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Showing metabocard for Cholic acid (HMDB0000619)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (21)transporters (13) Show 34 proteinsXML
enzymes (21)transporters (13) Show 34 proteins
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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:04 UTC
HMDB IDHMDB0000619
Secondary Accession Numbers
  • HMDB00619
Metabolite Identification
Common NameCholic acid
DescriptionCholic 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000619 (Cholic acid)

  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
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 13  1  1  6  0  0  0
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 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
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3D MOL for HMDB0000619 (Cholic acid)

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
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    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
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   -4.9308   -2.1699   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
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 11 12  1  0
 12 13  1  0
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 17 18  1  6
 13 19  1  0
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 17  8  1  0
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  1 30  1  0
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  1 32  1  0
  2 33  1  1
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  7 38  1  0
  8 39  1  1
  9 40  1  0
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 11 44  1  1
 12 45  1  6
 13 46  1  1
 14 47  1  0
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 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
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3D SDF for HMDB0000619 (Cholic acid)

  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

$$$$
Download

3D-SDF for HMDB0000619 (Cholic acid)

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
Download

PDB for HMDB0000619 (Cholic acid)

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
Download

3D PDB for HMDB0000619 (Cholic acid)

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
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SMILES for HMDB0000619 (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
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INCHI for HMDB0000619 (Cholic acid)

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
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC24H40O5
Average Molecular Weight408.5714
Monoisotopic Molecular Weight408.28757439
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 Number81-25-4
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 KeyBHQCQFFYRZLCQQ-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point197 - 201 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.18 mg/mLNot Available
LogP2.02RODA,A ET AL. (1990)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker204.62730932474
[M-H]-MetCCS_train_neg200.72430932474
[M-H]-Not Available202.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000201
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Bile
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Intestine
  • Kidney
  • Liver
  • Placenta
  • Platelet
  • Spleen
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Cystic fibrosis
  1. 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
  1. 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 ]
  2. 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
  1. 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 ]
  2. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB02659
Phenol Explorer Compound IDNot Available
FooDB IDFDB012810
KNApSAcK IDNot Available
Chemspider ID192176
KEGG Compound IDC00695
BioCyc IDCHOLATE
BiGG ID35720
Wikipedia LinkCholic_Acid
METLIN ID206
PubChem Compound221493
PDB IDNot Available
ChEBI ID16359
Food Biomarker OntologyNot Available
VMH IDCHOLATE
MarkerDB IDMDB00000202
Good Scents IDNot Available
References
Synthesis ReferenceCalimente, Daniel. Synthesis and characterization of new naphthalimide and cholic acid-containing complexing agents. (1998), 104 pp.
Material Safety Data Sheet (MSDS)Not Available
General References

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
  1. 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
  1. 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
  1. 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 Adetails
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
  1. 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 ]
  2. 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 ]
  3. 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
  1. 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
  1. 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-CoAdetails
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
  1. 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
  1. 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
  1. 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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
  1. 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
  1. 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
  1. 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
  1. 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 ]
  2. 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 ]
  3. 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
  1. 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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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