MiMeDB: Showing metabocard for Cholic acid (MMDBc0000123)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:36:43 UTC

Update Date

2022-08-30 23:57:42 UTC

Metabolite ID

MMDBc0000123

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>
MMDBc0000123

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₂₄H₄₀O₅

Average Mass

408.5714

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fk9-5796000000-2876080f3fa17fb96370	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fk9-5796000000-2876080f3fa17fb96370	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-0439000000-4e43231560df6c61b96d	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-001i-1100049000-86faaffe1dc0eadf9e75	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0000900000-806d3b03c76019afbf7d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0000900000-4edb603ca5534669120e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0000900000-4a76e64b2f0411d0b701	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0001900000-41aa3a7cb25fcf549046	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0057900000-790a3808fa512d5d1687	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0010900000-e6bedfc253363160a37e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0030900000-da4a7bfccbaf1e42171c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0020900000-772055897702843a1d50	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0021900000-0405fe63d70d3a88bf6f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0aou-3844900000-cb3c2aba1b9a29785616	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0007-0019000000-fb9a5b5952cf65eb7988	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0001900000-9583bd9c6c0d2b069b68	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-1027900000-31f3cf065ad48561c0a2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0000900000-b0504ee652d51a711f3a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0000900000-18dd8b6be45775ec83c2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0007-0019000000-285d3d0d87f5471b419a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0007-0019000000-0fcb0f6819b05ab63c12	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0000900000-b0504ee652d51a711f3a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0000900000-18dd8b6be45775ec83c2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0007-0019000000-285d3d0d87f5471b419a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0007-0019000000-0fcb0f6819b05ab63c12	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-6fe7340aea27993f6ecb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4i-0001900000-9e5ac05d22599c16d77a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000900000-a58dbdca74695c9c40e1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-1c1c35b35f948ca53943	2021-09-20	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0596-9642000000-e425981b8a0ac72ea6ee	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)		2014-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Intestine
Kidney
Liver
Placenta
Platelet
Spleen
Urine

Tissue Locations

Intestine
Kidney
Liver
Placenta
Platelet
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191735	Phospholipase A2	Unknown	P04054	Homo sapiens
MMDBp0192108	Solute carrier organic anion transporter family member 1B3	Transporter	Q9NPD5	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0192154	Liver carboxylesterase 1	Enzyme	P23141	Homo sapiens
MMDBp0192406	Alcohol dehydrogenase 1C	Unknown	P00326	Homo sapiens
MMDBp0192658	Acyl-coenzyme A thioesterase 8	Enzyme	O14734	Homo sapiens
MMDBp0192667	Ferrochelatase, mitochondrial	Unknown	P22830	Homo sapiens
MMDBp0193173	Cytochrome c oxidase subunit 1	Unknown	P00395	Homo sapiens
MMDBp0193190	Canalicular multispecific organic anion transporter 1	Transporter	Q92887	Homo sapiens
MMDBp0193300	Multidrug resistance-associated protein 1	Transporter	P33527	Homo sapiens
MMDBp0193395	Canalicular multispecific organic anion transporter 2	Transporter	O15438	Homo sapiens
MMDBp0193400	Bile salt export pump	Transporter	O95342	Homo sapiens
MMDBp0193419	Multidrug resistance protein 1	Transporter	P08183	Homo sapiens
MMDBp0193509	Cytochrome c oxidase subunit 7A1, mitochondrial	Enzyme	P24310	Homo sapiens
MMDBp0193547	Ileal sodium/bile acid cotransporter	Transporter	Q12908	Homo sapiens
MMDBp0193577	Sodium/bile acid cotransporter	Transporter	Q14973	Homo sapiens
MMDBp0193639	Solute carrier organic anion transporter family member 1A2	Transporter	P46721	Homo sapiens
MMDBp0193786	Bile acyl-CoA synthetase	Enzyme	Q9Y2P5	Homo sapiens
MMDBp0193820	Cytochrome c oxidase subunit 5A, mitochondrial	Unknown	P20674	Homo sapiens
MMDBp0193840	Cytochrome c oxidase subunit 6A2, mitochondrial	Enzyme	Q02221	Homo sapiens
MMDBp0193847	Cytochrome c oxidase subunit 7B, mitochondrial	Enzyme	P24311	Homo sapiens
MMDBp0193849	Cytochrome c oxidase subunit 7C, mitochondrial	Enzyme	P15954	Homo sapiens
MMDBp0193853	Cytochrome c oxidase subunit 5B, mitochondrial	Enzyme	P10606	Homo sapiens
MMDBp0193858	Cytochrome c oxidase subunit 6B1	Enzyme	P14854	Homo sapiens
MMDBp0193865	Solute carrier organic anion transporter family member 4A1	Transporter	Q96BD0	Homo sapiens
MMDBp0193866	Cytochrome c oxidase subunit 4 isoform 1, mitochondrial	Enzyme	P13073	Homo sapiens
MMDBp0193892	Cytochrome c oxidase subunit 8A, mitochondrial	Enzyme	P10176	Homo sapiens
MMDBp0193898	Cytochrome c oxidase subunit 6C	Enzyme	P09669	Homo sapiens
MMDBp0193945	Multidrug resistance-associated protein 4	Transporter	O15439	Homo sapiens
MMDBp0194046	Cytochrome c oxidase subunit 3	Enzyme	P00414	Homo sapiens
MMDBp0194047	Cytochrome c oxidase subunit 2	Unknown	P00403	Homo sapiens
MMDBp0195820	Solute carrier family 22 member 7	Transporter	Q9Y694	Homo sapiens
MMDBp0195864	Gastrotropin	Unknown	P51161	Homo sapiens
MMDBp0195892	Ferrochelatase	Enzyme	Q7KZA3	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000469	Cholic acid	Cholic acid	Solute carrier organic anion transporter family, member 1a2	Cholate Transport via Bicarbonate Antiport	VMH	12507753 9007731 9334206
MMDBr0000470	Cholic acid	Cholic acid	Solute carrier family 10 (sodium/bile acid cotransporter), member 1	Cholate Transport via Sodium Symport	VMH	12851823 7592981 8132774 9109432
MMDBr0000471	Adenosine triphosphate	ADP	Atp-binding cassette, sub-family b (mdr/tap), member 11	ABC Bile Acid Transporter	VMH	9738950 9806540 9813153
MMDBr0002605	Adenosine triphosphate	Adenosine monophosphate	Solute carrier family 27 (fatty acid transporter), member 5	Cholate:Coa Ligase (AMP-Forming) Bile Acid Biosynthesis	VMH	10749848 10884298 438652
MMDBr0002785	Cholic acid	Cholic acid	Not Available	Active Transport	VMH	15975683
MMDBr0003552	Cholic acid	Cholic acid	Solute carrier organic anion transporter family, member 1a2	Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.14	VMH	11076394 11076396 14579113
MMDBr0003564	Cholic acid	Cholic acid	Solute carrier organic anion transporter family, member 1a2	Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.14	VMH	11076394 11076396 14579113
MMDBr0003565	Cholic acid	Cholic acid	Solute carrier organic anion transporter family, member 1a2	Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.14	VMH	11076394 11076396 14579113
MMDBr0004095	Choloyl-CoA	Cholic acid	Not Available	Palmitoyl Coenzyme A Hydrolase	VMH	10817395 10944470 11454857 11673457
MMDBr0004096	Choloyl-CoA	Cholic acid	Acyl-coa thioesterase 2	Palmitoyl Coenzyme A Hydrolase	VMH	10817395 10944470 11454857 11673457
MMDBr0004097	Choloyl-CoA	Cholic acid	Acyl-coa thioesterase 4	Palmitoyl Coenzyme A Hydrolase	VMH	10817395 10944470 11454857 11673457
MMDBr0004172	Cholic acid	Deoxycholic acid	Not Available	RE2112C	VMH	11344576 12393855
MMDBr0004173	Cholic acid	Deoxycholic acid	Cytochrome p450, family 7, subfamily a, polypeptide 1	RE2112R	VMH	11344576 12393855
MMDBr0009554	Cholic acid	Cholic acid	Solute carrier family 27 (fatty acid transporter), member 2	Cholate Coenzyme A Ligase	VMH	30371894
MMDBr0009555	Cholic acid	Cholic acid	Solute carrier family 27 (fatty acid transporter), member 2	Cholate Coenzyme A Ligase	VMH	30371894
MMDBr0012371	Cholic acid	3-Dehydrocholic acid; 3oxo-7alpha,12alpha-Dihydroxy-5beta-cholan-24-oic acid	Cytochrome p450, family 3, subfamily a, polypeptide 4	3-dehydrocholic acid formation	VMH	30371894
MMDBr0012623	Glycocholic acid	Cholic acid	Not Available	Glycocholate hydrolysis by bile salt hydrolase (EC 3.5.1.24)	VMH	30371894
MMDBr0012625	Water	Cholic acid	Not Available	Taurocholate hydrolysis by bile salt hydrolase (EC 3.5.1.24)	VMH	30371894
MMDBr0012627	Cholic acid	Cholic acid	Not Available	Bile acid transport, cholate	VMH	30371894
MMDBr0012634	Cholic acid	3-Dehydrocholic acid; 3oxo-7alpha,12alpha-Dihydroxy-5beta-cholan-24-oic acid	Not Available	3-alpha hydroxysteroid dehydrogenase, NAD+ dependent, cholate specific	VMH	30371894
MMDBr0012642	Adenosine triphosphate	Adenosine monophosphate	Not Available	Cholate:CoA ligase (AMP-forming) (EC:6.2.1.7) cytoplasmic	VMH	30371894
MMDBr0013284	Cholic acid	3alpha,7alpha-dihydroxy-12-oxo-5beta-cholanic acid	Not Available	Dehydrogenation	RHEA	34755880
MMDBr0013322	Choloyl-CoA	Cholic acid	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0013323	Choloyl-CoA	Cholic acid	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0013857	Glycocholic acid	Cholic acid	Conjugated bile acid hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0013858	Glycocholic acid	Cholic acid	Conjugated bile acid hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0013867	Cholic acid	3alpha,12alpha-dihydroxy-7-oxo-5beta-cholanic acid	7alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0013868	Cholic acid	3alpha,12alpha-dihydroxy-7-oxo-5beta-cholanic acid	7alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0014349	Adenosine triphosphate	Adenosine monophosphate	Bile acid--coenzyme A ligase	Ligation; Synthesis	RHEA	34755880
MMDBr0014350	Adenosine triphosphate	Adenosine monophosphate	Bile acid--coenzyme A ligase	Ligation; Synthesis	RHEA	34755880
MMDBr0016276	Cholic acid	Water	Conjugated bile acid hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0016277	Water	Cholic acid	Conjugated bile acid hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0016304	Cholic acid	7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid	3alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016305	Cholic acid	7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid	3alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016316	Cholic acid	7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid	3alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016317	Cholic acid	7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid	3alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016387	Cholic acid	3alpha,12alpha-dihydroxy-7-oxo-5beta-cholanic acid	7alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016388	Cholic acid	3alpha,12alpha-dihydroxy-7-oxo-5beta-cholanic acid	7alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016445	Cholic acid	Choloyl-CoA	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016446	Cholic acid	Choloyl-CoA	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016447	Cholic acid	Choloyl-CoA	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016448	Cholic acid	Choloyl-CoA	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016676	allodeoxycholoyl-CoA	allodeoxycholic acid	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016677	allodeoxycholoyl-CoA	allodeoxycholic acid	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Biliary atresia		Association	Human Urine	HMDB	3944741
Biliary atresia	Increased	Association	Human Blood	HMDB	16553252
Cirrhosis		Association	Human Urine	HMDB	2621422
Cystic fibrosis		Association	Human Blood	HMDB	15185309
Primary biliary cirrhosis		Association	Human Urine	HMDB	2621422
Primary biliary cirrhosis	Increased	Association	Human Blood	HMDB	2621422
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	149	Human feces; Human ; Human urine; Human mucosa; Human saliva; Human sputum; Human subgingival plaque; Pig	Microbial culture; Metabolic reconstruction; Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	76	Human feces; Human stool; Human ; Human urine; Human appendix biopsy; Human saliva	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	76	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human unknown; Human pleural fluid plaque	Microbial culture; Metabolic reconstruction
Bacteria	Actinobacteria	95	Human ; Human feces; Human saliva; Human mucosa; Human stool	Microbial culture; Metabolic reconstruction
Archaea	Euryarchaeota	3	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Fusobacteria	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria/NULL	Firmicutes	1	Human feces; Human ; Human urine; Human mucosa; Human saliva; Human sputum; Human subgingival plaque; Pig	Microbial culture; Metabolic reconstruction; Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Species	Data Source	Reference
Animal	Eucheuma	FooDB	31437929
Animal	Saccharina japonica	FooDB	31437929
Animal	Spirulina	FooDB	31437929
Animal	Lota lota	FooDB	31437929
Animal	Porphyra umbilicalis	FooDB	31437929
Animal	Chondrus crispus	FooDB	31437929
Animal	Laminaria	FooDB	31437929
Animal	Strombidae	FooDB	31437929
Animal	Haliotis	FooDB	31437929
Animal	Clupea harengus harengus	FooDB	31437929
Animal	Undaria pinnatifida	FooDB	31437929
Animal	Peprilus triacanthus	FooDB	31437929
Animal	Rhodophyta	FooDB	31437929
Animal	Myoxocephalus	FooDB	31437929
Plant	Allium fistulosum	FooDB	31437929
Plant	Prunus armeniaca	FooDB	31437929
Plant	Capsicum	FooDB	31437929
Plant	Nelumbo nucifera	FooDB	31437929
Plant	Cymbopogon citratus	FooDB	31437929
Plant	Luffa aegyptiaca	FooDB	31437929
Plant	Lupinus	FooDB	31437929
Plant	Citrus reticulata	FooDB	31437929
Plant	Tilia cordata	FooDB	31437929
Plant	Bertholletia excelsa	FooDB	31437929
Plant	Ceratonia siliqua	FooDB	31437929
Plant	Vaccinium alaskaense	FooDB	31437929
Plant	Durio zibethinus	FooDB	31437929
Plant	Brassica rapa var. rapa	FooDB	31437929
Plant	Ribes glandulosum	FooDB	31437929
Plant	Coriandrum sativum	FooDB	31437929
Plant	Anethum graveolens	FooDB	31437929
Plant	Verbena officinalis	FooDB	31437929
Plant	Carthamus tinctorius	FooDB	31437929
Plant	Vaccinium oxycoccos	FooDB	31437929
Plant	Cicer arietinum	FooDB	31437929
Plant	Prunus persica var. nucipersica	FooDB	31437929
Plant	Aloysia triphylla	FooDB	31437929
Plant	Anacardium occidentale	FooDB	31437929
Plant	Vaccinium parvifolium	FooDB	31437929
Plant	Capsicum chinense	FooDB	31437929
Plant	Oenothera biennis	FooDB	31437929
Plant	Brassica napus var. pabularia	FooDB	31437929
Plant	Eriobotrya japonica	FooDB	31437929
Plant	Diospyros kaki	FooDB	31437929
Plant	Vaccinium reticulatum	FooDB	31437929
Plant	Virola surinamensis	FooDB	31437929
Plant	Theobroma cacao	FooDB	31437929
Plant	Solanum quitoense	FooDB	31437929
Plant	Rumex acetosa	FooDB	31437929
Plant	Pyrus pyrifolia	FooDB	31437929
Plant	Satureja montana	FooDB	31437929
Plant	Vaccinium arboreum	FooDB	31437929
Plant	Perideridia oregana	FooDB	31437929
Plant	Brassica oleracea var. capitata	FooDB	31437929
Plant	Wasabia japonica	FooDB	31437929
Plant	Origanum onites	FooDB	31437929
Plant	Theobroma grandiflorum	FooDB	31437929
Plant	Vigna unguiculata ssp. cylindrica	FooDB	31437929
Plant		FooDB	31437929
Plant	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant	Citrus japonica	FooDB	31437929
Plant	Ginkgo biloba	FooDB	31437929
Plant	Vaccinium myrtillus	FooDB	31437929
Plant	Camellia sinensis	FooDB	31437929
Plant	Flammulina velutipes	FooDB	31437929
Plant	Syzygium aromaticum	FooDB	31437929
Plant	Viburnum edule	FooDB	31437929
Plant	Phaseolus vulgaris	FooDB	31437929
Plant	Pouteria sapota	FooDB	31437929
Plant	Vaccinium uliginosum	FooDB	31437929
Plant	Vicia faba	FooDB	31437929
Plant	Prunus avium	FooDB	31437929
Plant	Daucus carota ssp. sativus	FooDB	31437929
Plant	Piper nigrum	FooDB	31437929
Plant	Raphanus sativus var. sativus	FooDB	31437929
Plant	Prunus persica var. persica	FooDB	31437929
Plant	Dioscorea	FooDB	31437929
Plant	Momordica charantia	FooDB	31437929
Plant	Rubus ursinus x idaeus	FooDB	31437929
Plant	Origanum vulgare	FooDB	31437929
Plant	Vitis vinifera	FooDB	31437929
Plant	Cirsium	FooDB	31437929
Plant	Castanea	FooDB	31437929
Plant	Opuntia	FooDB	31437929
Plant	Raphanus sativus var. niger	FooDB	31437929
Plant	Capsicum annuum	FooDB	31437929
Plant	Dysphania ambrosioides	FooDB	31437929
Plant	Photinia melanocarpa	FooDB	31437929
Plant	Pleurotus ostreatus	FooDB	31437929
Plant	Colocasia esculenta	FooDB	31437929
Plant	Nuphar lutea	FooDB	31437929
Plant	Anthriscus cerefolium	FooDB	31437929
Plant	Pachyrhizus erosus	FooDB	31437929
Plant	Lupinus albus	FooDB	31437929
Plant	Solanum melongena	FooDB	31437929
Plant	Syzygium jambos	FooDB	31437929
Plant	Salix pulchra	FooDB	31437929
Plant	Cichorium endivia	FooDB	31437929
Plant	Myristica fragrans	FooDB	31437929
Plant	Elaeis	FooDB	31437929
Plant	Cinnamomum	FooDB	31437929
Plant	Citrus maxima	FooDB	31437929
Plant	Feijoa sellowiana	FooDB	31437929
Plant	Vaccinium ovatum	FooDB	31437929
Plant	Ribes uva-crispa	FooDB	31437929
Plant	Brassica oleracea var. italica	FooDB	31437929
Plant	Crocus sativus	FooDB	31437929
Plant	Thymus pulegioides	FooDB	31437929
Plant	Vaccinium	FooDB	31437929
Plant	Fagus	FooDB	31437929
Plant	Mespilus germanica	FooDB	31437929
Plant	Lablab purpureus	FooDB	31437929
Plant	Cydonia oblonga	FooDB	31437929
Plant	Brassica rapa var. perviridis	FooDB	31437929
Plant	Rheum rhabarbarum	FooDB	31437929
Plant	Castanea sativa	FooDB	31437929
Plant	Salvia officinalis	FooDB	31437929
Plant	Phaseolus coccineus	FooDB	31437929
Plant	Apium graveolens	FooDB	31437929
Plant	Opuntia cochenillifera	FooDB	31437929
Plant	Salvia elegans	FooDB	31437929
Plant	Mentha	FooDB	31437929
Plant	Mentha aquatica	FooDB	31437929
Plant	Annona muricata	FooDB	31437929
Plant	Cucurbita	FooDB	31437929
Plant	Sagittaria latifolia	FooDB	31437929
Plant	Cocos nucifera	FooDB	31437929
Plant	Tamarindus indica	FooDB	31437929
Plant	Syzygium cumini	FooDB	31437929
Plant	Empetrum nigrum	FooDB	31437929
Plant	Typha angustifolia	FooDB	31437929
Plant	Myrica rubra	FooDB	31437929
Plant	Tilia tomentosa	FooDB	31437929
Plant	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Vaccinium angustifolium x vaccinium corymbosum	FooDB	31437929
Plant	Sambucus	FooDB	31437929
Plant	Valerianella locusta	FooDB	31437929
Plant	Pinus	FooDB	31437929
Plant	Sisymbrium	FooDB	31437929
Plant	Olea europaea	FooDB	31437929
Plant	Vanilla	FooDB	31437929
Plant	Angelica keiskei	FooDB	31437929
Plant	Borago officinalis	FooDB	31437929
Plant	Psidium guajava	FooDB	31437929
Plant	Carya	FooDB	31437929
Plant	Hyssopus officinalis	FooDB	31437929
Plant	Vaccinium vitis-idaea	FooDB	31437929
Plant	Physalis philadelphica var. immaculata	FooDB	31437929
Plant	Scorzonera hispanica	FooDB	31437929
Plant	Vigna unguiculata ssp. sesquipedalis	FooDB	31437929
Plant	Rubus spectabilis	FooDB	31437929
Plant	Ipomoea aquatica	FooDB	31437929
Plant	Manihot esculenta	FooDB	31437929
Plant	Daucus carota	FooDB	31437929
Plant	Solanum tuberosum	FooDB	31437929
Plant	Raphanus sativus	FooDB	31437929
Plant	Beta vulgaris ssp. cicla	FooDB	31437929
Plant	Prunus dulcis	FooDB	31437929
Plant	Vigna radiata	FooDB	31437929
Plant	Cuminum cyminum	FooDB	31437929
Plant	Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant	Cantharellus cibarius	FooDB	31437929
Plant	Allium sativum	FooDB	31437929
Plant	Musa x paradisiaca	FooDB	31437929
Plant	Sinapis alba	FooDB	31437929
Plant	Morus nigra	FooDB	31437929
Plant	Opuntia macrorhiza	FooDB	31437929
Plant	Brassica ruvo	FooDB	31437929
Plant	Fragaria x ananassa	FooDB	31437929
Plant	Pinus edulis	FooDB	31437929
Plant	Apium graveolens var. secalinum	FooDB	31437929
Plant	Rubus idaeus	FooDB	31437929
Plant	Arachis hypogaea	FooDB	31437929
Plant	Passiflora edulis	FooDB	31437929
Plant	Pyrus communis	FooDB	31437929
Plant	Allium cepa	FooDB	31437929
Plant	Manilkara zapota	FooDB	31437929
Plant	Abelmoschus esculentus	FooDB	31437929
Plant	Moringa oleifera	FooDB	31437929
Plant	Solanum lycopersicum	FooDB	31437929
Plant	Illicium verum	FooDB	31437929
Plant		FooDB	31437929
Plant	Vigna angularis	FooDB	31437929
Plant	Malus	FooDB	31437929
Plant	Auricularia auricula-judae	FooDB	31437929
Plant	Corylus	FooDB	31437929
Plant	Juglans ailanthifolia	FooDB	31437929
Plant	Juglans	FooDB	31437929
Plant	Chamaemelum nobile	FooDB	31437929
Plant	Cucurbita pepo var. clypeata	FooDB	31437929
Plant	Sambucus nigra	FooDB	31437929
Plant	Mangifera indica	FooDB	31437929
Plant	Polygonum alpinum	FooDB	31437929
Plant	Hippophae rhamnoides	FooDB	31437929
Plant	Melissa officinalis	FooDB	31437929
Plant	Mentha spicata	FooDB	31437929
Plant	Helianthus annuus	FooDB	31437929
Plant	Auricularia polytricha	FooDB	31437929
Plant	Attalea speciosa	FooDB	31437929
Plant	Laurus nobilis	FooDB	31437929
Plant	Pediomelum esculentum	FooDB	31437929
Plant	Petroselinum crispum	FooDB	31437929
Plant	Rubus arcticus	FooDB	31437929
Plant	Ribes nigrum	FooDB	31437929
Plant	Zingiber officinale	FooDB	31437929
Plant	Brassica juncea	FooDB	31437929
Plant	Chrysanthemum coronarium	FooDB	31437929
Plant	Eleocharis dulcis	FooDB	31437929
Plant	Pisum sativum	FooDB	31437929
Plant	Camellia oleifera	FooDB	31437929
Plant	Vaccinium corymbosum	FooDB	31437929
Plant	Rumex articus	FooDB	31437929
Plant	Actinidia chinensis	FooDB	31437929
Plant	Ribes aureum var. villosum	FooDB	31437929
Plant	Pimenta dioica	FooDB	31437929
Plant	Thymus vulgaris	FooDB	31437929
Plant	Canarium ovatum	FooDB	31437929
Plant	Medicago sativa	FooDB	31437929
Plant	Spinacia oleracea	FooDB	31437929
Plant	Agaricus bisporus	FooDB	31437929
Plant	Eruca vesicaria ssp. sativa	FooDB	31437929
Plant	Hibiscus sabdariffa	FooDB	31437929
Plant	Carica papaya	FooDB	31437929
Plant	Cajanus cajan	FooDB	31437929
Plant	Origanum majorana	FooDB	31437929
Plant	Benincasa hispida	FooDB	31437929
Plant	Metroxylon sagu	FooDB	31437929
Plant	Vigna mungo	FooDB	31437929
Plant	Armoracia rusticana	FooDB	31437929
Plant	Vitis rotundifolia	FooDB	31437929
Plant	Juglans cinerea	FooDB	31437929
Plant	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Cyathea	FooDB	31437929
Plant	Arctium lappa	FooDB	31437929
Plant	Morus	FooDB	31437929
Plant	Brassica oleracea var. gongylodes	FooDB	31437929
Plant	Prunus persica	FooDB	31437929
Plant	Brassica oleracea var. gemmifera	FooDB	31437929
Plant	Foeniculum vulgare	FooDB	31437929
Plant	Artocarpus altilis	FooDB	31437929
Plant	Psidium cattleianum	FooDB	31437929
Plant	Vaccinium macrocarpon	FooDB	31437929
Plant	Vitis labrusca	FooDB	31437929
Plant	Vigna unguiculata	FooDB	31437929
Plant	Brosimum alicastrum	FooDB	31437929
Plant	Cynara scolymus	FooDB	31437929
Plant	Castanea mollissima	FooDB	31437929
Plant	Phoenix dactylifera	FooDB	31437929
Plant	Myrica	FooDB	31437929
Plant	Cucumis metuliferus	FooDB	31437929
Plant	Lentinus edodes	FooDB	31437929
Plant	Prunus cerasus	FooDB	31437929
Plant	Citrus x paradisi	FooDB	31437929
Plant	Nephelium lappaceum	FooDB	31437929
Plant	Rosmarinus officinalis	FooDB	31437929
Plant	Artemisia vulgaris	FooDB	31437929
Plant	Phytolacca americana	FooDB	31437929
Plant	Lepidium sativum	FooDB	31437929
Plant	Tetragonia tetragonioides	FooDB	31437929
Plant	Vaccinium angustifolium	FooDB	31437929
Plant	Castanea crenata	FooDB	31437929
Plant	Helianthus tuberosus	FooDB	31437929
Plant	Grifola frondosa	FooDB	31437929
Plant	Thelesperma	FooDB	31437929
Plant	Ficus carica	FooDB	31437929
Plant	Quercus	FooDB	31437929
Plant	Corylus avellana	FooDB	31437929
Plant		FooDB	31437929
Plant	Beta vulgaris var. rubra	FooDB	31437929
Plant	Vaccinium elliottii	FooDB	31437929
Plant	Chamerion angustifolium	FooDB	31437929
Plant	Litchi chinensis	FooDB	31437929
Plant	Malpighia emarginata	FooDB	31437929
Plant	Physalis	FooDB	31437929
Plant	Levisticum officinale	FooDB	31437929
Plant	Ziziphus zizyphus	FooDB	31437929
Plant	Juglans regia	FooDB	31437929
Plant	Trigonella foenum-graecum	FooDB	31437929
Plant	Dimocarpus longan	FooDB	31437929
Plant	Pangium edule	FooDB	31437929
Plant	Brassica oleracea var. sabauda	FooDB	31437929
Plant	Matricaria recutita	FooDB	31437929
Plant	Cynara cardunculus	FooDB	31437929
Plant	Asparagus officinalis	FooDB	31437929
Plant	Brassica napus	FooDB	31437929
Plant	Hedysarum alpinum	FooDB	31437929
Plant	Salvia hispanica	FooDB	31437929
Plant	Artemisia dracunculus	FooDB	31437929
Plant	Agave	FooDB	31437929
Plant	Pimpinella anisum	FooDB	31437929
Plant	Apium graveolens var. dulce	FooDB	31437929
Plant	Citrus aurantiifolia	FooDB	31437929
Plant	Vigna aconitifolia	FooDB	31437929
Plant	Brassica oleracea var. viridis	FooDB	31437929
Plant	Vitellaria paradoxa	FooDB	31437929
Plant	Allium	FooDB	31437929
Plant		FooDB	31437929
Plant	Capsicum baccatum var. baccatum	FooDB	31437929
Plant	Lactuca sativa	FooDB	31437929
Plant	Xanthosoma sagittifolium	FooDB	31437929
Plant	Eragrostis tef	FooDB	31437929
Plant	Diospyros	FooDB	31437929
Plant	Brassica alboglabra	FooDB	31437929
Plant	Mammea americana	FooDB	31437929
Plant	Pistacia vera	FooDB	31437929
Plant	Amaranthus	FooDB	31437929
Plant	Basella alba	FooDB	31437929
Plant	Annona squamosa	FooDB	31437929
Plant	Punica granatum	FooDB	31437929
Plant	Capsicum pubescens	FooDB	31437929
Plant	Beta vulgaris	FooDB	31437929
Plant	Gossypium	FooDB	31437929
Plant	Crateva religiosa	FooDB	31437929
Plant	Byrsonima crassifolia	FooDB	31437929
Plant	Vitis aestivalis	FooDB	31437929
Plant	Eugenia javanica	FooDB	31437929
Plant	Mentha arvensis	FooDB	31437929
Plant	Vitis	FooDB	31437929
Plant	Vaccinium stamineum	FooDB	31437929
Plant	Citrus latifolia	FooDB	31437929
Plant	Carya illinoinensis	FooDB	31437929
Plant	Grataegosorbus mitschurinii	FooDB	31437929
Plant	Solanum lycopersicum var. cerasiforme	FooDB	31437929
Plant		FooDB	31437929
Plant	Malus pumila	FooDB	31437929
Plant	Brassica rapa var. chinensis	FooDB	31437929
Plant	Origanum x majoricum	FooDB	31437929
Plant	Psophocarpus tetragonolobus	FooDB	31437929
Plant	Portulaca oleracea	FooDB	31437929
Plant	Cucumis sativus	FooDB	31437929
Plant	Diospyros virginiana	FooDB	31437929
Plant	Cinnamomum aromaticum	FooDB	31437929
Plant	Ribes rubrum	FooDB	31437929
Plant	Ipomoea batatas	FooDB	31437929
Plant	Allium ampeloprasum	FooDB	31437929
Plant	Chenopodium album	FooDB	31437929
Plant		FooDB	31437929
Plant	Rumex	FooDB	31437929
Plant	Cucurbita maxima	FooDB	31437929
Plant	Sechium edule	FooDB	31437929
Plant	Rubus chamaemorus	FooDB	31437929
Plant	Brassica oleracea	FooDB	31437929
Plant	Eugenia uniflora	FooDB	31437929
Plant	Citrullus lanatus var. fistulosus	FooDB	31437929
Plant	Pastinaca sativa	FooDB	31437929
Plant	Tragopogon porrifolius	FooDB	31437929
Plant	Rubus x loganobaccus	FooDB	31437929
Plant	Ribes x nidigrolaria	FooDB	31437929
Plant	Allium ascalonicum	FooDB	31437929
Plant	Lactuca sativa l. var. longifolia	FooDB	31437929
Plant	Amelanchier alnifolia	FooDB	31437929
Plant	Sesbania bispinosa	FooDB	31437929
Plant	Curcuma longa	FooDB	31437929
Plant	Taraxacum officinale	FooDB	31437929
Plant	Garcinia mangostana	FooDB	31437929
Plant	Annona reticulata	FooDB	31437929
Plant	Allium tuberosum	FooDB	31437929
Plant	Elettaria cardamomum	FooDB	31437929
Plant	Lathyrus sativus	FooDB	31437929
Plant	Dioscorea pentaphylla	FooDB	31437929
Plant	Gaylussacia baccata	FooDB	31437929
Plant	Persea americana	FooDB	31437929
Plant	Petasites japonicus	FooDB	31437929
Plant	Corchorus olitorius	FooDB	31437929
Plant	Brassica oleracea var. botrytis	FooDB	31437929
Plant	Cichorium intybus	FooDB	31437929
Plant	Matteuccia struthiopteris	FooDB	31437929
Plant	Chenopodium quinoa	FooDB	31437929
Plant	Prunus tomentosa	FooDB	31437929
Plant	Vaccinium myrtilloides	FooDB	31437929
Plant	Ananas comosus	FooDB	31437929
Plant	Tilia	FooDB	31437929
Plant	Maranta arundinacea	FooDB	31437929
Plant	Cucumis melo	FooDB	31437929
Plant	Juglans nigra	FooDB	31437929
Plant	Cinnamomum verum	FooDB	31437929
Plant	Brassica oleracea var. conica	FooDB	31437929
Plant	Mentha x piperita	FooDB	31437929
Plant	Cucurbita moschata	FooDB	31437929
Plant	Nelumbo	FooDB	31437929
Plant	Lippia graveolens	FooDB	31437929
Plant	Macadamia	FooDB	31437929
Plant	Rosa	FooDB	31437929
Plant	Apium graveolens var. rapaceum	FooDB	31437929
Plant	Papaver	FooDB	31437929
Plant	Ocimum basilicum	FooDB	31437929
Plant	Capsicum annuum var. annuum	FooDB	31437929
Plant	Citrus limon	FooDB	31437929
Plant	Vaccinium deliciosum	FooDB	31437929
Plant	Brassica rapa var. pekinensis	FooDB	31437929
Plant	Annona cherimola	FooDB	31437929
Plant	Brassica rapa	FooDB	31437929
Plant	Capparis spinosa	FooDB	31437929
Plant	Prunus	FooDB	31437929
Plant	Glycine max	FooDB	31437929
Plant	Sesamum orientale	FooDB	31437929
Plant	Prunus virginiana	FooDB	31437929
Plant	Macadamia tetraphylla	FooDB	31437929
Plant	Artocarpus heterophyllus	FooDB	31437929
Plant	Carissa macrocarpa	FooDB	31437929
Plant	Sorbus aucuparia	FooDB	31437929
Plant	Lens culinaris	FooDB	31437929
Plant	Phaseolus lunatus	FooDB	31437929
Plant	Satureja hortensis	FooDB	31437929
Plant	Lagenaria siceraria	FooDB	31437929
Plant	Citrus sinensis	FooDB	31437929
Plant	Musa acuminata	FooDB	31437929
Plant	Brassica oleracea var. costata	FooDB	31437929
Plant	Panax	FooDB	31437929
Plant	Vigna unguiculata ssp. unguiculata	FooDB	31437929
Plant	Phyllostachys edulis	FooDB	31437929
Plant	Linum usitatissimum	FooDB	31437929
Plant	Citrullus lanatus	FooDB	31437929
Plant	Vigna umbellata	FooDB	31437929
Plant	Averrhoa carambola	FooDB	31437929
Plant	Prunus domestica	FooDB	31437929
Plant	Carum carvi	FooDB	31437929
Plant	Allium schoenoprasum	FooDB	31437929
Plant	Rubus occidentalis	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.075	0.090			umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	HMDB	3944741
Human Blood	Detected and Quantified	15.6	3.6			uM	Newborn (0-30 days old)	Both	Extrahepatic biliary atresia (EHBA)	HMDB	16553252
Human Urine	Detected and Quantified	1.9		0.11	7.2	umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	2.2		0.13	6.6	umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Blood	Detected and Quantified	1.52	0.26			uM	Children (1-13 years old)	Both	Cystic fibrosis	HMDB	15185309
Human Blood	Detected and Quantified	1.71	0.29			uM	Adult (>18 years old)	Both	Cystic fibrosis	HMDB	15185309
Human Blood	Detected and Quantified	13.8		1.2	36.5	uM	Adult (>18 years old)	Both	Primary biliary cirrhosis	HMDB	2621422
Human Blood	Detected and Quantified	48.5		2.8	124.5	uM	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Blood	Detected and Quantified	0.1		0	0.1	uM	Infant (0-1 year old)	Both	Normal	HMDB	27163928
Human Blood	Detected and Quantified	0.72	0.24			uM	Adult (>18 years old)	Both	Normal	HMDB	15185309
Human Blood	Detected and Quantified	1.7	0.3			uM	Newborn (0-30 days old)	Both	Normal	HMDB	16553252
Human Bile	Detected and Quantified	32060		31830	32280	uM	Adult (>18 years old)	Both	Normal	HMDB	16548228
Human Feces	Detected and Quantified	44.71	47.79			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Urine	Detected and Quantified	1.969	0.612			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	18085514
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000619

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/0009-8981(76)90173-x. [PubMed:1000848 ]
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. doi: 10.1056/NEJM197506052922303. [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. doi: 10.1172/JCI115601. [PubMed:1371123 ]
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. doi: 10.3109/00365519209088378. [PubMed:1514020 ]
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. doi: 10.1016/0378-4274(92)90156-e. [PubMed:1641875 ]
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 ]
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. doi: 10.3109/00365518909089081. [PubMed:2727621 ]
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. doi: 10.1172/JCI112030. [PubMed:4031069 ]
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 ]
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. doi: 10.1055/s-2008-1070108. [PubMed:7106004 ]
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 ]
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 ]
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. doi: 10.1136/gut.45.3.446. [PubMed:10446117 ]
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. doi: 10.1242/jeb.204.10.1673. [PubMed:11316487 ]
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 ]
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. doi: 10.1152/ajpgi.00417.2002. [PubMed:12576301 ]
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. doi: 10.1053/plac.2002.0959. [PubMed:12744922 ]
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. doi: 10.1002/hep.20238. [PubMed:15185309 ]
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. doi: 10.1161/01.ATV.0000178994.21828.a7. Epub 2005 Jul 21. [PubMed:16037564 ]
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 ]
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. doi: 10.3109/2000-1967-017. [PubMed:16553252 ]

Showing metabocard for Cholic acid (MMDBc0000123)

MOL for #<Metabolite:0x00007fe2d4c41990>

3D MOL for #<Metabolite:0x00007fe2d4c41990>

3D SDF for #<Metabolite:0x00007fe2d4c41990>

3D-SDF for #<Metabolite:0x00007fe2d4c41990>

PDB for #<Metabolite:0x00007fe2d4c41990>

3D PDB for #<Metabolite:0x00007fe2d4c41990>

SMILES for #<Metabolite:0x00007fe2d4c41990>

INCHI for #<Metabolite:0x00007fe2d4c41990>

Structure for #<Metabolite:0x00007fe2d4c41990>

3D Structure for #<Metabolite:0x00007fe2d4c41990>