.00           C  
HETATM   27  C23 UNL     1      -3.082   1.794   0.450  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.615   1.943   0.720  1.00  0.00           C  
HETATM   29  O5  UNL     1      -1.414   1.681   2.078  1.00  0.00           O  
HETATM   30  H1  UNL     1       3.823  -0.281   2.918  1.00  0.00           H  
HETATM   31  H2  UNL     1       5.059  -1.486   2.496  1.00  0.00           H  
HETATM   32  H3  UNL     1       5.219   0.285   1.979  1.00  0.00           H  
HETATM   33  H4  UNL     1       3.112  -1.819   1.359  1.00  0.00           H  
HETATM   34  H5  UNL     1       3.841  -1.827  -1.062  1.00  0.00           H  
HETATM   35  H6  UNL     1       4.831  -2.559   0.173  1.00  0.00           H  
HETATM   36  H7  UNL     1       6.114  -1.489  -1.533  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.510  -0.878   0.061  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.020   1.411  -3.089  1.00  0.00           H  
HETATM   39  H10 UNL     1       2.090   0.018   1.834  1.00  0.00           H  
HETATM   40  H11 UNL     1       3.345   1.992  -0.158  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.300   1.949   1.608  1.00  0.00           H  
HETATM   42  H13 UNL     1       1.250   2.812  -0.218  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.154   2.625   1.548  1.00  0.00           H  
HETATM   44  H15 UNL     1       0.382   0.491   1.554  1.00  0.00           H  
HETATM   45  H16 UNL     1      -0.813   1.335  -1.158  1.00  0.00           H  
HETATM   46  H17 UNL     1      -1.292  -0.649   1.102  1.00  0.00           H  
HETATM   47  H18 UNL     1      -0.351  -1.244  -1.764  1.00  0.00           H  
HETATM   48  H19 UNL     1      -0.954  -2.421  -0.569  1.00  0.00           H  
HETATM   49  H20 UNL     1       1.473  -2.181  -0.674  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.365  -1.509   1.906  1.00  0.00           H  
HETATM   51  H22 UNL     1       2.311   1.192  -1.640  1.00  0.00           H  
HETATM   52  H23 UNL     1       0.745   0.444  -2.035  1.00  0.00           H  
HETATM   53  H24 UNL     1       2.201  -0.569  -2.119  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.270  -1.132  -2.440  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.970  -2.434  -1.343  1.00  0.00           H  
HETATM   56  H27 UNL     1      -4.008  -1.146  -2.102  1.00  0.00           H  
HETATM   57  H28 UNL     1      -3.159  -2.067   0.942  1.00  0.00           H  
HETATM   58  H29 UNL     1      -3.609  -0.493   1.619  1.00  0.00           H  
HETATM   59  H30 UNL     1      -4.931  -2.170  -0.576  1.00  0.00           H  
HETATM   60  H31 UNL     1      -5.597  -1.783   1.021  1.00  0.00           H  
HETATM   61  H32 UNL     1      -6.476  -0.505  -1.064  1.00  0.00           H  
HETATM   62  H33 UNL     1      -6.411  -0.101   1.508  1.00  0.00           H  
HETATM   63  H34 UNL     1      -5.227   1.902  -0.790  1.00  0.00           H  
HETATM   64  H35 UNL     1      -4.946   0.792  -2.139  1.00  0.00           H  
HETATM   65  H36 UNL     1      -2.803   1.279  -1.577  1.00  0.00           H  
HETATM   66  H37 UNL     1      -3.452   2.811   0.125  1.00  0.00           H  
HETATM   67  H38 UNL     1      -3.677   1.549   1.349  1.00  0.00           H  
HETATM   68  H39 UNL     1      -1.228   2.961   0.509  1.00  0.00           H  
HETATM   69  H40 UNL     1      -1.330   2.513   2.615  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   25   61
CONECT   24   62
CONECT   25   26   63   64
CONECT   26   27   65
CONECT   27   28   66   67
CONECT   28   29   68
CONECT   29   69
END

HMDB0000619
     RDKit          3D
Cholic acid
 69 72  0  0  0  0  0  0  0  0999 V2000
    4.5608   -0.5811    2.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7007   -0.8609    0.8887 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4429   -1.5197   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6685   -0.8537   -0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4742    0.4649   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8643    1.5419   -0.6911 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394    0.6027   -2.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561    0.1000    0.7877 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8255    1.5549    0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    2.0902    0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405    0.8821    0.5220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7843    0.9834   -0.1250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3923   -0.4233   -0.0019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4971   -1.4084   -0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8664   -1.4865   -0.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8222   -2.0168    1.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4883   -0.1325   -0.1502 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7459    0.2684   -1.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8037   -0.4845   -0.4151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0110   -1.3687   -1.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6249   -1.0972    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9925   -1.3486    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6828   -0.1276   -0.3559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3954    0.4452    0.7013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8318    0.8703   -1.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843    0.8708   -0.7136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0819    1.7942    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148    1.9431    0.7196 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4139    1.6813    2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8234   -0.2812    2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589   -1.4861    2.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2186    0.2853    1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1124   -1.8189    1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8408   -1.8275   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313   -2.5587    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1142   -1.4895   -1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5099   -0.8783    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0198    1.4106   -3.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0895    0.0175    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450    1.9923   -0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995    1.9493    1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2499    2.8117   -0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1539    2.6247    1.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3820    0.4905    1.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8131    1.3352   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2921   -0.6486    1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509   -1.2444   -1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9537   -2.4213   -0.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732   -2.1810   -0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3650   -1.5088    1.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    1.1923   -1.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    0.4443   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008   -0.5685   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2699   -1.1316   -2.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701   -2.4341   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0083   -1.1462   -2.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1588   -2.0673    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6088   -0.4931    1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308   -2.1699   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5973   -1.7827    1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4756   -0.5048   -1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4109   -0.1009    1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2269    1.9019   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457    0.7916   -2.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8032    1.2787   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    2.8111    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6765    1.5491    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    2.9606    0.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295    2.5125    2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  6
 13 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  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  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  6
 24 62  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  6
 27 66  1  0
 27 67  1  0
 28 68  1  1
 29 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid	ChEBI
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate	ChEBI
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid	ChEBI
Cholsaeure	ChEBI
Cholate	Kegg
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oate	Generator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid	Generator
3a,7a,12a-Trihydroxy-5b-cholanate	Generator
3a,7a,12a-Trihydroxy-5b-cholanic acid	Generator
3Α,7α,12α-trihydroxy-5β-cholanate	Generator
3Α,7α,12α-trihydroxy-5β-cholanic acid	Generator
Allocholate	HMDB
17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triol	HMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-Oate	HMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-Oic acid	HMDB
3a,7a,12a-Trihydroxy-5b-cholanoate	HMDB
3a,7a,12a-Trihydroxy-5b-cholanoic acid	HMDB
3a,7a,12a-Trihydroxy-b-cholanate	HMDB
3a,7a,12a-Trihydroxy-b-cholanic acid	HMDB
3a,7a,12a-Trihydroxy-beta-cholanate	HMDB
3a,7a,12a-Trihydroxy-beta-cholanic acid	HMDB
3a,7a,12a-Trihydroxycholanate	HMDB
3a,7a,12a-Trihydroxycholanic acid	HMDB
5b-Cholanic acid-3a,7a,12a-triol	HMDB
5b-Cholate	HMDB
5b-Cholic acid	HMDB
Cholalate	HMDB
Cholalic acid	HMDB
Cholalin	HMDB
Colalin	HMDB
Acid, cholic	HMDB
Cholic acid	Generator

Chemical Formula

C₂₄H₄₀O₅

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

IUPAC Name

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

Traditional Name

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

CAS Registry Number

81-25-4

SMILES

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@H](O)[C@]12C

InChI Identifier

InChI=1S/C24H40O5/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/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

InChI Key

BHQCQFFYRZLCQQ-OELDTZBJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl 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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Trihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:16359 )
trihydroxy-5beta-cholanic acid (CHEBI:16359 )
C24 bile acids, alcohols, and derivatives (C00695 )
Cholane and derivatives (C00695 )
C24 bile acids, alcohols, and derivatives (LMST04010001 )

Ontology

Physiological effect

Organoleptic effect

Odor

bitter

Platelet (HMDB: HMDB0000619)

Biofluid or Excreta

Non-excretory biofluid

Bile (PMID: 16548228)
Blood (PMID: 15185309)

Excreta

Urine (PMID: 2621422)
Feces (PMID: 22664055)

Cellular substructure

Extracellular (HMDB: HMDB0000619)
Membrane (HMDB: HMDB0000619)

Cellular element

Platelet (HMDB: HMDB0000619)

Tissue substructure

Placenta (HMDB: HMDB0000619)

Source

Exogenous

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Zellweger Syndrome (PathBank: SMP0120715)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0000314)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0000318)
Familial Hypercholanemia (FHCA) (PathBank: SMP0000317)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0000315)
27-Hydroxylase Deficiency (PathBank: SMP0000720)

Metabolic pathway

Bile Acid Biosynthesis (HMDB: HMDB0000619)

Role

Biological role

metabolite (HMDB: HMDB0000619)

Industrial application

Pharmaceutical industry

Biomarker

Cystic fibrosis (MarkerDB: MDB00000202)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	197 - 201 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.18 mg/mL	Not Available
LogP	2.02	RODA,A ET AL. (1990)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	204.627	30932474
[M-H]-	MetCCS_train_neg	200.724	30932474
[M-H]-	Not Available	202.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000201

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.074 g/L	ALOGPS
logP	2.48	ChemAxon
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.79 m³·mol⁻¹	ChemAxon
Polarizability	47.05 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]+	193.16	31661259
DarkChem	[M-H]-	192.539	31661259
AllCCS	[M+H]+	203.044	32859911
AllCCS	[M-H]-	200.947	32859911
DeepCCS	[M-2H]-	231.769	30932474
DeepCCS	[M+Na]+	205.889	30932474
AllCCS	[M+H]+	203.0	32859911
AllCCS	[M+H-H2O]+	201.0	32859911
AllCCS	[M+NH4]+	204.9	32859911
AllCCS	[M+Na]+	205.4	32859911
AllCCS	[M-H]-	200.9	32859911
AllCCS	[M+Na-2H]-	202.4	32859911
AllCCS	[M+HCOO]-	204.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cholic acid	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@H](O)[C@]12C	4216.7	Standard polar	33892256
Cholic acid	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@H](O)[C@]12C	3464.1	Standard non polar	33892256
Cholic acid	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@H](O)[C@]12C	3681.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cholic acid,1TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3395.4	Semi standard non polar	33892256
Cholic 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)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3367.0	Semi standard non polar	33892256
Cholic acid,1TMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3442.5	Semi standard non polar	33892256
Cholic 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[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3422.2	Semi standard non polar	33892256
Cholic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3379.4	Semi standard non polar	33892256
Cholic acid,2TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3385.4	Semi standard non polar	33892256
Cholic acid,2TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3314.0	Semi standard non polar	33892256
Cholic acid,2TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3337.1	Semi standard non polar	33892256
Cholic acid,2TMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3336.2	Semi standard non polar	33892256
Cholic 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)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3372.3	Semi standard non polar	33892256
Cholic 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)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3343.2	Semi standard non polar	33892256
Cholic acid,3TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3329.1	Semi standard non polar	33892256
Cholic 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@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3321.6	Semi standard non polar	33892256
Cholic acid,3TMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3336.5	Semi standard non polar	33892256
Cholic acid,4TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3341.1	Semi standard non polar	33892256
Cholic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3642.8	Semi standard non polar	33892256
Cholic 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)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3579.0	Semi standard non polar	33892256
Cholic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3656.8	Semi standard non polar	33892256
Cholic 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[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3636.4	Semi standard non polar	33892256
Cholic acid,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3838.8	Semi standard non polar	33892256
Cholic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3849.5	Semi standard non polar	33892256
Cholic acid,2TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3753.0	Semi standard non polar	33892256
Cholic acid,2TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3767.2	Semi standard non polar	33892256
Cholic acid,2TBDMS,isomer #5	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[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	3761.4	Semi standard non polar	33892256
Cholic 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)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3798.6	Semi standard non polar	33892256
Cholic 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)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3986.6	Semi standard non polar	33892256
Cholic acid,3TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3958.5	Semi standard non polar	33892256
Cholic 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@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3941.8	Semi standard non polar	33892256
Cholic acid,3TBDMS,isomer #4	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3967.2	Semi standard non polar	33892256
Cholic acid,4TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4162.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Cholic acid EI-B (Non-derivatized)	splash10-0fk9-5796000000-2876080f3fa17fb96370	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cholic acid EI-B (Non-derivatized)	splash10-0fk9-5796000000-2876080f3fa17fb96370	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-0439000000-4e43231560df6c61b96d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (4 TMS) - 70eV, Positive	splash10-001i-1100049000-86faaffe1dc0eadf9e75	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0596-9642000000-e425981b8a0ac72ea6ee	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-0000900000-806d3b03c76019afbf7d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-0000900000-4edb603ca5534669120e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-0000900000-4a76e64b2f0411d0b701	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-0001900000-41aa3a7cb25fcf549046	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-0057900000-790a3808fa512d5d1687	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-0010900000-e6bedfc253363160a37e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-0030900000-da4a7bfccbaf1e42171c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-0020900000-772055897702843a1d50	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-0021900000-0405fe63d70d3a88bf6f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QQ , negative-QTOF	splash10-0aou-3844900000-cb3c2aba1b9a29785616	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-IT , negative-QTOF	splash10-0007-0019000000-fb9a5b5952cf65eb7988	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QTOF , negative-QTOF	splash10-0a4i-0001900000-9583bd9c6c0d2b069b68	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-QTOF , negative-QTOF	splash10-0a4i-1027900000-31f3cf065ad48561c0a2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0000900000-b0504ee652d51a711f3a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0000900000-18dd8b6be45775ec83c2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-ITFT , negative-QTOF	splash10-0007-0019000000-285d3d0d87f5471b419a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-ITFT , negative-QTOF	splash10-0007-0019000000-0fcb0f6819b05ab63c12	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0000900000-b0504ee652d51a711f3a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cholic acid LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0000900000-18dd8b6be45775ec83c2	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholic acid 10V, Positive-QTOF	splash10-00dl-0009000000-85abf6e916e1cc1c46b6	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholic acid 20V, Positive-QTOF	splash10-00dl-0009000000-476dc71e401cc2327292	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholic acid 40V, Positive-QTOF	splash10-00nb-2109000000-0181c85f78bb9e29ea53	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholic acid 10V, Negative-QTOF	splash10-0a4r-0009700000-63a8d2c748b3bc631c17	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholic acid 20V, Negative-QTOF	splash10-052r-1009200000-ba378537551be8134141	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cholic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-caef890bd53da215442e	2015-09-15	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Urine

Tissue Locations

Intestine
Kidney
Liver
Placenta
Platelet
Spleen

Pathways

Name	SMPDB/PathBank	KEGG
Primary bile acid biosynthesis	Not Available
Congenital Bile Acid Synthesis Defect Type II		Not Available
Congenital Bile Acid Synthesis Defect Type III		Not Available
Familial Hypercholanemia (FHCA)		Not Available
Zellweger Syndrome		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bile	Detected and Quantified	32060 (31830-32280) uM	Adult (>18 years old)	Both	Normal	16548228	details
Blood	Detected and Quantified	1.7 +/- 0.3 uM	Newborn (0-30 days old)	Both	Normal	16553252	details
Blood	Detected and Quantified	0.1(0-0.1) uM	Infant (0-1 year old)	Both	Normal	27163928	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.72 +/- 0.24 uM	Adult (>18 years old)	Both	Normal	15185309	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	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
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected and Quantified	44.71 +/- 47.79 nmol/g dry feces	Not Specified	Not Specified	Normal	22664055	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	18085514	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	48.5 (2.8-124.5) uM	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Blood	Detected and Quantified	13.8 (1.2-36.5) uM	Adult (>18 years old)	Both	Primary biliary cirrhosis	2621422	details
Blood	Detected and Quantified	15.6 +/- 3.6 uM	Newborn (0-30 days old)	Both	Extrahepatic biliary atresia (EHBA)	16553252	details
Blood	Detected and Quantified	0.3 +/- 0.2 uM	Infant (0-1 year old)	Both	GI disorder	28521607	details
Blood	Detected and Quantified	0.4 +/- 0.4 uM	Infant (0-1 year old)	Both	GI disorder	28521607	details
Blood	Detected and Quantified	0.7 +/- 0.4 uM	Infant (0-1 year old)	Both	GI disorder	28521607	details
Blood	Detected and Quantified	1.4 +/- 0.9 uM	Infant (0-1 year old)	Both	GI disorder	28521607	details
Blood	Detected and Quantified	0.1(0.1-0.2) uM	Infant (0-1 year old)	Both	Severe acute malnutrition	27163928	details
Blood	Detected and Quantified	1.71 +/- 0.29 uM	Adult (>18 years old)	Both	Cystic fibrosis	15185309	details
Blood	Detected and Quantified	1.52 +/- 0.26 uM	Children (1-13 years old)	Both	Cystic fibrosis	15185309	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Recurrent Clostridium difficile infection	24284963	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Recurrent Clostridium difficile infection	24284963	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	24284963	details
Urine	Detected and Quantified	2.2 (0.13-6.6) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	1.9 (0.11-7.2) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	1.969 +/- 0.612 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.075 +/- 0.090 umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	3944741	details

Associated Disorders and Diseases

Disease References

Cystic fibrosis
Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
Biliary atresia
Gustafsson J, Alvelius G, Bjorkhem I, Nemeth A: Bile acid metabolism in extrahepatic biliary atresia: lithocholic acid in stored dried blood collected at neonatal screening. Ups J Med Sci. 2006;111(1):131-6. [PubMed:16553252 ] Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. [PubMed:3944741 ]
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 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Cirrhosis
Batta AK, Arora R, Salen G, Tint GS, Eskreis D, Katz S: Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment. J Lipid Res. 1989 Dec;30(12):1953-62. [PubMed:2621422 ]
Primary biliary cirrhosis
Batta AK, Arora R, Salen G, Tint GS, Eskreis D, Katz S: Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment. J Lipid Res. 1989 Dec;30(12):1953-62. [PubMed:2621422 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

219700 (Cystic fibrosis)
210500 (Biliary atresia)
114500 (Colorectal cancer)
266600 (Crohn's disease)
109720 (Primary biliary cirrhosis)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB02659

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012810

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16359

Food Biomarker Ontology

Not Available

VMH ID

CHOLATE

MarkerDB ID

MDB00000202

Good Scents ID

Not Available

References

Synthesis Reference

Calimente, Daniel. Synthesis and characterization of new naphthalimide and cholic acid-containing complexing agents. (1998), 104 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10. [PubMed:16548228 ]
Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
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 ]
Wildgrube HJ, Stang H, Winkler M, Mauritz G: [Value of serum levels of conjugated cholic acid in the diagnosis of liver disease (author's transl)]. Dtsch Med Wochenschr. 1982 Aug 20;107(33):1235-7. [PubMed:7106004 ]
Rodrigues CM, Marin JJ, Brites D: Bile acid patterns in meconium are influenced by cholestasis of pregnancy and not altered by ursodeoxycholic acid treatment. Gut. 1999 Sep;45(3):446-52. [PubMed:10446117 ]
Einarsson K, Reihner E, Ewerth S, Bjorkhem I: Serum concentrations of unconjugated and conjugated cholic acid in portal venous and systemic venous blood of fasting man. Scand J Clin Lab Invest. 1989 Feb;49(1):83-91. [PubMed:2727621 ]
Briz O, Macias RI, Serrano MA, Gonzalez-Gallego J, Bayon JE, Marin JJ: Excretion of foetal bilirubin by the rat placenta-maternal liver tandem. Placenta. 2003 May;24(5):462-72. [PubMed:12744922 ]
Gustafsson J, Alvelius G, Bjorkhem I, Nemeth A: Bile acid metabolism in extrahepatic biliary atresia: lithocholic acid in stored dried blood collected at neonatal screening. Ups J Med Sci. 2006;111(1):131-6. [PubMed:16553252 ]
Salen G, Shefer S, Tint GS, Nicolau G, Dayal B, Batta AK: Biosynthesis of bile acids in cerebrotendinous xanthomatosis. Relationship of bile acid pool sizes and synthesis rates to hydroxylations at C-12, C-25, and C-26. J Clin Invest. 1985 Aug;76(2):744-51. [PubMed:4031069 ]
Brites D, Poeiras J, Rodrigues C: [Intrahepatic cholestasis in pregnancy. Its etiopathogenesis, prognosis and therapy]. Acta Med Port. 1994 Mar;7(3):181-8. [PubMed:8209706 ]
Van Den Berg JW, Van Blankenstein M, Bosman-Jacobs EP, Frenkel M, Horchner P, Ooost-Harwig OI, Wilson JH: Solid phase radioimmunoassay for determination of conjugated cholic acid in serum. Clin Chim Acta. 1976 Dec 1;73(2):277-83. [PubMed:1000848 ]
Pomare EW, Low-Beer TS: Proceedings: Effect of administration of a colonic metabolite of cholic acid on cholesterol levels in bile and blood. Gut. 1974 Oct;15(10):830. [PubMed:4434946 ]
Einarsson K, Bergstrom M, Eklof R, Nord CE, Bjorkhem I: Comparison of the proportion of unconjugated to total serum cholic acid and the [14C]-xylose breath test in patients with suspected small intestinal bacterial overgrowth. Scand J Clin Lab Invest. 1992 Sep;52(5):425-30. [PubMed:1514020 ]
Ewerth S, Bjorkhem I, Einarsson K, Ost L: Lymphatic transport of bile acids in man. J Lipid Res. 1982 Nov;23(8):1183-6. [PubMed:7175375 ]
LaRusso NF, Hoffman NE, Hofmann AF, Korman MG: Validity and sensitivity of an intravenous bile acid tolerance test in patients with liver disease. N Engl J Med. 1975 Jun 5;292(23):1209-14. [PubMed:1128572 ]
Lillienau J, Schteingart CD, Hofmann AF: Physicochemical and physiological properties of cholylsarcosine. A potential replacement detergent for bile acid deficiency states in the small intestine. J Clin Invest. 1992 Feb;89(2):420-31. [PubMed:1371123 ]
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 ]
Delzenne NM, Calderon PB, Taper HS, Roberfroid MB: Comparative hepatotoxicity of cholic acid, deoxycholic acid and lithocholic acid in the rat: in vivo and in vitro studies. Toxicol Lett. 1992 Jul;61(2-3):291-304. [PubMed:1641875 ]

Only showing the first 10 proteins. There are 34 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G1B
Uniprot ID:: P04054
Molecular weight:: 16359.535

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

3. Alcohol dehydrogenase 1C

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1C
Uniprot ID:: P00326
Molecular weight:: 39867.27

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

4. Acyl-coenzyme A thioesterase 8

General function:: Involved in acyl-CoA thioesterase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:: ACOT8
Uniprot ID:: O14734
Molecular weight:: 35914.02

Reactions

Choloyl-CoA + Water → Cholic acid + Coenzyme A	details

Enzyme Details

5. Ferrochelatase, mitochondrial

General function:: Involved in ferrochelatase activity
Specific function:: Catalyzes the ferrous insertion into protoporphyrin IX.
Gene Name:: FECH
Uniprot ID:: P22830
Molecular weight:: 47861.77

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

6. Cytochrome c oxidase subunit 1

General function:: Involved in iron ion binding
Specific function:: Cytochrome c oxidase is the component of the respiratory chain that catalyzes the reduction of oxygen to water. Subunits 1-3 form the functional core of the enzyme complex. CO I is the catalytic subunit of the enzyme. Electrons originating in cytochrome c are transferred via the copper A center of subunit 2 and heme A of subunit 1 to the bimetallic center formed by heme A3 and copper B.
Gene Name:: MT-CO1
Uniprot ID:: P00395
Molecular weight:: 57040.91

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

7. Cytochrome c oxidase subunit 7A1, mitochondrial

General function:: Involved in cytochrome-c oxidase activity
Specific function:: This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport
Gene Name:: COX7A1
Uniprot ID:: P24310
Molecular weight:: 9117.4

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

8. Bile acyl-CoA synthetase

General function:: Involved in catalytic activity
Specific function:: Acyl-CoA synthetase involved in bile acid metabolism. Proposed to catalyze the first step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi by activating them to their CoA thioesters. Seems to activate secondary bile acids entering the liver from the enterohepatic circulation. In vitro, also activates 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanate (THCA), the C27 precursor of cholic acid deriving from the de novo synthesis from cholesterol.
Gene Name:: SLC27A5
Uniprot ID:: Q9Y2P5
Molecular weight:: 75384.375

Reactions

Adenosine triphosphate + Cholic acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Choloyl-CoA	details

Enzyme Details

9. Cytochrome c oxidase subunit 5A, mitochondrial

General function:: Involved in cytochrome-c oxidase activity
Specific function:: This is the heme A-containing chain of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport
Gene Name:: COX5A
Uniprot ID:: P20674
Molecular weight:: 16762.0

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

10. Cytochrome c oxidase subunit 6A2, mitochondrial

General function:: Involved in cytochrome-c oxidase activity
Specific function:: This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport
Gene Name:: COX6A2
Uniprot ID:: Q02221
Molecular weight:: 10815.3

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

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

References

Cui Y, Konig J, Leier I, Buchholz U, Keppler D: Hepatic uptake of bilirubin and its conjugates by the human organic anion transporter SLC21A6. J Biol Chem. 2001 Mar 30;276(13):9626-30. Epub 2000 Dec 27. [PubMed:11134001 ]

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 ]
Hartmann G, Cheung AK, Piquette-Miller M: Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia. J Pharmacol Exp Ther. 2002 Oct;303(1):273-81. [PubMed:12235261 ]
Konig J, Cui Y, Nies AT, Keppler D: A novel human organic anion transporting polypeptide localized to the basolateral hepatocyte membrane. Am J Physiol Gastrointest Liver Physiol. 2000 Jan;278(1):G156-64. [PubMed:10644574 ]
Cui Y, Konig J, Leier I, Buchholz U, Keppler D: Hepatic uptake of bilirubin and its conjugates by the human organic anion transporter SLC21A6. J Biol Chem. 2001 Mar 30;276(13):9626-30. Epub 2000 Dec 27. [PubMed:11134001 ]

Enzyme Details

3. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [PubMed:11438506 ]

Enzyme Details

4. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Hartmann G, Cheung AK, Piquette-Miller M: Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia. J Pharmacol Exp Ther. 2002 Oct;303(1):273-81. [PubMed:12235261 ]

Enzyme Details

5. 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

References

Hirohashi T, Suzuki H, Takikawa H, Sugiyama Y: ATP-dependent transport of bile salts by rat multidrug resistance-associated protein 3 (Mrp3). J Biol Chem. 2000 Jan 28;275(4):2905-10. [PubMed:10644759 ]

Enzyme Details

6. 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

References

Hartmann G, Cheung AK, Piquette-Miller M: Inflammatory cytokines, but not bile acids, regulate expression of murine hepatic anion transporters in endotoxemia. J Pharmacol Exp Ther. 2002 Oct;303(1):273-81. [PubMed:12235261 ]
Green RM, Hoda F, Ward KL: Molecular cloning and characterization of the murine bile salt export pump. Gene. 2000 Jan 4;241(1):117-23. [PubMed:10607905 ]
Mita S, Suzuki H, Akita H, Stieger B, Meier PJ, Hofmann AF, Sugiyama Y: Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G159-67. Epub 2004 Aug 5. [PubMed:15297262 ]

Enzyme Details

7. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [PubMed:11438506 ]

Enzyme Details

8. 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 ]
Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [PubMed:11438506 ]
Craddock AL, Love MW, Daniel RW, Kirby LC, Walters HC, Wong MH, Dawson PA: Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am J Physiol. 1998 Jan;274(1 Pt 1):G157-69. [PubMed:9458785 ]
Saeki T, Matoba K, Furukawa H, Kirifuji K, Kanamoto R, Iwami K: Characterization, cDNA cloning, and functional expression of mouse ileal sodium-dependent bile acid transporter. J Biochem. 1999 Apr;125(4):846-51. [PubMed:10101301 ]
Saeki T, Takahashi N, Kanamoto R, Iwami K: Characterization of cloned mouse Na+/taurocholate cotransporting polypeptide by transient expression in COS-7 cells. Biosci Biotechnol Biochem. 2002 May;66(5):1116-8. [PubMed:12092825 ]
Walters HC, Craddock AL, Fusegawa H, Willingham MC, Dawson PA: Expression, transport properties, and chromosomal location of organic anion transporter subtype 3. Am J Physiol Gastrointest Liver Physiol. 2000 Dec;279(6):G1188-200. [PubMed:11093941 ]

Enzyme Details

9. 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

References

Hagenbuch B, Stieger B, Foguet M, Lubbert H, Meier PJ: Functional expression cloning and characterization of the hepatocyte Na+/bile acid cotransport system. Proc Natl Acad Sci U S A. 1991 Dec 1;88(23):10629-33. [PubMed:1961729 ]
Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B: Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells. Am J Physiol. 1998 Feb;274(2 Pt 1):G370-5. [PubMed:9486191 ]
Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. [PubMed:12842829 ]
Mita S, Suzuki H, Akita H, Stieger B, Meier PJ, Hofmann AF, Sugiyama Y: Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G159-67. Epub 2004 Aug 5. [PubMed:15297262 ]
Platte HD, Honscha W, Schuh K, Petzinger E: Functional characterization of the hepatic sodium-dependent taurocholate transporter stably transfected into an immortalized liver-derived cell line and V79 fibroblasts. Eur J Cell Biol. 1996 May;70(1):54-60. [PubMed:8738419 ]

Enzyme Details

10. 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

References

Fickert P, Zollner G, Fuchsbichler A, Stumptner C, Pojer C, Zenz R, Lammert F, Stieger B, Meier PJ, Zatloukal K, Denk H, Trauner M: Effects of ursodeoxycholic and cholic acid feeding on hepatocellular transporter expression in mouse liver. Gastroenterology. 2001 Jul;121(1):170-83. [PubMed:11438506 ]
Kullak-Ublick GA, Hagenbuch B, Stieger B, Schteingart CD, Hofmann AF, Wolkoff AW, Meier PJ: Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver. Gastroenterology. 1995 Oct;109(4):1274-82. [PubMed:7557095 ]
Kullak-Ublick GA, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ: Functional characterization of the basolateral rat liver organic anion transporting polypeptide. Hepatology. 1994 Aug;20(2):411-6. [PubMed:8045503 ]
Kanai N, Lu R, Bao Y, Wolkoff AW, Schuster VL: Transient expression of oatp organic anion transporter in mammalian cells: identification of candidate substrates. Am J Physiol. 1996 Feb;270(2 Pt 2):F319-25. [PubMed:8779893 ]
Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. [PubMed:12842829 ]
Jacquemin E, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ: Expression cloning of a rat liver Na(+)-independent organic anion transporter. Proc Natl Acad Sci U S A. 1994 Jan 4;91(1):133-7. [PubMed:8278353 ]
Kouzuki H, Suzuki H, Ito K, Ohashi R, Sugiyama Y: Contribution of organic anion transporting polypeptide to uptake of its possible substrates into rat hepatocytes. J Pharmacol Exp Ther. 1999 Feb;288(2):627-34. [PubMed:9918568 ]
Eckhardt U, Schroeder A, Stieger B, Hochli M, Landmann L, Tynes R, Meier PJ, Hagenbuch B: Polyspecific substrate uptake by the hepatic organic anion transporter Oatp1 in stably transfected CHO cells. Am J Physiol. 1999 Apr;276(4 Pt 1):G1037-42. [PubMed:10198348 ]

Only showing the first 10 proteins. There are 34 proteins in total.

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Showing metabocard for Cholic acid (HMDB0000619)

MOL for HMDB0000619 (Cholic acid)

3D MOL for HMDB0000619 (Cholic acid)

3D SDF for HMDB0000619 (Cholic acid)

3D-SDF for HMDB0000619 (Cholic acid)

PDB for HMDB0000619 (Cholic acid)

3D PDB for HMDB0000619 (Cholic acid)

SMILES for HMDB0000619 (Cholic acid)

INCHI for HMDB0000619 (Cholic acid)

Structure for HMDB0000619 (Cholic acid)

3D Structure for HMDB0000619 (Cholic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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