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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5)transporters (8) Show 13 proteins XML

enzymes (5)transporters (8) Show 13 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:03 UTC

HMDB ID

HMDB0000518

Secondary Accession Numbers

HMDB00518

Metabolite Identification

Common Name

Chenodeoxycholic acid

Description

Chenodeoxycholic acid is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). Usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.

Structure

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


  Mrv1652305271900052D          

 33 36  0  0  1  0            999 V2000
   12.1249   -7.6292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1249   -8.4368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6963   -8.4368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4261   -8.8327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9820   -8.8327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9091   -7.3730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4261   -7.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6963   -7.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9091   -8.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3750   -8.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4261   -9.6712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9820   -9.6712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6963  -10.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9091   -6.5268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1249   -6.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9820   -8.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2832   -8.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3454   -6.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6390   -6.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2832  -10.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1560   -5.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0520   -6.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5612   -8.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5612   -9.6644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1249   -9.2675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4339   -8.0175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6963   -9.2675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6312   -6.9693    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9779  -10.3883    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7802   -6.6071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1752   -5.3559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9818   -9.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9976   -9.8804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  1 15  1  1  0  0  0
  4  2  1  0  0  0  0
  9  2  1  0  0  0  0
  2 25  1  6  0  0  0
  8  3  1  0  0  0  0
  5  3  1  0  0  0  0
  4  3  1  0  0  0  0
  3 27  1  6  0  0  0
 11  4  1  0  0  0  0
  4 26  1  1  0  0  0
 12  5  1  0  0  0  0
  5 16  1  1  0  0  0
 17  5  1  0  0  0  0
 10  6  1  0  0  0  0
 14  6  1  0  0  0  0
  6 28  1  6  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 13 11  1  0  0  0  0
 20 12  1  0  0  0  0
 13 12  1  0  0  0  0
 19 14  1  0  0  0  0
 14 21  1  6  0  0  0
 23 17  1  0  0  0  0
 19 18  1  0  0  0  0
 22 18  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 12 29  1  1  0  0  0
 30 22  2  0  0  0  0
 31 22  1  0  0  0  0
 24 32  1  6  0  0  0
 11 33  1  6  0  0  0
M  END

HMDB0000518
     RDKit          3D
Chenodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
    3.9687    1.7666   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8618    0.2701   -0.3380 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9494   -0.3652   -1.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3406   -0.0316   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7437   -0.4122    0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9708   -1.0154    1.3442 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0104   -0.0987    1.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -0.2422   -0.9008 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5885   -1.7702   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649   -2.1924   -0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3810   -0.9554   -0.6534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9225   -0.9087    0.1001 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5782    0.3982   -0.3012 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6813    1.5813   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7053    1.4325   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3482    0.1255   -0.1422 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4456   -0.0403    1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9340    0.5936    0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8119    1.4667    1.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8155    1.2321   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0794    1.6660   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7608    0.6033    0.7010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0252    0.3941    0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436   -0.6704    0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843   -0.6998    0.7039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2424   -1.8223   -0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7874   -2.0124   -0.4693 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5276   -2.0228   -1.8601 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0014    2.1383   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6176    2.2557    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3914    2.1962   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0178   -0.0091    0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376   -0.0423   -2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -1.4857   -1.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162    1.0294   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0184   -0.6221   -1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3821    0.8182    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    0.0707   -1.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697   -1.9872    0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939   -2.2547   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8812   -2.9373   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -2.7152    0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1776   -0.7279   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7962   -0.9943    1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733    0.3346   -1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1485    2.4487   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6381    1.8897    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8185    1.5467   -1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110    2.2542   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3204    0.4629    1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5487    0.4329    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4231   -1.1012    1.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    1.5172    2.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5617    2.5169    1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0434    1.0025    2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3483    2.1343   -1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0257    0.5118   -1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8136    2.5628    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7316    2.1124   -0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0472    1.0619    1.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4816   -0.3093    0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5640   -1.4490    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2735   -1.0404    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -1.0158    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8126   -1.6492   -1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6643   -2.7510    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232   -3.0209   -0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877   -1.4553   -2.3389 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
 16 17  1  1
 13 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 16  8  1  0
 25 18  1  0
 16 11  1  0
 27 12  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 13 45  1  6
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 19 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  1
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  1
 26 65  1  0
 26 66  1  0
 27 67  1  1
 28 68  1  0
M  END


  Mrv1652305271900052D          

 33 36  0  0  1  0            999 V2000
   12.1249   -7.6292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1249   -8.4368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6963   -8.4368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4261   -8.8327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9820   -8.8327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9091   -7.3730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4261   -7.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6963   -7.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9091   -8.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3750   -8.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4261   -9.6712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9820   -9.6712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6963  -10.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9091   -6.5268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1249   -6.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9820   -8.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2832   -8.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3454   -6.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6390   -6.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2832  -10.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1560   -5.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0520   -6.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5612   -8.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5612   -9.6644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1249   -9.2675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4339   -8.0175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6963   -9.2675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6312   -6.9693    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9779  -10.3883    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7802   -6.6071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1752   -5.3559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9818   -9.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9976   -9.8804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  1 15  1  1  0  0  0
  4  2  1  0  0  0  0
  9  2  1  0  0  0  0
  2 25  1  6  0  0  0
  8  3  1  0  0  0  0
  5  3  1  0  0  0  0
  4  3  1  0  0  0  0
  3 27  1  6  0  0  0
 11  4  1  0  0  0  0
  4 26  1  1  0  0  0
 12  5  1  0  0  0  0
  5 16  1  1  0  0  0
 17  5  1  0  0  0  0
 10  6  1  0  0  0  0
 14  6  1  0  0  0  0
  6 28  1  6  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 13 11  1  0  0  0  0
 20 12  1  0  0  0  0
 13 12  1  0  0  0  0
 19 14  1  0  0  0  0
 14 21  1  6  0  0  0
 23 17  1  0  0  0  0
 19 18  1  0  0  0  0
 22 18  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 12 29  1  1  0  0  0
 30 22  2  0  0  0  0
 31 22  1  0  0  0  0
 24 32  1  6  0  0  0
 11 33  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000518

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1

> <INCHI_KEY>
RUDATBOHQWOJDD-BSWAIDMHSA-N

> <FORMULA>
C24H40O4

> <MOLECULAR_WEIGHT>
392.572

> <EXACT_MASS>
392.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
46.34522129188202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.7133055236666674

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296339908541825

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.595945733487658

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5356636301705279

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
109.27379999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000518
     RDKit          3D
Chenodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
    3.9687    1.7666   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8618    0.2701   -0.3380 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9494   -0.3652   -1.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3406   -0.0316   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7437   -0.4122    0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9708   -1.0154    1.3442 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0104   -0.0987    1.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -0.2422   -0.9008 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5885   -1.7702   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649   -2.1924   -0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3810   -0.9554   -0.6534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9225   -0.9087    0.1001 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5782    0.3982   -0.3012 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6813    1.5813   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7053    1.4325   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3482    0.1255   -0.1422 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4456   -0.0403    1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9340    0.5936    0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8119    1.4667    1.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8155    1.2321   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0794    1.6660   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7608    0.6033    0.7010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0252    0.3941    0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436   -0.6704    0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843   -0.6998    0.7039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2424   -1.8223   -0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7874   -2.0124   -0.4693 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5276   -2.0228   -1.8601 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0014    2.1383   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6176    2.2557    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3914    2.1962   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0178   -0.0091    0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376   -0.0423   -2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -1.4857   -1.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162    1.0294   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0184   -0.6221   -1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3821    0.8182    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    0.0707   -1.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697   -1.9872    0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939   -2.2547   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8812   -2.9373   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -2.7152    0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1776   -0.7279   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7962   -0.9943    1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733    0.3346   -1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1485    2.4487   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6381    1.8897    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8185    1.5467   -1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110    2.2542   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3204    0.4629    1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5487    0.4329    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4231   -1.1012    1.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    1.5172    2.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5617    2.5169    1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0434    1.0025    2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3483    2.1343   -1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0257    0.5118   -1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8136    2.5628    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7316    2.1124   -0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0472    1.0619    1.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4816   -0.3093    0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5640   -1.4490    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2735   -1.0404    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -1.0158    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8126   -1.6492   -1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6643   -2.7510    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232   -3.0209   -0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877   -1.4553   -2.3389 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
 16 17  1  1
 13 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 16  8  1  0
 25 18  1  0
 16 11  1  0
 27 12  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 13 45  1  6
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 19 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  1
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  1
 26 65  1  0
 26 66  1  0
 27 67  1  1
 28 68  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      22.633 -14.241   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.633 -15.749   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.966 -15.749   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.329 -16.488   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.633 -16.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.097 -13.763   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.329 -13.459   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.966 -14.241   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.097 -16.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.967 -15.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.329 -18.053   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.633 -18.053   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.966 -18.821   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.097 -12.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.633 -12.661   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.633 -14.980   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.329 -15.749   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.778 -12.140   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.459 -11.386   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.329 -18.821   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.691 -10.979   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.097 -11.343   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.981 -16.500   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.981 -18.040   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      22.633 -17.299   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      21.343 -14.966   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      19.966 -17.299   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      25.445 -13.009   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      18.625 -19.391   0.000  0.00  0.00           H+0
HETATM   30  O   UNK     0      29.456 -12.333   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      28.327  -9.998   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      14.899 -18.573   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      22.396 -18.443   0.000  0.00  0.00           O+0
CONECT    1    2    6    7   15                                             
CONECT    2    1    4    9   25                                             
CONECT    3    8    5    4   27                                             
CONECT    4    2    3   11   26                                             
CONECT    5    3   12   16   17                                             
CONECT    6    1   10   14   28                                             
CONECT    7    1    8                                                       
CONECT    8    3    7                                                       
CONECT    9    2   10                                                       
CONECT   10    6    9                                                       
CONECT   11    4   13   33                                                  
CONECT   12    5   20   13   29                                             
CONECT   13   11   12                                                       
CONECT   14    6   19   21                                                  
CONECT   15    1                                                            
CONECT   16    5                                                            
CONECT   17    5   23                                                       
CONECT   18   19   22                                                       
CONECT   19   14   18                                                       
CONECT   20   12   24                                                       
CONECT   21   14                                                            
CONECT   22   18   30   31                                                  
CONECT   23   17   24                                                       
CONECT   24   20   23   32                                                  
CONECT   25    2                                                            
CONECT   26    4                                                            
CONECT   27    3                                                            
CONECT   28    6                                                            
CONECT   29   12                                                            
CONECT   30   22                                                            
CONECT   31   22                                                            
CONECT   32   24                                                            
CONECT   33   11                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000518
HETATM    1  C1  UNL     1       3.969   1.767  -0.423  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.862   0.270  -0.338  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.949  -0.365  -1.166  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.341  -0.032  -0.771  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.744  -0.412   0.581  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.971  -1.015   1.344  1.00  0.00           O  
HETATM    7  O2  UNL     1       8.010  -0.099   1.029  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.561  -0.242  -0.901  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.589  -1.770  -0.753  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.165  -2.192  -0.474  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.381  -0.955  -0.653  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.922  -0.909   0.100  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.578   0.398  -0.301  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.681   1.581  -0.044  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.705   1.433  -0.550  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.348   0.126  -0.142  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.446  -0.040   1.338  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.934   0.594   0.296  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.812   1.467   1.505  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.815   1.232  -0.751  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.079   1.666  -0.082  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.761   0.603   0.701  1.00  0.00           C  
HETATM   23  O3  UNL     1      -7.025   0.394   0.089  1.00  0.00           O  
HETATM   24  C21 UNL     1      -5.044  -0.670   0.879  1.00  0.00           C  
HETATM   25  C22 UNL     1      -3.584  -0.700   0.704  1.00  0.00           C  
HETATM   26  C23 UNL     1      -3.242  -1.822  -0.289  1.00  0.00           C  
HETATM   27  C24 UNL     1      -1.787  -2.012  -0.469  1.00  0.00           C  
HETATM   28  O4  UNL     1      -1.528  -2.023  -1.860  1.00  0.00           O  
HETATM   29  H1  UNL     1       5.001   2.138  -0.554  1.00  0.00           H  
HETATM   30  H2  UNL     1       3.618   2.256   0.530  1.00  0.00           H  
HETATM   31  H3  UNL     1       3.391   2.196  -1.279  1.00  0.00           H  
HETATM   32  H4  UNL     1       4.018  -0.009   0.708  1.00  0.00           H  
HETATM   33  H5  UNL     1       4.738  -0.042  -2.228  1.00  0.00           H  
HETATM   34  H6  UNL     1       4.825  -1.486  -1.209  1.00  0.00           H  
HETATM   35  H7  UNL     1       6.616   1.029  -1.013  1.00  0.00           H  
HETATM   36  H8  UNL     1       7.018  -0.622  -1.468  1.00  0.00           H  
HETATM   37  H9  UNL     1       8.382   0.818   1.142  1.00  0.00           H  
HETATM   38  H10 UNL     1       2.474   0.071  -1.940  1.00  0.00           H  
HETATM   39  H11 UNL     1       3.170  -1.987   0.161  1.00  0.00           H  
HETATM   40  H12 UNL     1       2.994  -2.255  -1.664  1.00  0.00           H  
HETATM   41  H13 UNL     1       0.881  -2.937  -1.273  1.00  0.00           H  
HETATM   42  H14 UNL     1       1.039  -2.715   0.478  1.00  0.00           H  
HETATM   43  H15 UNL     1       0.178  -0.728  -1.706  1.00  0.00           H  
HETATM   44  H16 UNL     1      -0.796  -0.994   1.194  1.00  0.00           H  
HETATM   45  H17 UNL     1      -1.673   0.335  -1.427  1.00  0.00           H  
HETATM   46  H18 UNL     1      -1.148   2.449  -0.591  1.00  0.00           H  
HETATM   47  H19 UNL     1      -0.638   1.890   1.011  1.00  0.00           H  
HETATM   48  H20 UNL     1       0.819   1.547  -1.643  1.00  0.00           H  
HETATM   49  H21 UNL     1       1.311   2.254  -0.095  1.00  0.00           H  
HETATM   50  H22 UNL     1       2.320   0.463   1.791  1.00  0.00           H  
HETATM   51  H23 UNL     1       0.549   0.433   1.804  1.00  0.00           H  
HETATM   52  H24 UNL     1       1.423  -1.101   1.665  1.00  0.00           H  
HETATM   53  H25 UNL     1      -3.734   1.517   2.121  1.00  0.00           H  
HETATM   54  H26 UNL     1      -2.562   2.517   1.251  1.00  0.00           H  
HETATM   55  H27 UNL     1      -2.043   1.003   2.188  1.00  0.00           H  
HETATM   56  H28 UNL     1      -3.348   2.134  -1.210  1.00  0.00           H  
HETATM   57  H29 UNL     1      -4.026   0.512  -1.566  1.00  0.00           H  
HETATM   58  H30 UNL     1      -4.814   2.563   0.553  1.00  0.00           H  
HETATM   59  H31 UNL     1      -5.732   2.112  -0.892  1.00  0.00           H  
HETATM   60  H32 UNL     1      -6.047   1.062   1.696  1.00  0.00           H  
HETATM   61  H33 UNL     1      -7.482  -0.309   0.652  1.00  0.00           H  
HETATM   62  H34 UNL     1      -5.564  -1.449   0.240  1.00  0.00           H  
HETATM   63  H35 UNL     1      -5.274  -1.040   1.926  1.00  0.00           H  
HETATM   64  H36 UNL     1      -3.042  -1.016   1.647  1.00  0.00           H  
HETATM   65  H37 UNL     1      -3.813  -1.649  -1.219  1.00  0.00           H  
HETATM   66  H38 UNL     1      -3.664  -2.751   0.172  1.00  0.00           H  
HETATM   67  H39 UNL     1      -1.423  -3.021  -0.119  1.00  0.00           H  
HETATM   68  H40 UNL     1      -2.188  -1.455  -2.339  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    8   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6    6    7
CONECT    7   37
CONECT    8    9   16   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   16   43
CONECT   12   13   27   44
CONECT   13   14   18   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17
CONECT   17   50   51   52
CONECT   18   19   20   25
CONECT   19   53   54   55
CONECT   20   21   56   57
CONECT   21   22   58   59
CONECT   22   23   24   60
CONECT   23   61
CONECT   24   25   62   63
CONECT   25   26   64
CONECT   26   27   65   66
CONECT   27   28   67
CONECT   28   68
END

HMDB0000518
     RDKit          3D
Chenodeoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
    3.9687    1.7666   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8618    0.2701   -0.3380 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9494   -0.3652   -1.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3406   -0.0316   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7437   -0.4122    0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9708   -1.0154    1.3442 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0104   -0.0987    1.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -0.2422   -0.9008 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5885   -1.7702   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649   -2.1924   -0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3810   -0.9554   -0.6534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9225   -0.9087    0.1001 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5782    0.3982   -0.3012 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6813    1.5813   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7053    1.4325   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3482    0.1255   -0.1422 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4456   -0.0403    1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9340    0.5936    0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8119    1.4667    1.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8155    1.2321   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0794    1.6660   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7608    0.6033    0.7010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0252    0.3941    0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436   -0.6704    0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843   -0.6998    0.7039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2424   -1.8223   -0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7874   -2.0124   -0.4693 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5276   -2.0228   -1.8601 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0014    2.1383   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6176    2.2557    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3914    2.1962   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0178   -0.0091    0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376   -0.0423   -2.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -1.4857   -1.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162    1.0294   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0184   -0.6221   -1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3821    0.8182    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735    0.0707   -1.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697   -1.9872    0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939   -2.2547   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8812   -2.9373   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -2.7152    0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1776   -0.7279   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7962   -0.9943    1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733    0.3346   -1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1485    2.4487   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6381    1.8897    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8185    1.5467   -1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110    2.2542   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3204    0.4629    1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5487    0.4329    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4231   -1.1012    1.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    1.5172    2.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5617    2.5169    1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0434    1.0025    2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3483    2.1343   -1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0257    0.5118   -1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8136    2.5628    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7316    2.1124   -0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0472    1.0619    1.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4816   -0.3093    0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5640   -1.4490    0.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2735   -1.0404    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -1.0158    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8126   -1.6492   -1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6643   -2.7510    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232   -3.0209   -0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877   -1.4553   -2.3389 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
 16 17  1  1
 13 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 16  8  1  0
 25 18  1  0
 16 11  1  0
 27 12  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 13 45  1  6
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 19 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  1
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  1
 26 65  1  0
 26 66  1  0
 27 67  1  1
 28 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3alpha,7alpha-Dihydroxy-5beta-cholanic acid	ChEBI
7alpha-Hydroxylithocholic acid	ChEBI
Anthropodeoxycholic acid	ChEBI
Anthropodesoxycholic acid	ChEBI
CDCA	ChEBI
Chenic acid	ChEBI
Chenix	ChEBI
Chenodiol	ChEBI
Gallodesoxycholic acid	ChEBI
3a,7a-Dihydroxy-5b-cholanate	Generator
3a,7a-Dihydroxy-5b-cholanic acid	Generator
3alpha,7alpha-Dihydroxy-5beta-cholanate	Generator
3Α,7α-dihydroxy-5β-cholanate	Generator
3Α,7α-dihydroxy-5β-cholanic acid	Generator
7a-Hydroxylithocholate	Generator
7a-Hydroxylithocholic acid	Generator
7alpha-Hydroxylithocholate	Generator
7Α-hydroxylithocholate	Generator
7Α-hydroxylithocholic acid	Generator
Anthropodeoxycholate	Generator
Anthropodesoxycholate	Generator
Chenate	Generator
Gallodesoxycholate	Generator
Chenodeoxycholate	Generator
(+)-Chenodeoxycholate	HMDB
(+)-Chenodeoxycholic acid	HMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oate	HMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oic acid	HMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanate	HMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanic acid	HMDB
3a,7a-Dihydroxy-5b-cholan-24-Oate	HMDB
3a,7a-Dihydroxy-5b-cholan-24-Oic acid	HMDB
7a-Hydroxy-desoxycholsaeure	HMDB
Chenodesoxycholsaeure	HMDB
Acid, chenique	HMDB
Chenofalk	HMDB
Chenophalk	HMDB
Acid, chenodeoxycholic	HMDB
Chenodeoxycholate, sodium	HMDB
Quenocol	HMDB
Solvay brand OF chenodeoxycholic acid	HMDB
Antigen brand OF chenodeoxycholic acid	HMDB
Falk brand OF chenodeoxycholic acid	HMDB
Quenobilan	HMDB
Sodium chenodeoxycholate	HMDB
Tramedico brand OF chenodeoxycholic acid	HMDB
Zambon brand OF chenodeoxycholic acid	HMDB
Acid, chenic	HMDB
Acid, gallodesoxycholic	HMDB
Chenique acid	HMDB
Estedi brand OF chenodeoxycholic acid	HMDB
Henohol	HMDB

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

IUPAC Name

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

CAS Registry Number

474-25-9

SMILES

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

InChI Identifier

InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1

InChI Key

RUDATBOHQWOJDD-BSWAIDMHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:16755 )
dihydroxy-5beta-cholanic acid (CHEBI:16755 )
C24 bile acids, alcohols, and derivatives (C02528 )
Cholane and derivatives (C02528 )
C24 bile acids, alcohols, and derivatives (LMST04010032 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Biliary atresia (HMDB: HMDB0000518)

Gastrointestinal disorder

Chronic diarrhea (PMID: 19900947)

Primary biliary cirrhosis (HMDB: HMDB0000518)
Cystic fibrosis (HMDB: HMDB0000518)
Cirrhosis (PMID: 1112456)
Jaundice (PMID: 1112456)
Chronic hepatitis (PMID: 1112456)

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Depression (PMID: 35445772)

Alzheimer's Disease (PMID: 30337151)

Cancer

Colorectal cancer (PMID: 21724466)

Disposition

Biological location

Biofluid or Excreta

Non-excretory biofluid

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

Excreta

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

Cellular substructure

Extracellular (HMDB: HMDB0000518)

Organ

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000518)

Fibroblasts (HMDB: HMDB0000518)

Tissue substructure

Hepatic tissue (HMDB: HMDB0000518)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000518)

Source

Endogenous

Endogenous (HMDB: HMDB0000518)

Exogenous

Food

Food (HMDB: HMDB0000518)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Bile Acid Biosynthesis (HMDB: HMDB0000518)

bile acid biosynthesis (HMDB: HMDB0000518)

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0000314)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0000318)
Familial Hypercholanemia (FHCA) (PathBank: SMP0000317)
Zellweger Syndrome (PathBank: SMP0000316)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0000315)
27-Hydroxylase Deficiency (PathBank: SMP0000720)

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000518)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000518)

Cellular process

Cell signaling (HMDB: HMDB0000518)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 - 167 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.09 mg/mL	Not Available
LogP	4.15	SANGSTER (1993)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	201.513	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000197

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.01	ALOGPS
logP	3.71	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.6	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.27 m³·mol⁻¹	ChemAxon
Polarizability	46.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	189.58	31661259
DarkChem	[M-H]-	187.634	31661259
AllCCS	[M+H]+	200.81	32859911
AllCCS	[M-H]-	198.892	32859911
DeepCCS	[M-2H]-	235.942	30932474
DeepCCS	[M+Na]+	209.905	30932474
AllCCS	[M+H]+	200.8	32859911
AllCCS	[M+H-H2O]+	198.7	32859911
AllCCS	[M+NH4]+	202.8	32859911
AllCCS	[M+Na]+	203.3	32859911
AllCCS	[M-H]-	198.9	32859911
AllCCS	[M+Na-2H]-	200.2	32859911
AllCCS	[M+HCOO]-	201.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chenodeoxycholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3820.1	Standard polar	33892256
Chenodeoxycholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3330.9	Standard non polar	33892256
Chenodeoxycholic acid	[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O	3473.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chenodeoxycholic acid,1TMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3313.4	Semi standard non polar	33892256
Chenodeoxycholic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3372.3	Semi standard non polar	33892256
Chenodeoxycholic acid,1TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3313.4	Semi standard non polar	33892256
Chenodeoxycholic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3232.6	Semi standard non polar	33892256
Chenodeoxycholic acid,2TMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3259.4	Semi standard non polar	33892256
Chenodeoxycholic acid,2TMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3321.5	Semi standard non polar	33892256
Chenodeoxycholic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3235.5	Semi standard non polar	33892256
Chenodeoxycholic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3530.1	Semi standard non polar	33892256
Chenodeoxycholic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3592.0	Semi standard non polar	33892256
Chenodeoxycholic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3577.3	Semi standard non polar	33892256
Chenodeoxycholic acid,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3702.6	Semi standard non polar	33892256
Chenodeoxycholic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3698.7	Semi standard non polar	33892256
Chenodeoxycholic acid,2TBDMS,isomer #3	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	3813.9	Semi standard non polar	33892256
Chenodeoxycholic acid,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3915.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Chenodeoxycholic acid GC-MS (3 TMS)	splash10-0a6u-3920000000-ce93b24c6e2568b6087d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chenodeoxycholic acid GC-MS (Non-derivatized)	splash10-0a6u-3920000000-ce93b24c6e2568b6087d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01rt-0419000000-6a92f910581240163a99	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1110390000-7a6c62344d1371b74081	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-0a4i-0009000000-82ed6dc62b49ac0340e6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-01pa-2930000000-64edc819ad56b842cdba	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-053r-6900000000-c97325e1ca9bcff75af1	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid LC-ESI-IT , negative-QTOF	splash10-0002-0009000000-ad2d2440db7f3f1c8a2e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 20V, Negative-QTOF	splash10-0006-0009000000-2df562379077bf0f4b2a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 40V, Negative-QTOF	splash10-0006-0009000000-ff13f6ad8405e3969b6c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 20V, Negative-QTOF	splash10-0006-0009000000-1af3ba6ee17285da06a2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-5409557fb9a76a8a8e74	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 40V, Negative-QTOF	splash10-0006-0009000000-c77d97d0dfe48497b263	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 30V, Negative-QTOF	splash10-0006-0009000000-d38671ccaaa16ac6d1f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 40V, Negative-QTOF	splash10-0596-0529000000-1ed436cc96fa78f90b88	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-25ba2afe78d7d8070765	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 20V, Negative-QTOF	splash10-0006-0019000000-c31d129de7de9df05167	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 20V, Negative-QTOF	splash10-0006-0009000000-fc161813afdb6d319d8d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 40V, Negative-QTOF	splash10-0006-0009000000-ee319e0cbd9987920deb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-858f2baceacfba406468	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 10V, Positive-QTOF	splash10-056r-0009000000-997e61e986e67265241c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 20V, Positive-QTOF	splash10-056r-0009000000-81134947694f847d1c65	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 40V, Positive-QTOF	splash10-02t9-1219000000-6a0ddebebacac090c27e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-efdaad69eee0ae934dd5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 20V, Negative-QTOF	splash10-006x-1009000000-15b4edab9d05e4c3693a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-9291e69db3a3c47ecd97	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 10V, Negative-QTOF	splash10-0006-0009000000-7631731446db77938069	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 20V, Negative-QTOF	splash10-006x-0009000000-39e7e555dc6b36ada2af	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid 40V, Negative-QTOF	splash10-000i-1009000000-351c21e3dab693818b22	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Urine

Tissue Locations

Fibroblasts
Liver

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bile	Detected and Quantified	5530 (5400-5660) uM	Adult (>18 years old)	Both	Normal	16548228	details
Blood	Detected and Quantified	0.98 +/- 0.66 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	1.8 +/- 0.4 uM	Newborn (0-30 days old)	Both	Normal	16553252	details
Blood	Detected and Quantified	0.2(0.2-0.2) uM	Infant (0-1 year old)	Both	Normal	27163928	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	1.35 +/- 0.27 uM	Adult (>18 years old)	Both	Normal	15185309	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	21458633	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23384618	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected and Quantified	54.8 +/- 72.07 nmol/g dry feces	Not Specified	Not Specified	Normal	22664055	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	22.0 (3.3-46.3) uM	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Blood	Detected and Quantified	11.0 (0.8-28.0) uM	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Blood	Detected and Quantified	7.4 +/- 2.5 uM	Newborn (0-30 days old)	Both	Extrahepatic biliary atresia (EHBA)	16553252	details
Blood	Detected and Quantified	0.1(0.1-0.2) uM	Infant (0-1 year old)	Both	Severe acute malnutrition	27163928	details
Blood	Detected and Quantified	2.83 +/- 0.42 uM	Adult (>18 years old)	Both	Cystic fibrosis	15185309	details
Blood	Detected and Quantified	2.75 +/- 0.56 uM	Children (1-13 years old)	Both	Cystic fibrosis	15185309	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Liver cirrhosis	21458633	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	hepatocellular carcinoma	21458633	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	liver cirrhosis	23384618	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Recurrent Clostridium difficile infection	24284963	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Recurrent Clostridium difficile infection	24284963	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	24284963	details
Urine	Detected and Quantified	1.4 (0.14-2.9) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	1.1 (0.04-3.3) umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	2621422	details
Urine	Detected and Quantified	0.0092 +/- 0.013 umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	3944741	details

Associated Disorders and Diseases

Disease References

Cystic fibrosis
Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
Biliary atresia
Gustafsson J, Alvelius G, Bjorkhem I, Nemeth A: Bile acid metabolism in extrahepatic biliary atresia: lithocholic acid in stored dried blood collected at neonatal screening. Ups J Med Sci. 2006;111(1):131-6. [PubMed:16553252 ] Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. [PubMed:3944741 ]
Cirrhosis
Cao H, Huang H, Xu W, Chen D, Yu J, Li J, Li L: Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal Chim Acta. 2011 Apr 8;691(1-2):68-75. doi: 10.1016/j.aca.2011.02.038. Epub 2011 Feb 23. [PubMed:21458633 ] Huang HJ, Zhang AY, Cao HC, Lu HF, Wang BH, Xie Q, Xu W, Li LJ: Metabolomic analyses of faeces reveals malabsorption in cirrhotic patients. Dig Liver Dis. 2013 Aug;45(8):677-82. doi: 10.1016/j.dld.2013.01.001. Epub 2013 Feb 4. [PubMed:23384618 ]
Hepatocellular carcinoma
Cao H, Huang H, Xu W, Chen D, Yu J, Li J, Li L: Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal Chim Acta. 2011 Apr 8;691(1-2):68-75. doi: 10.1016/j.aca.2011.02.038. Epub 2011 Feb 23. [PubMed:21458633 ]
Primary biliary cirrhosis
Batta AK, Arora R, Salen G, Tint GS, Eskreis D, Katz S: Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment. J Lipid Res. 1989 Dec;30(12):1953-62. [PubMed:2621422 ]

Associated OMIM IDs

219700 (Cystic fibrosis)
210500 (Biliary atresia)
114550 (Hepatocellular carcinoma)
109720 (Primary biliary cirrhosis)

External Links

DrugBank ID

DB06777

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022087

KNApSAcK ID

Not Available

Chemspider ID

9728

KEGG Compound ID

C02528

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chenodiol

METLIN ID

207

PubChem Compound

10133

PDB ID

Not Available

ChEBI ID

16755

Food Biomarker Ontology

Not Available

VMH ID

C02528

MarkerDB ID

MDB00000180

Good Scents ID

Not Available

References

Synthesis Reference

Sato, Yoshio; Ikekawa, Nobuo. Preparation of chenodeoxycholic acid. Journal of Organic Chemistry (1959), 24 1367-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10. [PubMed:16548228 ]
Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
Fiorucci S, Antonelli E, Morelli A: Nitric oxide and portal hypertension: a nitric oxide-releasing derivative of ursodeoxycholic acid that selectively releases nitric oxide in the liver. Dig Liver Dis. 2003 May;35 Suppl 2:S61-9. [PubMed:12846445 ]
Meyers RL, Book LS, O'Gorman MA, Jackson WD, Black RE, Johnson DG, Matlak ME: High-dose steroids, ursodeoxycholic acid, and chronic intravenous antibiotics improve bile flow after Kasai procedure in infants with biliary atresia. J Pediatr Surg. 2003 Mar;38(3):406-11. [PubMed:12632357 ]
Soderdahl G, Nowak G, Duraj F, Wang FH, Einarsson C, Ericzon BG: Ursodeoxycholic acid increased bile flow and affects bile composition in the early postoperative phase following liver transplantation. Transpl Int. 1998;11 Suppl 1:S231-8. [PubMed:9664985 ]
Nobilis M, Pour M, Kunes J, Kopecky J, Kvetina J, Svoboda Z, Sladkova K, Vortel J: High-performance liquid chromatographic determination of ursodeoxycholic acid after solid phase extraction of blood serum and detection-oriented derivatization. J Pharm Biomed Anal. 2001 Mar;24(5-6):937-46. [PubMed:11248487 ]
Dohmen K, Mizuta T, Nakamuta M, Shimohashi N, Ishibashi H, Yamamoto K: Fenofibrate for patients with asymptomatic primary biliary cirrhosis. World J Gastroenterol. 2004 Mar 15;10(6):894-8. [PubMed:15040040 ]
Lupton JR, Steinbach G, Chang WC, O'Brien BC, Wiese S, Stoltzfus CL, Glober GA, Wargovich MJ, McPherson RS, Winn RJ: Calcium supplementation modifies the relative amounts of bile acids in bile and affects key aspects of human colon physiology. J Nutr. 1996 May;126(5):1421-8. [PubMed:8618139 ]
Hillaire S, Ballet F, Franco D, Setchell KD, Poupon R: Effects of ursodeoxycholic acid and chenodeoxycholic acid on human hepatocytes in primary culture. Hepatology. 1995 Jul;22(1):82-7. [PubMed:7601437 ]
Kitani K, Kanai S, Ivy GO, Carrillo MC: Pharmacological modifications of endogenous antioxidant enzymes with special reference to the effects of deprenyl: a possible antioxidant strategy. Mech Ageing Dev. 1999 Nov;111(2-3):211-21. [PubMed:10656538 ]
Reyes H, Sjovall J: Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy. Ann Med. 2000 Mar;32(2):94-106. [PubMed:10766400 ]
Stark M, Jornvall H, Johansson J: Isolation and characterization of hydrophobic polypeptides in human bile. Eur J Biochem. 1999 Nov;266(1):209-14. [PubMed:10542066 ]
Hofmann AF: The continuing importance of bile acids in liver and intestinal disease. Arch Intern Med. 1999 Dec 13-27;159(22):2647-58. [PubMed:10597755 ]
Morton DH, Salen G, Batta AK, Shefer S, Tint GS, Belchis D, Shneider B, Puffenberger E, Bull L, Knisely AS: Abnormal hepatic sinusoidal bile acid transport in an Amish kindred is not linked to FIC1 and is improved by ursodiol. Gastroenterology. 2000 Jul;119(1):188-95. [PubMed:10889168 ]
Virovic L, Supanc V, Duvnjak M: [Primary sclerosing cholangitis--diagnosis and therapy]. Acta Med Croatica. 2003;57(3):207-19. [PubMed:14582467 ]
Gatzen M, Pausch J: [Treatment of cholestatic liver diseases]. Med Klin (Munich). 2002 Mar 15;97(3):152-9. [PubMed:11957790 ]
Eriksson LS, Olsson R, Glauman H, Prytz H, Befrits R, Ryden BO, Einarsson K, Lindgren S, Wallerstedt S, Weden M: Ursodeoxycholic acid treatment in patients with primary biliary cirrhosis. A Swedish multicentre, double-blind, randomized controlled study. Scand J Gastroenterol. 1997 Feb;32(2):179-86. [PubMed:9051880 ]
Lindblad A, Glaumann H, Strandvik B: A two-year prospective study of the effect of ursodeoxycholic acid on urinary bile acid excretion and liver morphology in cystic fibrosis-associated liver disease. Hepatology. 1998 Jan;27(1):166-74. [PubMed:9425933 ]
Kowdley KV: Ursodeoxycholic acid therapy in hepatobiliary disease. Am J Med. 2000 Apr 15;108(6):481-6. [PubMed:10781781 ]
Azer SA, Coverdale SA, Byth K, Farrell GC, Stacey NH: Sequential changes in serum levels of individual bile acids in patients with chronic cholestatic liver disease. J Gastroenterol Hepatol. 1996 Mar;11(3):208-15. [PubMed:8742915 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C1

General function:: Involved in oxidoreductase activity
Specific function:: Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:: AKR1C1
Uniprot ID:: Q04828
Molecular weight:: 36788.02

Enzyme Details

2. Aldo-keto reductase family 1 member C2

General function:: Involved in oxidoreductase activity
Specific function:: Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:: AKR1C2
Uniprot ID:: P52895
Molecular weight:: 15747.91

Enzyme Details

3. 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

Chenodeoxycholic acid + Coenzyme A → Chenodeoxycholoyl-CoA + Water	details

Enzyme Details

4. 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

Chenodeoxycholoyl-CoA + Adenosine monophosphate + Pyrophosphate → Chenodeoxycholic acid + Coenzyme A + Adenosine triphosphate	details

Enzyme Details

5. Gastrotropin

General function:: Involved in binding
Specific function:: Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:: FABP6
Uniprot ID:: P51161
Molecular weight:: 14371.2

References

Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B3

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:: SLCO1B3
Uniprot ID:: Q9NPD5
Molecular weight:: 77402.2

Enzyme Details

2. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]

Enzyme Details

3. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

Enzyme Details

4. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

Enzyme Details

5. Ileal sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:: SLC10A2
Uniprot ID:: Q12908
Molecular weight:: 37697.4

References

Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]

Enzyme Details

6. Sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:: SLC10A1
Uniprot ID:: Q14973
Molecular weight:: 38118.64

Enzyme Details

7. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

Enzyme Details

8. Solute carrier organic anion transporter family member 4A1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:: SLCO4A1
Uniprot ID:: Q96BD0
Molecular weight:: 77192.5

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Showing metabocard for Chenodeoxycholic acid (HMDB0000518)

MOL for HMDB0000518 (Chenodeoxycholic acid)

3D MOL for HMDB0000518 (Chenodeoxycholic acid)

3D SDF for HMDB0000518 (Chenodeoxycholic acid)

3D-SDF for HMDB0000518 (Chenodeoxycholic acid)

PDB for HMDB0000518 (Chenodeoxycholic acid)

3D PDB for HMDB0000518 (Chenodeoxycholic acid)

SMILES for HMDB0000518 (Chenodeoxycholic acid)

INCHI for HMDB0000518 (Chenodeoxycholic acid)

Structure for HMDB0000518 (Chenodeoxycholic acid)

3D Structure for HMDB0000518 (Chenodeoxycholic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

References

Transporters

References

References