NP-MRD: Showing NP-Card for Deoxycholic acid glycine conjugate (NP0001016)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:41:49 UTC

NP-MRD ID

NP0001016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Deoxycholic acid glycine conjugate

Description

Deoxycholic acid glycine conjugate, or or Deoxyglycocholic acid or Deoxygcholylglycine is a bile salt formed in the liver by conjugation of deoxycholate with glycine. It usually exists as the sodium salt. Deoxygcholylglycine is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID: 16949895 ). As a bile acid Deoxyglycocholic acid acts as a detergent to solubilize fats for absorption and is itself absorbed. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH, and consequently require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.G. Membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). Deoxyglycocholic acid is used as a cholagogue and choleretic.

Structure

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

Deoxycholic acid glycine conjugate.mol
  Mrv1652305271900082D          

 33 36  0  0  0  0            999 V2000
    3.0902    3.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798    2.3620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    2.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5069    3.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    3.5859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727   -3.1308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1727   -2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -3.1308    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0292   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148   -3.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148   -2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -1.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -0.8133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4393   -0.0287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8559    0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694    1.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8663    1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2462    0.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997   -1.0683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4859   -0.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148   -0.6558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0292   -1.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -2.3058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7437   -1.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497    0.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148    0.1692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871   -3.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -3.9558    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  1  0  0  0
 17 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  1  0  0  0
 21 30  2  0  0  0  0
 25 31  1  6  0  0  0
  6 32  1  6  0  0  0
 10 33  1  1  0  0  0
  2 21  1  0  0  0  0
M  END

HMDB0000631
     RDKit          3D
Deoxycholic acid glycine conjugate
 75 78  0  0  0  0  0  0  0  0999 V2000
    3.2105    1.8700    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9212    0.8940    1.3293 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0680    0.1063    1.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8307   -0.7960    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234   -0.2741   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9175    0.9220   -0.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1486   -1.1656   -1.1132 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9260   -0.7004   -2.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1806   -0.0141   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4437    0.0968   -0.5919 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9965    0.4701   -2.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7420    0.0333    1.0130 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5343   -0.9849    2.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1099   -1.4378    2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4085   -0.6957    0.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589   -0.4396    0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6967   -1.6929    1.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1487   -1.3676    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4108    0.0021    0.3761 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8440    0.1731    0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2882   -0.5765   -1.1907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7040   -1.8690   -0.8113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082   -0.6096   -2.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8818   -0.8172   -1.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5530    0.2433   -0.8326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8726    1.5809   -1.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1199    0.2195   -0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699    1.5556   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    1.4705   -0.1854 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7219    1.1746   -1.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698    0.6332    0.9880 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0261    1.3323    2.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1081    2.5197    0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4176    2.6788    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488    1.5065   -0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784    1.5225    2.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209   -0.3472    2.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7975    0.9037    2.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -1.7133    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067   -1.3017    1.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9161   -2.1730   -0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2374   -1.5780   -2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3422   -0.0499   -2.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6802    1.1781   -2.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728   -0.5674    0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856   -1.8575    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7283   -0.5697    3.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -2.5369    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4618   -1.2930    3.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1107   -1.1642   -0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373    0.2643    1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5132   -2.0771    2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560   -2.4959    0.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6755   -1.4388    1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6372   -2.1261    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.7350    1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0791    1.2717   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4628   -0.2013    0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2257   -0.0812   -1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6653   -1.8588   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5660   -1.5044   -2.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3931    0.2579   -3.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -1.8342   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -0.6052   -2.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3564    1.6111   -2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    2.4319   -0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9460    1.7212   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5797   -0.4184   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902    2.0546   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234    2.1513    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2779    2.5451    0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2907    0.4935   -1.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    0.6586    3.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    2.1859    2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910    1.7656    2.1793 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
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  1
 31 12  1  0
 31 15  1  0
 27 16  1  0
 25 19  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 12 45  1  6
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 13 47  1  0
 14 48  1  0
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 15 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
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 23 62  1  0
 24 63  1  0
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 26 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  1
 30 72  1  0
 32 73  1  0
 32 74  1  0
 32 75  1  0
M  END

Deoxycholic acid glycine conjugate.mol
  Mrv1652305271900082D          

 33 36  0  0  0  0            999 V2000
    3.0902    3.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798    2.3620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    2.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5069    3.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8871    3.5859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727   -3.1308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1727   -2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -3.1308    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0292   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148   -3.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148   -2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -1.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -0.8133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4393   -0.0287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8559    0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694    1.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8663    1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2462    0.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997   -1.0683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4859   -0.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148   -0.6558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0292   -1.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -2.3058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7437   -1.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497    0.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148    0.1692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871   -3.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -3.9558    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  1  0  0  0
 17 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  1  0  0  0
 21 30  2  0  0  0  0
 25 31  1  6  0  0  0
  6 32  1  6  0  0  0
 10 33  1  1  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CCC3C4CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]4(C)[C@@H](O)CC3[C@@]1(C)CC[C@@H](O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18?,19-,20?,21?,22+,25+,26-/m1/s1

> <INCHI_KEY>
WVULKSPCQVQLCU-ZMBDPXIHSA-N

> <FORMULA>
C26H43NO5

> <MOLECULAR_WEIGHT>
449.6233

> <EXACT_MASS>
449.314123491

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.10965735325514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.6859760140000004

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.83785540472606

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7733019985645173

> <JCHEM_PKA_STRONGEST_BASIC>
-0.32033464930455235

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
122.00029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000631
     RDKit          3D
Deoxycholic acid glycine conjugate
 75 78  0  0  0  0  0  0  0  0999 V2000
    3.2105    1.8700    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9212    0.8940    1.3293 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0680    0.1063    1.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8307   -0.7960    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234   -0.2741   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9175    0.9220   -0.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1486   -1.1656   -1.1132 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9260   -0.7004   -2.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1806   -0.0141   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4437    0.0968   -0.5919 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9965    0.4701   -2.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7420    0.0333    1.0130 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5343   -0.9849    2.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1099   -1.4378    2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4085   -0.6957    0.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589   -0.4396    0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6967   -1.6929    1.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1487   -1.3676    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4108    0.0021    0.3761 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8440    0.1731    0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2882   -0.5765   -1.1907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7040   -1.8690   -0.8113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082   -0.6096   -2.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8818   -0.8172   -1.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5530    0.2433   -0.8326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8726    1.5809   -1.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1199    0.2195   -0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699    1.5556   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    1.4705   -0.1854 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7219    1.1746   -1.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698    0.6332    0.9880 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0261    1.3323    2.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1081    2.5197    0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4176    2.6788    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488    1.5065   -0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784    1.5225    2.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209   -0.3472    2.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7975    0.9037    2.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -1.7133    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067   -1.3017    1.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9161   -2.1730   -0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2374   -1.5780   -2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3422   -0.0499   -2.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6802    1.1781   -2.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728   -0.5674    0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856   -1.8575    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7283   -0.5697    3.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -2.5369    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4618   -1.2930    3.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1107   -1.1642   -0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373    0.2643    1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5132   -2.0771    2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560   -2.4959    0.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6755   -1.4388    1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6372   -2.1261    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.7350    1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0791    1.2717   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4628   -0.2013    0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2257   -0.0812   -1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6653   -1.8588   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5660   -1.5044   -2.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3931    0.2579   -3.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -1.8342   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -0.6052   -2.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3564    1.6111   -2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    2.4319   -0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9460    1.7212   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5797   -0.4184   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902    2.0546   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234    2.1513    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2779    2.5451    0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2907    0.4935   -1.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    0.6586    3.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    2.1859    2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910    1.7656    2.1793 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
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  1
 31 12  1  0
 31 15  1  0
 27 16  1  0
 25 19  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 12 45  1  6
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  1
 20 57  1  0
 20 58  1  0
 21 59  1  6
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  1
 30 72  1  0
 32 73  1  0
 32 74  1  0
 32 75  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Deoxycholic acid glycine conjugate.mol            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       5.768   6.295   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.882   4.409   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.370   4.808   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.680   7.384   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.256   6.694   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.922  -5.844   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.922  -4.304   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.589  -3.534   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.589  -6.614   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.255  -5.844   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.921  -6.614   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.588  -5.844   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.588  -4.304   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.746  -3.534   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.211  -4.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.116  -2.764   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.211  -1.518   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.687  -0.054   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.598   1.035   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.996   2.523   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.484   2.922   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.193   0.267   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.746  -1.994   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.907  -0.463   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.588  -1.224   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.921  -1.994   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.921  -3.534   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.255  -4.304   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.255  -2.764   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.573   1.833   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.588   0.316   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -7.256  -6.614   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0      -3.255  -7.384   0.000  0.00  0.00           H+0
CONECT    1    3    4    5                                                  
CONECT    2    3   21                                                       
CONECT    3    2    1                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    7    9   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7   28                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11   28   33                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   27                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   30    2                                                  
CONECT   22   18                                                            
CONECT   23   17   14   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   13   28                                                  
CONECT   28   27    8   10   29                                             
CONECT   29   28                                                            
CONECT   30   21                                                            
CONECT   31   25                                                            
CONECT   32    6                                                            
CONECT   33   10                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000631
HETATM    1  C1  UNL     1       3.210   1.870   0.258  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.921   0.894   1.329  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.068   0.106   1.866  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.831  -0.796   1.018  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.623  -0.274  -0.092  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.917   0.922  -0.272  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.149  -1.166  -1.113  1.00  0.00           N  
HETATM    8  C6  UNL     1       6.926  -0.700  -2.214  1.00  0.00           C  
HETATM    9  C7  UNL     1       8.181  -0.014  -1.798  1.00  0.00           C  
HETATM   10  O2  UNL     1       8.444   0.097  -0.592  1.00  0.00           O  
HETATM   11  O3  UNL     1       8.997   0.470  -2.813  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.742   0.033   1.013  1.00  0.00           C  
HETATM   13  C9  UNL     1       1.534  -0.985   2.151  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.110  -1.438   2.079  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.409  -0.696   0.892  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.859  -0.440   0.898  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.697  -1.693   1.032  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.149  -1.368   0.926  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.411   0.002   0.376  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.844   0.173   0.016  1.00  0.00           C  
HETATM   21  C17 UNL     1      -6.288  -0.577  -1.191  1.00  0.00           C  
HETATM   22  O4  UNL     1      -6.704  -1.869  -0.811  1.00  0.00           O  
HETATM   23  C18 UNL     1      -5.308  -0.610  -2.310  1.00  0.00           C  
HETATM   24  C19 UNL     1      -3.882  -0.817  -1.868  1.00  0.00           C  
HETATM   25  C20 UNL     1      -3.553   0.243  -0.833  1.00  0.00           C  
HETATM   26  C21 UNL     1      -3.873   1.581  -1.462  1.00  0.00           C  
HETATM   27  C22 UNL     1      -2.120   0.219  -0.467  1.00  0.00           C  
HETATM   28  C23 UNL     1      -1.470   1.556  -0.429  1.00  0.00           C  
HETATM   29  C24 UNL     1       0.022   1.470  -0.185  1.00  0.00           C  
HETATM   30  O5  UNL     1       0.722   1.175  -1.327  1.00  0.00           O  
HETATM   31  C25 UNL     1       0.370   0.633   0.988  1.00  0.00           C  
HETATM   32  C26 UNL     1       0.026   1.332   2.289  1.00  0.00           C  
HETATM   33  H1  UNL     1       4.108   2.520   0.505  1.00  0.00           H  
HETATM   34  H2  UNL     1       2.418   2.679   0.175  1.00  0.00           H  
HETATM   35  H3  UNL     1       3.349   1.506  -0.751  1.00  0.00           H  
HETATM   36  H4  UNL     1       2.578   1.522   2.223  1.00  0.00           H  
HETATM   37  H5  UNL     1       3.721  -0.347   2.828  1.00  0.00           H  
HETATM   38  H6  UNL     1       4.797   0.904   2.246  1.00  0.00           H  
HETATM   39  H7  UNL     1       4.240  -1.713   0.694  1.00  0.00           H  
HETATM   40  H8  UNL     1       5.607  -1.302   1.704  1.00  0.00           H  
HETATM   41  H9  UNL     1       5.916  -2.173  -0.984  1.00  0.00           H  
HETATM   42  H10 UNL     1       7.237  -1.578  -2.814  1.00  0.00           H  
HETATM   43  H11 UNL     1       6.342  -0.050  -2.918  1.00  0.00           H  
HETATM   44  H12 UNL     1       9.680   1.178  -2.562  1.00  0.00           H  
HETATM   45  H13 UNL     1       1.873  -0.567   0.096  1.00  0.00           H  
HETATM   46  H14 UNL     1       2.186  -1.857   1.903  1.00  0.00           H  
HETATM   47  H15 UNL     1       1.728  -0.570   3.136  1.00  0.00           H  
HETATM   48  H16 UNL     1       0.028  -2.537   1.838  1.00  0.00           H  
HETATM   49  H17 UNL     1      -0.462  -1.293   3.001  1.00  0.00           H  
HETATM   50  H18 UNL     1      -0.111  -1.164  -0.046  1.00  0.00           H  
HETATM   51  H19 UNL     1      -2.237   0.264   1.657  1.00  0.00           H  
HETATM   52  H20 UNL     1      -2.513  -2.077   2.064  1.00  0.00           H  
HETATM   53  H21 UNL     1      -2.356  -2.496   0.350  1.00  0.00           H  
HETATM   54  H22 UNL     1      -4.676  -1.439   1.916  1.00  0.00           H  
HETATM   55  H23 UNL     1      -4.637  -2.126   0.276  1.00  0.00           H  
HETATM   56  H24 UNL     1      -4.163   0.735   1.171  1.00  0.00           H  
HETATM   57  H25 UNL     1      -6.079   1.272  -0.025  1.00  0.00           H  
HETATM   58  H26 UNL     1      -6.463  -0.201   0.884  1.00  0.00           H  
HETATM   59  H27 UNL     1      -7.226  -0.081  -1.574  1.00  0.00           H  
HETATM   60  H28 UNL     1      -7.665  -1.859  -0.539  1.00  0.00           H  
HETATM   61  H29 UNL     1      -5.566  -1.504  -2.950  1.00  0.00           H  
HETATM   62  H30 UNL     1      -5.393   0.258  -3.012  1.00  0.00           H  
HETATM   63  H31 UNL     1      -3.696  -1.834  -1.528  1.00  0.00           H  
HETATM   64  H32 UNL     1      -3.231  -0.605  -2.743  1.00  0.00           H  
HETATM   65  H33 UNL     1      -3.356   1.611  -2.447  1.00  0.00           H  
HETATM   66  H34 UNL     1      -3.561   2.432  -0.803  1.00  0.00           H  
HETATM   67  H35 UNL     1      -4.946   1.721  -1.662  1.00  0.00           H  
HETATM   68  H36 UNL     1      -1.580  -0.418  -1.206  1.00  0.00           H  
HETATM   69  H37 UNL     1      -1.590   2.055  -1.433  1.00  0.00           H  
HETATM   70  H38 UNL     1      -1.923   2.151   0.382  1.00  0.00           H  
HETATM   71  H39 UNL     1       0.278   2.545   0.094  1.00  0.00           H  
HETATM   72  H40 UNL     1       0.291   0.493  -1.873  1.00  0.00           H  
HETATM   73  H41 UNL     1       0.121   0.659   3.134  1.00  0.00           H  
HETATM   74  H42 UNL     1       0.697   2.186   2.420  1.00  0.00           H  
HETATM   75  H43 UNL     1      -0.991   1.766   2.179  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   12   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6    6    7
CONECT    7    8   41
CONECT    8    9   42   43
CONECT    9   10   10   11
CONECT   11   44
CONECT   12   13   31   45
CONECT   13   14   46   47
CONECT   14   15   48   49
CONECT   15   16   31   50
CONECT   16   17   27   51
CONECT   17   18   52   53
CONECT   18   19   54   55
CONECT   19   20   25   56
CONECT   20   21   57   58
CONECT   21   22   23   59
CONECT   22   60
CONECT   23   24   61   62
CONECT   24   25   63   64
CONECT   25   26   27
CONECT   26   65   66   67
CONECT   27   28   68
CONECT   28   29   69   70
CONECT   29   30   31   71
CONECT   30   72
CONECT   31   32
CONECT   32   73   74   75
END

HMDB0000631
     RDKit          3D
Deoxycholic acid glycine conjugate
 75 78  0  0  0  0  0  0  0  0999 V2000
    3.2105    1.8700    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9212    0.8940    1.3293 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0680    0.1063    1.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8307   -0.7960    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234   -0.2741   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9175    0.9220   -0.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1486   -1.1656   -1.1132 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9260   -0.7004   -2.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1806   -0.0141   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4437    0.0968   -0.5919 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9965    0.4701   -2.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7420    0.0333    1.0130 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5343   -0.9849    2.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1099   -1.4378    2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4085   -0.6957    0.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589   -0.4396    0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6967   -1.6929    1.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1487   -1.3676    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4108    0.0021    0.3761 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8440    0.1731    0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2882   -0.5765   -1.1907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7040   -1.8690   -0.8113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082   -0.6096   -2.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8818   -0.8172   -1.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5530    0.2433   -0.8326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8726    1.5809   -1.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1199    0.2195   -0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699    1.5556   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    1.4705   -0.1854 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7219    1.1746   -1.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698    0.6332    0.9880 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0261    1.3323    2.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1081    2.5197    0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4176    2.6788    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3488    1.5065   -0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784    1.5225    2.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209   -0.3472    2.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7975    0.9037    2.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -1.7133    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067   -1.3017    1.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9161   -2.1730   -0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2374   -1.5780   -2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3422   -0.0499   -2.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6802    1.1781   -2.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728   -0.5674    0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856   -1.8575    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7283   -0.5697    3.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -2.5369    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4618   -1.2930    3.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1107   -1.1642   -0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373    0.2643    1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5132   -2.0771    2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560   -2.4959    0.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6755   -1.4388    1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6372   -2.1261    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.7350    1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0791    1.2717   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4628   -0.2013    0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2257   -0.0812   -1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6653   -1.8588   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5660   -1.5044   -2.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3931    0.2579   -3.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6961   -1.8342   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -0.6052   -2.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3564    1.6111   -2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    2.4319   -0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9460    1.7212   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5797   -0.4184   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902    2.0546   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234    2.1513    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2779    2.5451    0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2907    0.4935   -1.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    0.6586    3.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    2.1859    2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910    1.7656    2.1793 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
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  1
 31 12  1  0
 31 15  1  0
 27 16  1  0
 25 19  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 12 45  1  6
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  1
 20 57  1  0
 20 58  1  0
 21 59  1  6
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  1
 30 72  1  0
 32 73  1  0
 32 74  1  0
 32 75  1  0
M  END

View in JSmol

Synonyms

Value	Source
Deoxycholate glycine conjugate	Generator
Deoxycholic acid glycine conjugic acid	Generator
Deoxycholylglycine	HMDB
Deoxyglycocholate	HMDB
Deoxyglycocholic acid	HMDB
Glycodeoxycholate	HMDB
Glycodeoxycholic acid	HMDB
Glycodesoxycholate	HMDB
Glycodesoxycholic acid	HMDB
Glycyldeoxycholate	HMDB
Glycyldeoxycholic acid	HMDB
N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-glycine	HMDB
N-(Carboxymethyl)-3a,12a-dihydroxy-5b-cholan-24-amide	HMDB
Deoxycholate, glycine	HMDB
Acid, glycodeoxycholic	HMDB
Glycine deoxycholate	HMDB

Chemical Formula

C₂₆H₄₃NO₅

Average Mass

449.6233 Da

Monoisotopic Mass

449.31412 Da

IUPAC Name

2-[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

360-65-6

SMILES

[H][C@]12CCC3C4CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]4(C)[C@@H](O)CC3[C@@]1(C)CC[C@@H](O)C2

InChI Identifier

InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18?,19-,20?,21?,22+,25+,26-/m1/s1

InChI Key

WVULKSPCQVQLCU-ZMBDPXIHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, 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
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Streptomyces nigra	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Penicillium sp. SA29	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents

Substituents

Glycinated bile acid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Fatty amide
Fatty acyl
N-acyl-amine
Cyclic alcohol
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0027 mg/mL	Not Available
LogP	2.25	Roda, A., Minutello, A., Angellotti, M. A., & Fini, A. (1990). Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. Journal of lipid research, 31(8), 1433-1443.

Predicted Properties

Property	Value	Source
Water Solubility	0.0078 g/L	ALOGPS
logP	2.69	ALOGPS
logP	2.69	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-0.32	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122 m³·mol⁻¹	ChemAxon
Polarizability	52.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000631

DrugBank ID

Not Available

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

Not Available

METLIN ID

5604

PubChem Compound

22833539

PDB ID

Not Available

ChEBI ID

27471

Good Scents ID

Not Available

References

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Hepner GW, Demers LM: Dynamics of the enterohepatic circulation of the glycine conjugates of cholic, chenodeoxycholic, deoxycholic, and sulfolithocholic acid in man. Gastroenterology. 1977 Mar;72(3):499-501. [PubMed:832799 ]
Bloch CA, Watkins JB: Determination of conjugated bile acids in human bile and duodenal fluid by reverse-phase high-performance liquid chromatography. J Lipid Res. 1978 May;19(4):510-3. [PubMed:659989 ]
Demers LM, Hepner GW: Levels of immunoreactive glycine-conjugated bile acids in health and hepatobiliary disease. Am J Clin Pathol. 1976 Nov;66(5):831-9. [PubMed:983991 ]
Demers LM, Hepner G: Radioimmunoassay of bile acids in serum. Clin Chem. 1976 May;22(5):602-6. [PubMed:1261008 ]
Goto T, Myint KT, Sato K, Wada O, Kakiyama G, Iida T, Hishinuma T, Mano N, Goto J: LC/ESI-tandem mass spectrometric determination of bile acid 3-sulfates in human urine 3beta-Sulfooxy-12alpha-hydroxy-5beta-cholanoic acid is an abundant nonamidated sulfate. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):69-77. Epub 2006 Sep 1. [PubMed:16949895 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]

Showing NP-Card for Deoxycholic acid glycine conjugate (NP0001016)

MOL for NP0001016 (Deoxycholic acid glycine conjugate)

3D MOL for NP0001016 (Deoxycholic acid glycine conjugate)

3D SDF for NP0001016 (Deoxycholic acid glycine conjugate)

3D-SDF for NP0001016 (Deoxycholic acid glycine conjugate)

PDB for NP0001016 (Deoxycholic acid glycine conjugate)

3D PDB for NP0001016 (Deoxycholic acid glycine conjugate)

SMILES for NP0001016 (Deoxycholic acid glycine conjugate)

INCHI for NP0001016 (Deoxycholic acid glycine conjugate)

Structure for NP0001016 (Deoxycholic acid glycine conjugate)

3D Structure for NP0001016 (Deoxycholic acid glycine conjugate)