MiMeDB: Showing metabocard for Chenodeoxycholic acid (MMDBc0000113)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:36:21 UTC

Update Date

2024-10-10 23:40:33 UTC

Metabolite ID

MMDBc0000113

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
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 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
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 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>
MMDBc0000113

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₂₄H₄₀O₄

Average Mass

392.572

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0a6u-3920000000-ce93b24c6e2568b6087d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a6u-3920000000-ce93b24c6e2568b6087d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01rt-0419000000-6a92f910581240163a99	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1110390000-7a6c62344d1371b74081	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_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 (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_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0a4i-0009000000-82ed6dc62b49ac0340e6	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-01pa-2930000000-64edc819ad56b842cdba	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-053r-6900000000-c97325e1ca9bcff75af1	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0002-0009000000-ad2d2440db7f3f1c8a2e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-2df562379077bf0f4b2a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0009000000-ff13f6ad8405e3969b6c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-1af3ba6ee17285da06a2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-5409557fb9a76a8a8e74	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0009000000-c77d97d0dfe48497b263	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-0009000000-d38671ccaaa16ac6d1f1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0596-0529000000-1ed436cc96fa78f90b88	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-25ba2afe78d7d8070765	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0019000000-c31d129de7de9df05167	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-fc161813afdb6d319d8d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0009000000-ee319e0cbd9987920deb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-858f2baceacfba406468	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0009000000-997e61e986e67265241c	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0009000000-81134947694f847d1c65	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02t9-1219000000-6a0ddebebacac090c27e	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-efdaad69eee0ae934dd5	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-1009000000-15b4edab9d05e4c3693a	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-9291e69db3a3c47ecd97	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-7631731446db77938069	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0009000000-39e7e555dc6b36ada2af	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1009000000-351c21e3dab693818b22	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Fibroblasts
Liver
Urine

Tissue Locations

Fibroblasts
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192053	Aldo-keto reductase family 1 member C1	Unknown	Q04828	Homo sapiens
MMDBp0192054	Aldo-keto reductase family 1 member C2	Unknown	P52895	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
MMDBp0192658	Acyl-coenzyme A thioesterase 8	Enzyme	O14734	Homo sapiens
MMDBp0193395	Canalicular multispecific organic anion transporter 2	Transporter	O15438	Homo sapiens
MMDBp0193400	Bile salt export pump	Transporter	O95342	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
MMDBp0193865	Solute carrier organic anion transporter family member 4A1	Transporter	Q96BD0	Homo sapiens
MMDBp0195864	Gastrotropin	Unknown	P51161	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0002647	Chenodeoxycholic acid	Chenodeoxycholoyl-CoA	solute carrier family 27 (fatty acid transporter), member 2	VMH; KEGG	30371894
MMDBr0002648	Chenodeoxycholic acid	Chenodeoxycholoyl-CoA	solute carrier family 27 (fatty acid transporter), member 5	VMH; KEGG	30371894
MMDBr0004098	Chenodeoxycholoyl-CoA	Chenodeoxycholic acid	acyl-CoA thioesterase 1	VMH; KEGG	30371894
MMDBr0004099	Chenodeoxycholoyl-CoA	Chenodeoxycholic acid	acyl-CoA thioesterase 2	VMH	10817395 10944470 11454857 11673457
MMDBr0004100	Chenodeoxycholoyl-CoA	Chenodeoxycholic acid	acyl-CoA thioesterase 4	VMH	10817395 10944470 11454857 11673457
MMDBr0006120	Chenodeoxycholic acid	Nutriacholic acid	Not Available	VMH	30371894
MMDBr0009565	Sulfochenodeoxycholate	Chenodeoxycholic acid	steroid sulfatase (microsomal), isozyme S	VMH	30371894
MMDBr0012376	Chenodeoxycholic acid	3a,6a,7b-Trihydroxy-5b-cholanoic acid	cytochrome P450, family 3, subfamily A, polypeptide 4	VMH	30371894
MMDBr0012622	Chenodeoxycholic acid glycine conjugate	Chenodeoxycholic acid	Not Available	VMH	30371894
MMDBr0012624	Taurochenodesoxycholic acid	Chenodeoxycholic acid	Not Available	VMH	30371894
MMDBr0012643	Chenodeoxycholic acid	Chenodeoxycholoyl-CoA	Not Available	VMH	30371894

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
Cystic fibrosis		Association	Human Blood	HMDB	15185309
Primary biliary cirrhosis		Association	Human Urine	HMDB	2621422
Primary biliary cirrhosis	Slight Increase	Association	Human Blood	HMDB	2621422

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	117	Human ; Human mucosa; Human feces; Human saliva; Pig	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Bacteroidetes	59	Human feces; Human stool; Human ; Human urine; Human saliva; Human appendix biopsy	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	18	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Microbial culture; Metabolic reconstruction
Bacteria	Actinobacteria	50	Human ; Human feces; Human saliva; Human mucosa; Human stool	Microbial culture; Metabolic reconstruction
Bacteria	Fusobacteria	3	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Not Available	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

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	0.0092	0.013			umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	HMDB	3944741
Human Blood	Detected and Quantified	7.4	2.5			uM	Newborn (0-30 days old)	Both	Extrahepatic biliary atresia (EHBA)	HMDB	16553252
Human Blood	Detected and Quantified	2.75	0.56			uM	Children (1-13 years old)	Both	Cystic fibrosis	HMDB	15185309
Human Blood	Detected and Quantified	2.83	0.42			uM	Adult (>18 years old)	Both	Cystic fibrosis	HMDB	15185309
Human Urine	Detected and Quantified	1.1		0.04	3.3	umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	1.4		0.14	2.9	umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Blood	Detected and Quantified	11.0		0.8	28.0	uM	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Blood	Detected and Quantified	22.0		3.3	46.3	uM	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Blood	Detected and Quantified	0.2		0.2	0.2	uM	Infant (0-1 year old)	Both	Normal	HMDB	27163928
Human Blood	Detected and Quantified	1.35	0.27			uM	Adult (>18 years old)	Both	Normal	HMDB	15185309
Human Blood	Detected and Quantified	1.8	0.4			uM	Newborn (0-30 days old)	Both	Normal	HMDB	16553252
Human Feces	Detected and Quantified	54.8	72.07			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Bile	Detected and Quantified	5530		5400	5660	uM	Adult (>18 years old)	Both	Normal	HMDB	16548228
Human Blood	Detected and Quantified	0.98	0.66			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Fibroblasts	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 Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	21458633
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23384618
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	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

HMDB0000518

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

References

Synthesis Reference

Not Available

General References

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 ]
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. doi: 10.1093/jn/126.5.1421. [PubMed:8618139 ]
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. doi: 10.1111/j.1440-1746.1996.tb00064.x. [PubMed:8742915 ]
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. doi: 10.3109/00365529709000190. [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. doi: 10.1002/hep.510270126. [PubMed:9425933 ]
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. doi: 10.1007/s001470050467. [PubMed:9664985 ]
Stark M, Jornvall H, Johansson J: Isolation and characterization of hydrophobic polypeptides in human bile. Eur J Biochem. 1999 Nov;266(1):209-14. doi: 10.1046/j.1432-1327.1999.00845.x. [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. doi: 10.1001/archinte.159.22.2647. [PubMed:10597755 ]
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. doi: 10.1016/s0047-6374(99)00065-2. [PubMed:10656538 ]
Reyes H, Sjovall J: Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy. Ann Med. 2000 Mar;32(2):94-106. doi: 10.3109/07853890009011758. [PubMed:10766400 ]
Kowdley KV: Ursodeoxycholic acid therapy in hepatobiliary disease. Am J Med. 2000 Apr 15;108(6):481-6. doi: 10.1016/s0002-9343(00)00318-1. [PubMed:10781781 ]
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. doi: 10.1053/gast.2000.8547. [PubMed:10889168 ]
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. doi: 10.1016/s0731-7085(00)00563-x. [PubMed:11248487 ]
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 ]
Gatzen M, Pausch J: [Treatment of cholestatic liver diseases]. Med Klin (Munich). 2002 Mar 15;97(3):152-9. doi: 10.1007/s00063-002-1139-7. [PubMed:11957790 ]
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 ]
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. doi: 10.1053/jpsu.2003.50069. [PubMed:12632357 ]
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. doi: 10.1016/s1590-8658(03)00053-7. [PubMed:12846445 ]
Virovic L, Supanc V, Duvnjak M: [Primary sclerosing cholangitis--diagnosis and therapy]. Acta Med Croatica. 2003;57(3):207-19. [PubMed:14582467 ]
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. doi: 10.3748/wjg.v10.i6.894. [PubMed:15040040 ]
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 ]

Showing metabocard for Chenodeoxycholic acid (MMDBc0000113)

MOL for #<Metabolite:0x00007fdb0cc08c00>

3D MOL for #<Metabolite:0x00007fdb0cc08c00>

3D SDF for #<Metabolite:0x00007fdb0cc08c00>

3D-SDF for #<Metabolite:0x00007fdb0cc08c00>

PDB for #<Metabolite:0x00007fdb0cc08c00>

3D PDB for #<Metabolite:0x00007fdb0cc08c00>

SMILES for #<Metabolite:0x00007fdb0cc08c00>

INCHI for #<Metabolite:0x00007fdb0cc08c00>

Structure for #<Metabolite:0x00007fdb0cc08c00>

3D Structure for #<Metabolite:0x00007fdb0cc08c00>