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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:04 UTC

HMDB ID

HMDB0000637

Secondary Accession Numbers

HMDB0004013
HMDB00637
HMDB04013

Metabolite Identification

Common Name

Chenodeoxycholic acid glycine conjugate

Description

Chenodeoxycholic acid glycine conjugate is an acyl glycine and a bile acid-glycine conugate. It 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 ). This compound usually exists as the sodium salt and acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic.

Structure

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

  Mrv1652303062020112D          

 37 40  0  0  0  0            999 V2000
 9999.280110001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1424 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2822 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0025 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1424 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8549 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5675 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2801 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4298 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7153 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7153 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.4298 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1411 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1411 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8556 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5701 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.568110000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.853610000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8536 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5681 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.282610000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.2826 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0672 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5521 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.067210000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.067210001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.781910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.497510001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.211210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.926910001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.640510001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.356210001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.069810001.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.356210000.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.211210002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.352510001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.781910000.8708    0.0000 H   0  0  0  0  0  0  0  0  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11  4  1  6  0  0  0
 16  3  1  6  0  0  0
 12 14  1  0  0  0  0
 14  5  1  1  0  0  0
  9 13  1  0  0  0  0
 13  2  1  1  0  0  0
 19 13  1  0  0  0  0
 19  6  1  6  0  0  0
 16 20  1  0  0  0  0
 20  7  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 37  1  6  0  0  0
 26 27  1  0  0  0  0
 26 36  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 35  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 20 22  1  0  0  0  0
 22  8  1  6  0  0  0
 17 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END

HMDB0000637
     RDKit          3D
Chenodeoxycholic acid glycine conjugate
 75 78  0  0  0  0  0  0  0  0999 V2000
    2.5582   -0.6745   -2.9762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5771    0.4594   -2.0100 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0093    0.6899   -1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746   -0.5049   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9499   -0.2186   -0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4467    0.9041   -0.6075 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7268   -1.1816    0.3060 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0818   -0.9169    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5948   -2.1235    1.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8787   -3.1413    1.5255 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8746   -2.1175    1.9444 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094    0.3457   -0.8261 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8858    1.6034    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4896    2.0424    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    0.8088    0.2548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7521    0.9046    0.1750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2404   -0.5186    0.3656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6889   -1.3804   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600   -1.2035   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392    0.2014   -1.0679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3098    1.0387   -2.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7422   -0.6171    0.3960 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2982   -1.4925   -0.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1456   -1.2172    1.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6142   -1.3138    1.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3733   -0.0723    1.5435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4397    0.8377    2.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8551    0.6219    0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743    0.7413    0.2555 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8229    1.6764    1.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3489    1.8585    1.1799 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6868    1.8442    2.3996 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -0.6217   -3.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5979   -1.6736   -2.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7340   -0.6949   -3.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144    1.3898   -2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0830    1.5479   -0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6806    0.9337   -2.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6634   -1.3935   -1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0092   -0.7914    0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2691   -2.1226    0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7402   -0.6212   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0897   -0.0606    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3143   -1.2786    2.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150   -0.4980   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2819    2.4469   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4738    1.4365    0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    2.3367    1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    2.9253   -0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0245    0.0713    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031    1.2264   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822   -0.8576    1.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.2906   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192   -2.4544   -0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649   -1.7736   -1.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432   -1.7420   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    0.5960   -2.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5534    2.0942   -1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3519    1.1598   -3.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3691   -1.7018   -0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160   -2.4645   -0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3188   -0.8998   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6729   -0.7262    2.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395   -2.2714    1.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7878   -1.4734    3.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0322   -2.2371    1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4272   -0.3773    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8827    1.6490    2.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2708    1.6723    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2516    0.1902   -0.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1395    1.1295   -0.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0722    1.2567    2.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3976    2.6322    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    2.8923    0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397    1.0034    2.5882 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  6
 17 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 20 12  1  0
 29 22  1  0
 20 15  1  0
 31 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  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  1
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  1
 16 51  1  6
 17 52  1  1
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  6
 27 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  6
 30 72  1  0
 30 73  1  0
 31 74  1  6
 32 75  1  0
M  END

  Mrv1652303062020112D          

 37 40  0  0  0  0            999 V2000
 9999.280110001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1424 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2822 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0025 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1424 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8549 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5675 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2801 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4298 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7153 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7153 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.4298 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1411 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1411 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8556 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5701 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.568110000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.853610000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8536 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5681 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.282610000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.2826 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0672 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5521 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.067210000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.067210001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.781910001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.497510001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.211210001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.926910001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.640510001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.356210001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.069810001.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.356210000.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.211210002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.352510001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.781910000.8708    0.0000 H   0  0  0  0  0  0  0  0  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
 11  4  1  6  0  0  0
 16  3  1  6  0  0  0
 12 14  1  0  0  0  0
 14  5  1  1  0  0  0
  9 13  1  0  0  0  0
 13  2  1  1  0  0  0
 19 13  1  0  0  0  0
 19  6  1  6  0  0  0
 16 20  1  0  0  0  0
 20  7  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 37  1  6  0  0  0
 26 27  1  0  0  0  0
 26 36  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 35  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 20 22  1  0  0  0  0
 22  8  1  6  0  0  0
 17 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000637

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
GHCZAUBVMUEKKP-GYPHWSFCSA-N

> <FORMULA>
C26H43NO5

> <MOLECULAR_WEIGHT>
449.6233

> <EXACT_MASS>
449.314123491

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.11800072626717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(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]pentanamido]acetic acid

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.608022284

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.791653018199504

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7732907141500656

> <JCHEM_PKA_STRONGEST_BASIC>
-0.48930218820632587

> <JCHEM_POLAR_SURFACE_AREA>
106.85999999999999

> <JCHEM_REFRACTIVITY>
122.07729999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-03 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]pentanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000637
     RDKit          3D
Chenodeoxycholic acid glycine conjugate
 75 78  0  0  0  0  0  0  0  0999 V2000
    2.5582   -0.6745   -2.9762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5771    0.4594   -2.0100 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0093    0.6899   -1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746   -0.5049   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9499   -0.2186   -0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4467    0.9041   -0.6075 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7268   -1.1816    0.3060 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0818   -0.9169    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5948   -2.1235    1.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8787   -3.1413    1.5255 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8746   -2.1175    1.9444 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094    0.3457   -0.8261 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8858    1.6034    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4896    2.0424    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    0.8088    0.2548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7521    0.9046    0.1750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2404   -0.5186    0.3656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6889   -1.3804   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600   -1.2035   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392    0.2014   -1.0679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3098    1.0387   -2.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7422   -0.6171    0.3960 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2982   -1.4925   -0.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1456   -1.2172    1.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6142   -1.3138    1.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3733   -0.0723    1.5435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4397    0.8377    2.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8551    0.6219    0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743    0.7413    0.2555 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8229    1.6764    1.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3489    1.8585    1.1799 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6868    1.8442    2.3996 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -0.6217   -3.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5979   -1.6736   -2.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7340   -0.6949   -3.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144    1.3898   -2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0830    1.5479   -0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6806    0.9337   -2.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6634   -1.3935   -1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0092   -0.7914    0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2691   -2.1226    0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7402   -0.6212   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0897   -0.0606    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3143   -1.2786    2.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150   -0.4980   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2819    2.4469   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4738    1.4365    0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    2.3367    1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    2.9253   -0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0245    0.0713    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031    1.2264   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822   -0.8576    1.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.2906   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192   -2.4544   -0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649   -1.7736   -1.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432   -1.7420   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    0.5960   -2.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5534    2.0942   -1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3519    1.1598   -3.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3691   -1.7018   -0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160   -2.4645   -0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3188   -0.8998   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6729   -0.7262    2.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395   -2.2714    1.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7878   -1.4734    3.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0322   -2.2371    1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4272   -0.3773    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8827    1.6490    2.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2708    1.6723    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2516    0.1902   -0.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1395    1.1295   -0.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0722    1.2567    2.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3976    2.6322    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    2.8923    0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397    1.0034    2.5882 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  6
 17 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 20 12  1  0
 29 22  1  0
 20 15  1  0
 31 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  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  1
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  1
 16 51  1  6
 17 52  1  1
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  6
 27 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  6
 30 72  1  0
 30 73  1  0
 31 74  1  6
 32 75  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.3238668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8661.3328666.266   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8665.3278662.405   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8657.3388662.405   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8661.3328661.633   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8662.6628663.961   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8663.9938666.266   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8665.3238663.961   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8660.0028665.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8658.6698664.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8658.6698663.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8660.0028662.409   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.3308664.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.3308663.179   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.6648662.409   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.9988663.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.9948667.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.6608667.046   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8662.6608665.506   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8663.9948664.736   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.3288667.046   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8665.3288665.506   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8666.7928665.030   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8667.6978666.276   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8666.7928667.522   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8666.7928669.062   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8668.1268669.832   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8669.4628669.062   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8670.7948669.832   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0    8672.1308669.062   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0    8673.4628669.832   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8674.7988669.062   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0    8676.1308669.832   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0    8674.7988667.522   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0    8670.7948671.372   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0    8665.4588669.832   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0    8668.1268668.292   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   13                                                            
CONECT    3   16                                                            
CONECT    4   11                                                            
CONECT    5   14                                                            
CONECT    6   19                                                            
CONECT    7   20                                                            
CONECT    8   22                                                            
CONECT    9   10   13                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    4                                                  
CONECT   12   11   14                                                       
CONECT   13   14    9    2   19                                             
CONECT   14   13   15   12    5                                             
CONECT   15   14   16                                                       
CONECT   16   15    3   20                                                  
CONECT   17   18   21                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   13    6                                             
CONECT   20   19   16    7   22                                             
CONECT   21   22   25   17    1                                             
CONECT   22   21   23   20    8                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   26   37   21   24                                             
CONECT   26   25   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   29                                                            
CONECT   36   26                                                            
CONECT   37   25                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    HMDB0000637
HETATM    1  C1  UNL     1       2.558  -0.674  -2.976  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.577   0.459  -2.010  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.009   0.690  -1.514  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.575  -0.505  -0.828  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.950  -0.219  -0.379  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.447   0.904  -0.608  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.727  -1.182   0.306  1.00  0.00           N  
HETATM    8  C6  UNL     1       8.082  -0.917   0.755  1.00  0.00           C  
HETATM    9  C7  UNL     1       8.595  -2.124   1.426  1.00  0.00           C  
HETATM   10  O2  UNL     1       7.879  -3.141   1.526  1.00  0.00           O  
HETATM   11  O3  UNL     1       9.875  -2.118   1.944  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.709   0.346  -0.826  1.00  0.00           C  
HETATM   13  C9  UNL     1       1.886   1.603   0.006  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.490   2.042   0.430  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.270   0.809   0.255  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.752   0.905   0.175  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.240  -0.519   0.366  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.689  -1.380  -0.705  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.260  -1.204  -1.036  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.239   0.201  -1.068  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.310   1.039  -2.164  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.742  -0.617   0.396  1.00  0.00           C  
HETATM   23  C19 UNL     1      -4.298  -1.493  -0.702  1.00  0.00           C  
HETATM   24  C20 UNL     1      -4.146  -1.217   1.710  1.00  0.00           C  
HETATM   25  C21 UNL     1      -5.614  -1.314   1.920  1.00  0.00           C  
HETATM   26  C22 UNL     1      -6.373  -0.072   1.543  1.00  0.00           C  
HETATM   27  O4  UNL     1      -6.440   0.838   2.612  1.00  0.00           O  
HETATM   28  C23 UNL     1      -5.855   0.622   0.341  1.00  0.00           C  
HETATM   29  C24 UNL     1      -4.374   0.741   0.255  1.00  0.00           C  
HETATM   30  C25 UNL     1      -3.823   1.676   1.303  1.00  0.00           C  
HETATM   31  C26 UNL     1      -2.349   1.858   1.180  1.00  0.00           C  
HETATM   32  O5  UNL     1      -1.687   1.844   2.400  1.00  0.00           O  
HETATM   33  H1  UNL     1       3.502  -0.622  -3.593  1.00  0.00           H  
HETATM   34  H2  UNL     1       2.598  -1.674  -2.493  1.00  0.00           H  
HETATM   35  H3  UNL     1       1.734  -0.695  -3.679  1.00  0.00           H  
HETATM   36  H4  UNL     1       2.314   1.390  -2.558  1.00  0.00           H  
HETATM   37  H5  UNL     1       4.083   1.548  -0.819  1.00  0.00           H  
HETATM   38  H6  UNL     1       4.681   0.934  -2.369  1.00  0.00           H  
HETATM   39  H7  UNL     1       4.663  -1.393  -1.523  1.00  0.00           H  
HETATM   40  H8  UNL     1       4.009  -0.791   0.092  1.00  0.00           H  
HETATM   41  H9  UNL     1       6.269  -2.123   0.481  1.00  0.00           H  
HETATM   42  H10 UNL     1       8.740  -0.621  -0.090  1.00  0.00           H  
HETATM   43  H11 UNL     1       8.090  -0.061   1.463  1.00  0.00           H  
HETATM   44  H12 UNL     1      10.314  -1.279   2.287  1.00  0.00           H  
HETATM   45  H13 UNL     1       2.015  -0.498  -0.173  1.00  0.00           H  
HETATM   46  H14 UNL     1       2.282   2.447  -0.591  1.00  0.00           H  
HETATM   47  H15 UNL     1       2.474   1.437   0.907  1.00  0.00           H  
HETATM   48  H16 UNL     1       0.499   2.337   1.515  1.00  0.00           H  
HETATM   49  H17 UNL     1       0.134   2.925  -0.115  1.00  0.00           H  
HETATM   50  H18 UNL     1       0.024   0.071   1.033  1.00  0.00           H  
HETATM   51  H19 UNL     1      -2.103   1.226  -0.823  1.00  0.00           H  
HETATM   52  H20 UNL     1      -1.782  -0.858   1.341  1.00  0.00           H  
HETATM   53  H21 UNL     1      -2.317  -1.291  -1.614  1.00  0.00           H  
HETATM   54  H22 UNL     1      -1.819  -2.454  -0.374  1.00  0.00           H  
HETATM   55  H23 UNL     1      -0.065  -1.774  -1.969  1.00  0.00           H  
HETATM   56  H24 UNL     1       0.343  -1.742  -0.246  1.00  0.00           H  
HETATM   57  H25 UNL     1      -1.257   0.596  -2.569  1.00  0.00           H  
HETATM   58  H26 UNL     1      -0.553   2.094  -1.848  1.00  0.00           H  
HETATM   59  H27 UNL     1       0.352   1.160  -3.046  1.00  0.00           H  
HETATM   60  H28 UNL     1      -5.369  -1.702  -0.409  1.00  0.00           H  
HETATM   61  H29 UNL     1      -3.816  -2.465  -0.788  1.00  0.00           H  
HETATM   62  H30 UNL     1      -4.319  -0.900  -1.642  1.00  0.00           H  
HETATM   63  H31 UNL     1      -3.673  -0.726   2.586  1.00  0.00           H  
HETATM   64  H32 UNL     1      -3.739  -2.271   1.716  1.00  0.00           H  
HETATM   65  H33 UNL     1      -5.788  -1.473   3.025  1.00  0.00           H  
HETATM   66  H34 UNL     1      -6.032  -2.237   1.445  1.00  0.00           H  
HETATM   67  H35 UNL     1      -7.427  -0.377   1.348  1.00  0.00           H  
HETATM   68  H36 UNL     1      -6.883   1.649   2.250  1.00  0.00           H  
HETATM   69  H37 UNL     1      -6.271   1.672   0.353  1.00  0.00           H  
HETATM   70  H38 UNL     1      -6.252   0.190  -0.625  1.00  0.00           H  
HETATM   71  H39 UNL     1      -4.139   1.130  -0.779  1.00  0.00           H  
HETATM   72  H40 UNL     1      -4.072   1.257   2.293  1.00  0.00           H  
HETATM   73  H41 UNL     1      -4.398   2.632   1.225  1.00  0.00           H  
HETATM   74  H42 UNL     1      -2.181   2.892   0.756  1.00  0.00           H  
HETATM   75  H43 UNL     1      -1.240   1.003   2.588  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   20   45
CONECT   13   14   46   47
CONECT   14   15   48   49
CONECT   15   16   20   50
CONECT   16   17   31   51
CONECT   17   18   22   52
CONECT   18   19   53   54
CONECT   19   20   55   56
CONECT   20   21
CONECT   21   57   58   59
CONECT   22   23   24   29
CONECT   23   60   61   62
CONECT   24   25   63   64
CONECT   25   26   65   66
CONECT   26   27   28   67
CONECT   27   68
CONECT   28   29   69   70
CONECT   29   30   71
CONECT   30   31   72   73
CONECT   31   32   74
CONECT   32   75
END

HMDB0000637
     RDKit          3D
Chenodeoxycholic acid glycine conjugate
 75 78  0  0  0  0  0  0  0  0999 V2000
    2.5582   -0.6745   -2.9762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5771    0.4594   -2.0100 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0093    0.6899   -1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746   -0.5049   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9499   -0.2186   -0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4467    0.9041   -0.6075 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7268   -1.1816    0.3060 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0818   -0.9169    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5948   -2.1235    1.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8787   -3.1413    1.5255 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8746   -2.1175    1.9444 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094    0.3457   -0.8261 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8858    1.6034    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4896    2.0424    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    0.8088    0.2548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7521    0.9046    0.1750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2404   -0.5186    0.3656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6889   -1.3804   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600   -1.2035   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392    0.2014   -1.0679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3098    1.0387   -2.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7422   -0.6171    0.3960 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2982   -1.4925   -0.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1456   -1.2172    1.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6142   -1.3138    1.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3733   -0.0723    1.5435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4397    0.8377    2.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8551    0.6219    0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743    0.7413    0.2555 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8229    1.6764    1.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3489    1.8585    1.1799 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6868    1.8442    2.3996 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -0.6217   -3.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5979   -1.6736   -2.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7340   -0.6949   -3.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144    1.3898   -2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0830    1.5479   -0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6806    0.9337   -2.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6634   -1.3935   -1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0092   -0.7914    0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2691   -2.1226    0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7402   -0.6212   -0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0897   -0.0606    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3143   -1.2786    2.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0150   -0.4980   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2819    2.4469   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4738    1.4365    0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    2.3367    1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    2.9253   -0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0245    0.0713    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031    1.2264   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822   -0.8576    1.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.2906   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192   -2.4544   -0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649   -1.7736   -1.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432   -1.7420   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    0.5960   -2.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5534    2.0942   -1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3519    1.1598   -3.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3691   -1.7018   -0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160   -2.4645   -0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3188   -0.8998   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6729   -0.7262    2.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395   -2.2714    1.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7878   -1.4734    3.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0322   -2.2371    1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4272   -0.3773    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8827    1.6490    2.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2708    1.6723    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2516    0.1902   -0.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1395    1.1295   -0.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0722    1.2567    2.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3976    2.6322    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    2.8923    0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397    1.0034    2.5882 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  6
 17 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 20 12  1  0
 29 22  1  0
 20 15  1  0
 31 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  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  1
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  1
 16 51  1  6
 17 52  1  1
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  6
 27 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  6
 30 72  1  0
 30 73  1  0
 31 74  1  6
 32 75  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Chenodeoxycholylglycine	ChEBI
Chenodeoxyglycocholate	ChEBI
Chenodeoxyglycocholic acid	ChEBI
GCDCA	ChEBI
Glycine chenodeoxycholate	ChEBI
Glycochenodeoxycholate	ChEBI
Glycochenodeoxycholic acid	Kegg
Glycine chenodeoxycholic acid	Generator
Chenodeoxycholate glycine conjugate	Generator
Chenodeoxycholic acid glycine conjugic acid	Generator
Acid, glycochenodeoxycholic	HMDB
Chenodeoxycholate, glycine	HMDB

Chemical Formula

C₂₆H₄₃NO₅

Average Molecular Weight

449.6233

Monoisotopic Molecular Weight

449.314123491

IUPAC Name

2-[(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]pentanamido]acetic 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]pentanamido]acetic acid

CAS Registry Number

640-79-9

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)NCC(O)=O

InChI Identifier

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

InChI Key

GHCZAUBVMUEKKP-GYPHWSFCSA-N

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
Hydroxysteroid
7-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
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid glycine conjugate (CHEBI:36274 )
C26 bile acids, alcohols, and derivatives (C05466 )
Glycine conjugates (LMST05030008 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Biliary disorder

Biliary atresia (HMDB: HMDB0000637)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 27163928)
Bile (PMID: 659989)

Organ

Prostate (HMDB: HMDB0000637)
Placenta (HMDB: HMDB0000637)

Excreta

Biofluid or Excreta

Urine (PMID: 3944741)
Feces (PMID: 22664055)

Cellular substructure

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000637)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000637)

Source

Exogenous

Exogenous (HMDB: HMDB0000637)

Food

Food (HMDB: HMDB0000637)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000637)

Animal

Animal (HMDB: HMDB0000637)

Microbe

Microbe (HMDB: HMDB0000637)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000637)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0000637)
27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Zellweger Syndrome (PathBank: SMP0120715)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0120688)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000637)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0000637)

Cellular process

Cell signaling (HMDB: HMDB0000637)

Biochemical process

Lipid transport (HMDB: HMDB0000637)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000637)

Molecular messenger

Signaling molecule (HMDB: HMDB0000637)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000637)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0032 mg/mL	Not Available
LogP	2.12	RODA,A ET AL. (1990)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0079 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.61	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-0.49	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	122.08 m³·mol⁻¹	ChemAxon
Polarizability	52.12 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	250.516	30932474
DeepCCS	[M+Na]+	224.531	30932474
AllCCS	[M+H]+	211.8	32859911
AllCCS	[M+H-H2O]+	210.1	32859911
AllCCS	[M+NH4]+	213.3	32859911
AllCCS	[M+Na]+	213.8	32859911
AllCCS	[M-H]-	205.1	32859911
AllCCS	[M+Na-2H]-	207.1	32859911
AllCCS	[M+HCOO]-	209.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chenodeoxycholic acid glycine conjugate	[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)NCC(O)=O	4052.7	Standard polar	33892256
Chenodeoxycholic acid glycine conjugate	[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)NCC(O)=O	3655.0	Standard non polar	33892256
Chenodeoxycholic acid glycine conjugate	[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)NCC(O)=O	4162.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chenodeoxycholic acid glycine conjugate,1TMS,isomer #1	C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3828.5	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,1TMS,isomer #2	C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3919.4	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,1TMS,isomer #3	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3893.9	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,1TMS,isomer #4	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3918.1	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TMS,isomer #1	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3795.4	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TMS,isomer #2	C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3790.7	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TMS,isomer #3	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3762.0	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TMS,isomer #4	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3870.1	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TMS,isomer #5	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3877.7	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TMS,isomer #6	C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3864.1	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,3TMS,isomer #1	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3761.4	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,3TMS,isomer #2	C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3710.9	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,3TMS,isomer #3	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3727.2	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,3TMS,isomer #4	C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3806.6	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,4TMS,isomer #1	C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3717.1	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,4TMS,isomer #1	C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3799.2	Standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,4TMS,isomer #1	C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	4109.9	Standard polar	33892256
Chenodeoxycholic acid glycine conjugate,1TBDMS,isomer #1	C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4040.4	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,1TBDMS,isomer #2	C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4132.1	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,1TBDMS,isomer #3	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4148.0	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,1TBDMS,isomer #4	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4148.1	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TBDMS,isomer #1	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4228.5	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TBDMS,isomer #2	C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4211.3	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TBDMS,isomer #3	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4208.8	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TBDMS,isomer #4	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4312.0	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TBDMS,isomer #5	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4326.7	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,2TBDMS,isomer #6	C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4321.3	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,3TBDMS,isomer #1	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4390.9	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,3TBDMS,isomer #2	C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4368.1	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,3TBDMS,isomer #3	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4385.6	Semi standard non polar	33892256
Chenodeoxycholic acid glycine conjugate,3TBDMS,isomer #4	C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4485.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxycholic acid glycine conjugate GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate LC-ESI-IT , positive-QTOF	splash10-001i-0000900000-62ef4b27952677911202	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 10V, Positive-QTOF	splash10-0ik9-5346900000-f1bc2bb1724d840d7e4d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 40V, Positive-QTOF	splash10-005j-6930000000-d400f6a984534b53da0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 20V, Positive-QTOF	splash10-03di-1333900000-f986fe58ffb0cfb63357	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 30V, Positive-QTOF	splash10-004r-3953000000-bebc3e96086020680676	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 10V, Negative-QTOF	splash10-0002-0000900000-c5a3665989e4e01da4f5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 40V, Positive-QTOF	splash10-0rk9-5942000000-447f6ee5a3c03613d3eb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 20V, Positive-QTOF	splash10-03di-9655300000-845d2e4a556e1904a160	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 40V, Negative-QTOF	splash10-00di-9000200000-7a7111ce635d16c4297c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 10V, Positive-QTOF	splash10-03di-0000900000-d0b6aa3d2571f0956b9a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 20V, Positive-QTOF	splash10-03di-0222900000-d5866a9faa8aa048b87f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 10V, Positive-QTOF	splash10-0f89-0000900000-ebb051a2c7ea9fbbb691	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 20V, Positive-QTOF	splash10-03di-0000900000-7a109e120efc8539f76e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 0V, Positive-QTOF	splash10-03e9-0000900000-18f55fc84e29ad005446	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 40V, Positive-QTOF	splash10-004r-9654000000-be25f1da9328e657569c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 0V, Positive-QTOF	splash10-03e9-0000900000-c65d292494d94a287caf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 10V, Positive-QTOF	splash10-03di-0000900000-93a3a9a0c79a0f4a448a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 30V, Positive-QTOF	splash10-01si-6930500000-70e2e81d4fc775dac1d7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 10V, Positive-QTOF	splash10-03di-0000900000-81811f199ffa0e22682d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 10V, Positive-QTOF	splash10-00e9-7001900000-5c674a4196bbe5921395	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 20V, Positive-QTOF	splash10-00di-9002100000-4253862988128e5343db	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 40V, Positive-QTOF	splash10-00di-9001000000-8c0e27e07cce4587ddaa	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 10V, Negative-QTOF	splash10-0002-0001900000-1e432b0f0b5728b038db	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 20V, Negative-QTOF	splash10-008a-3104900000-5e705b527c1bedaf73b8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxycholic acid glycine conjugate 40V, Negative-QTOF	splash10-00dl-9101000000-bfc254147e11f3a6e4d2	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Urine

Tissue Locations

Placenta
Prostate

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bile	Detected and Quantified	>0.01 uM	Adult (>18 years old)	Both	Normal	659989	details
Blood	Detected and Quantified	0.06 +/- 0.01 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ... Basel, Switzerlan... West Cadwell, N.J...	details
Blood	Detected and Quantified	1.3(1.1-1.4) uM	Infant (0-1 year old)	Both	Normal	27163928	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected and Quantified	22.28 +/- 15.65 nmol/g dry feces	Not Specified	Not Specified	Normal	22664055	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0013 +/- 0.0026 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	3944741	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	6.5(3.3-13.3) uM	Infant (0-1 year old)	Both	Severe acute malnutrition	27163928	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Recurrent Clostridium difficile infection	24284963	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Recurrent Clostridium difficile infection	24284963	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	24284963	details
Urine	Detected and Quantified	0.032 +/- 0.058 umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	3944741	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Biliary atresia
Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. [PubMed:3944741 ]

Associated OMIM IDs

114500 (Colorectal cancer)
210500 (Biliary atresia)

External Links

DrugBank ID

DB02123

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05466

BioCyc ID

GLYCOCHENODEOXYCHOLIC_ACID

BiGG ID

Not Available

Wikipedia Link

Glycochenodeoxycholic_acid

METLIN ID

Not Available

PubChem Compound

12544

PDB ID

Not Available

ChEBI ID

36274

Food Biomarker Ontology

Not Available

VMH ID

DGCHOL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Parmentier G; Eyssen H Synthesis and characteristics of the specific monosulfates of chenodeoxycholate, deoxycholate and their taurine or glycine conjugates. Steroids (1977), 30(5), 583-90.

Material Safety Data Sheet (MSDS)

Not Available

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 G: Radioimmunoassay of bile acids in serum. Clin Chem. 1976 May;22(5):602-6. [PubMed:1261008 ]
Makino I, Shinozaki K, Nakagawa S, Mashimo K: Measurement of sulfated and nonsulfated bile acids in human serum and urine. J Lipid Res. 1974 Mar;15(2):132-8. [PubMed:4832755 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Bile acid-CoA:amino acid N-acyltransferase

General function:: Involved in thiolester hydrolase activity
Specific function:: Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:: BAAT
Uniprot ID:: Q14032
Molecular weight:: 46298.865

Reactions

Chenodeoxycholoyl-CoA + Glycine → Chenodeoxycholic acid glycine conjugate + Coenzyme A	details

Enzyme Details

2. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Enzyme Details

3. Glycine N-acyltransferase-like protein 1

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:: GLYATL1
Uniprot ID:: Q969I3
Molecular weight:: 35100.895

Enzyme Details

4. Glycine N-acyltransferase-like protein 2

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:: GLYATL2
Uniprot ID:: Q8WU03
Molecular weight:: 34277.055

Enzyme Details

5. Glycine N-acyltransferase-like protein 3

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:: GLYATL3
Uniprot ID:: Q5SZD4
Molecular weight:: 32703.3

Showing metabocard for Chenodeoxycholic acid glycine conjugate (HMDB0000637)

MOL for HMDB0000637 (Chenodeoxycholic acid glycine conjugate)

3D MOL for HMDB0000637 (Chenodeoxycholic acid glycine conjugate)

3D SDF for HMDB0000637 (Chenodeoxycholic acid glycine conjugate)

3D-SDF for HMDB0000637 (Chenodeoxycholic acid glycine conjugate)

PDB for HMDB0000637 (Chenodeoxycholic acid glycine conjugate)

3D PDB for HMDB0000637 (Chenodeoxycholic acid glycine conjugate)

SMILES for HMDB0000637 (Chenodeoxycholic acid glycine conjugate)

INCHI for HMDB0000637 (Chenodeoxycholic acid glycine conjugate)

Structure for HMDB0000637 (Chenodeoxycholic acid glycine conjugate)

3D Structure for HMDB0000637 (Chenodeoxycholic acid glycine conjugate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions