NP-MRD: Showing NP-Card for Chenodeoxycholic acid (NP0000980)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:41:55 UTC

NP-MRD ID

NP0000980

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chenodeoxycholic acid

Description

Chenodeoxycholic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on 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
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  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
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 10 42  1  0
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 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>
NP0000980

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

392.5720 Da

Monoisotopic Mass

392.29266 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Bos taurus domesticus	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	165 - 167 °C	Not Available
Boiling Point	547.15 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.09 mg/mL	Not Available
LogP	4.15	Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.

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

External Links

HMDB ID

HMDB0000518

DrugBank ID

DB06777

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chenodiol

METLIN ID

207

PubChem Compound

10133

PDB ID

Not Available

ChEBI ID

16755

Good Scents ID

rw1228061

References

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 ]
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 ]
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 ]
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Showing NP-Card for Chenodeoxycholic acid (NP0000980)

MOL for NP0000980 (Chenodeoxycholic acid)

3D MOL for NP0000980 (Chenodeoxycholic acid)

3D SDF for NP0000980 (Chenodeoxycholic acid)

3D-SDF for NP0000980 (Chenodeoxycholic acid)

PDB for NP0000980 (Chenodeoxycholic acid)

3D PDB for NP0000980 (Chenodeoxycholic acid)

SMILES for NP0000980 (Chenodeoxycholic acid)

INCHI for NP0000980 (Chenodeoxycholic acid)

Structure for NP0000980 (Chenodeoxycholic acid)

3D Structure for NP0000980 (Chenodeoxycholic acid)