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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:59 UTC

Update Date

2022-03-07 02:49:16 UTC

HMDB ID

HMDB0002639

Secondary Accession Numbers

HMDB02639

Metabolite Identification

Common Name

Sulfolithocholylglycine

Description

Sulfolithocholylglycine is an acyl glycine and a bile acid-glycine conjugate. 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 ). Sulfolithocholylglycine is a sulfated bile acid which has a greater renal clearance rate than lithocholylglycine.

Structure

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

  Mrv1652303062020152D          

 40 43  0  0  0  0            999 V2000
10000.021310001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7435 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0289 9998.1285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6153 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4405 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3103 9997.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5962 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3087 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0213 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8823 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8823 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5968 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3113 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.309310000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594810000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5948 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3093 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.023810000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0238 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.8084 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2933 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.808410000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.808410001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.524110001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.237710001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.667010001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.382710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.812010001.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310000.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.093710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.524110000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  2  0  0  0  0
  4  7  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22  3  1  6  0  0  0
 23 13  1  0  0  0  0
 13  8  1  1  0  0  0
 20 12  1  0  0  0  0
 12  2  1  1  0  0  0
 18 12  1  0  0  0  0
 18  9  1  6  0  0  0
 15 19  1  0  0  0  0
 19 10  1  1  0  0  0
 28 29  1  0  0  0  0
 28 40  1  6  0  0  0
 29 30  1  0  0  0  0
 29 39  1  6  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 38  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 19 25  1  0  0  0  0
 25 11  1  6  0  0  0
 16 24  1  0  0  0  0
 24  1  1  1  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
M  END

HMDB0002639
     RDKit          3D
Sulfolithocholylglycine
 78 81  0  0  0  0  0  0  0  0999 V2000
    3.4766   -2.1192   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272   -0.7060   -0.7679 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4377    0.1034   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -0.4238   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8217    0.4379   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5922    1.4093    0.4978 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1893    0.2002   -0.6052 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2596    0.9998   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3531    0.9931    1.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5814    0.3601    2.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3707    1.7460    1.9510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0230   -0.0699   -0.1760 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8992    1.3194   -0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319    1.2523   -1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904    0.4685   -0.4773 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6061    0.1555   -0.7006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3743    1.4612   -0.7669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084    1.1290   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922   -0.2628   -0.6323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6814   -0.3445   -0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2716    0.2184    0.7058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3633    1.6024    0.7024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9493    2.1423    0.7640 S   0  0  0  0  0  6  0  0  0  0  0  0
   -8.7686    1.2367   -0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4928    2.0623    2.1602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1054    3.6995    0.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6115   -0.2764    1.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1356   -0.0196    1.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5233   -0.7154    0.6453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8527   -2.1982    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0649   -0.5164    0.6034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2592   -1.7860    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151   -1.4582    0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187   -0.7619   -0.3533 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6104   -1.6699   -1.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8059   -2.1256    0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -2.7606   -0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323   -2.5855   -0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2862   -0.6855   -1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3300    1.1854   -0.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5057    0.0102    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   -0.4877   -1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9529   -1.4425   -0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3855   -0.6012   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1689    2.0635   -0.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2180    0.6031   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7889    2.5548    1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    0.0030    0.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6904    1.5554   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124    2.0388    0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462    2.2484   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409    0.6558   -2.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.9872    0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8737   -0.4234   -1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2642    1.9855    0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9226    2.1036   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9606    1.1928   -2.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363    1.9175   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8615   -0.9766   -1.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0758   -1.3670   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0898    0.2705   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3359   -0.1590    0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2384    4.1206    0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9848    0.3348    2.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8746   -1.3184    2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9977    1.0870    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6439   -0.3941    2.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -2.5779    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9581   -2.3696    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3960   -2.7847   -0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7239    0.1653    1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5655   -2.2770    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3797   -2.4809   -0.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7185   -2.4087    1.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3911   -0.7737    1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429   -2.6872   -1.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2096   -1.3921   -2.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251   -1.6730   -2.1704 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
 22 23  1  0
 23 24  2  0
 23 25  2  0
 23 26  1  0
 21 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  6
 34 12  1  0
 34 15  1  0
 31 16  1  0
 29 19  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  6
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
 11 47  1  0
 12 48  1  1
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  1
 16 54  1  6
 17 55  1  0
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 18 57  1  0
 18 58  1  0
 19 59  1  6
 20 60  1  0
 20 61  1  0
 21 62  1  1
 26 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 30 68  1  0
 30 69  1  0
 30 70  1  0
 31 71  1  1
 32 72  1  0
 32 73  1  0
 33 74  1  0
 33 75  1  0
 35 76  1  0
 35 77  1  0
 35 78  1  0
M  END

  Mrv1652303062020152D          

 40 43  0  0  0  0            999 V2000
10000.021310001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7435 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0289 9998.1285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6153 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4405 9998.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3103 9997.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5962 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3087 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0213 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8823 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8823 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5968 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3113 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.309310000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594810000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5948 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3093 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.023810000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0238 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.8084 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2933 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.808410000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.808410001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.524110001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.237710001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.667010001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.382710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.812010001.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310000.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.093710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.524110000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  2  0  0  0  0
  4  7  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22  3  1  6  0  0  0
 23 13  1  0  0  0  0
 13  8  1  1  0  0  0
 20 12  1  0  0  0  0
 12  2  1  1  0  0  0
 18 12  1  0  0  0  0
 18  9  1  6  0  0  0
 15 19  1  0  0  0  0
 19 10  1  1  0  0  0
 28 29  1  0  0  0  0
 28 40  1  6  0  0  0
 29 30  1  0  0  0  0
 29 39  1  6  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 38  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 19 25  1  0  0  0  0
 25 11  1  6  0  0  0
 16 24  1  0  0  0  0
 24  1  1  1  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002639

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

> <INCHI_KEY>
FHXBAFXQVZOILS-OETIFKLTSA-N

> <FORMULA>
C26H43NO7S

> <MOLECULAR_WEIGHT>
513.69

> <EXACT_MASS>
513.276023903

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.914850737132326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
2.6445759787310394

> <ALOGPS_LOGS>
-6.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.773272809670727

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.0995010181869347

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7149687684002468

> <JCHEM_POLAR_SURFACE_AREA>
130.0

> <JCHEM_REFRACTIVITY>
130.47659999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.82e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002639
     RDKit          3D
Sulfolithocholylglycine
 78 81  0  0  0  0  0  0  0  0999 V2000
    3.4766   -2.1192   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272   -0.7060   -0.7679 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4377    0.1034   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -0.4238   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8217    0.4379   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5922    1.4093    0.4978 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1893    0.2002   -0.6052 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2596    0.9998   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3531    0.9931    1.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5814    0.3601    2.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3707    1.7460    1.9510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0230   -0.0699   -0.1760 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8992    1.3194   -0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319    1.2523   -1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904    0.4685   -0.4773 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6061    0.1555   -0.7006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3743    1.4612   -0.7669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084    1.1290   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922   -0.2628   -0.6323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6814   -0.3445   -0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2716    0.2184    0.7058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3633    1.6024    0.7024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9493    2.1423    0.7640 S   0  0  0  0  0  6  0  0  0  0  0  0
   -8.7686    1.2367   -0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4928    2.0623    2.1602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1054    3.6995    0.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6115   -0.2764    1.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1356   -0.0196    1.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5233   -0.7154    0.6453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8527   -2.1982    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0649   -0.5164    0.6034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2592   -1.7860    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151   -1.4582    0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187   -0.7619   -0.3533 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6104   -1.6699   -1.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8059   -2.1256    0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -2.7606   -0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323   -2.5855   -0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2862   -0.6855   -1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3300    1.1854   -0.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5057    0.0102    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   -0.4877   -1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9529   -1.4425   -0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3855   -0.6012   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1689    2.0635   -0.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2180    0.6031   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7889    2.5548    1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    0.0030    0.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6904    1.5554   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124    2.0388    0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462    2.2484   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409    0.6558   -2.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.9872    0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8737   -0.4234   -1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2642    1.9855    0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9226    2.1036   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9606    1.1928   -2.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363    1.9175   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8615   -0.9766   -1.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0758   -1.3670   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0898    0.2705   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3359   -0.1590    0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2384    4.1206    0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9848    0.3348    2.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8746   -1.3184    2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9977    1.0870    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6439   -0.3941    2.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -2.5779    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9581   -2.3696    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3960   -2.7847   -0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7239    0.1653    1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5655   -2.2770    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3797   -2.4809   -0.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7185   -2.4087    1.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3911   -0.7737    1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429   -2.6872   -1.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2096   -1.3921   -2.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251   -1.6730   -2.1704 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
 22 23  1  0
 23 24  2  0
 23 25  2  0
 23 26  1  0
 21 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  6
 34 12  1  0
 34 15  1  0
 31 16  1  0
 29 19  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  6
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
 11 47  1  0
 12 48  1  1
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  1
 16 54  1  6
 17 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  6
 20 60  1  0
 20 61  1  0
 21 62  1  1
 26 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 30 68  1  0
 30 69  1  0
 30 70  1  0
 31 71  1  1
 32 72  1  0
 32 73  1  0
 33 74  1  0
 33 75  1  0
 35 76  1  0
 35 77  1  0
 35 78  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    8666.7068668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.7168666.266   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.7218662.405   0.000  0.00  0.00           O+0
HETATM    4  S   UNK     0    8657.3878663.173   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0    8656.6158664.507   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8658.1568664.507   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8656.0468662.401   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8662.7168661.633   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8664.0468663.961   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0    8665.3768666.266   0.000  0.00  0.00           H+0
HETATM   11  H   UNK     0    8666.7068663.961   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0    8662.7148664.719   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.7148663.179   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0478662.409   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.3818663.179   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.3778667.816   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.0448667.046   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.0448665.506   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.3778664.736   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.3868665.489   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8660.0528664.719   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8660.0528663.179   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8661.3868662.409   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8666.7118667.046   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8666.7118665.506   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.1768665.030   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8669.0818666.276   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8668.1768667.522   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8668.1768669.062   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8669.5128669.832   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8670.8448669.062   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8672.1808669.832   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0    8673.5128669.062   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0    8674.8488669.832   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8676.1808669.062   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0    8677.5168669.832   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0    8676.1808667.522   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0    8672.1808671.372   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0    8666.8428669.832   0.000  0.00  0.00           C+0
HETATM   40  H   UNK     0    8669.5128668.292   0.000  0.00  0.00           H+0
CONECT    1   24                                                            
CONECT    2   12                                                            
CONECT    3    4   22                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8   13                                                            
CONECT    9   18                                                            
CONECT   10   19                                                            
CONECT   11   25                                                            
CONECT   12   13   20    2   18                                             
CONECT   13   12   14   23    8                                             
CONECT   14   13   15                                                       
CONECT   15   14   19                                                       
CONECT   16   17   24                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   12    9                                             
CONECT   19   18   15   10   25                                             
CONECT   20   21   12                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23    3                                                  
CONECT   23   22   13                                                       
CONECT   24   25   16    1   28                                             
CONECT   25   24   26   19   11                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   29   40   24   27                                             
CONECT   29   28   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   32                                                            
CONECT   39   29                                                            
CONECT   40   28                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

COMPND    HMDB0002639
HETATM    1  C1  UNL     1       3.477  -2.119  -0.265  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.227  -0.706  -0.768  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.438   0.103  -0.274  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.726  -0.424  -0.812  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.822   0.438  -0.272  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.592   1.409   0.498  1.00  0.00           O  
HETATM    7  N1  UNL     1       8.189   0.200  -0.605  1.00  0.00           N  
HETATM    8  C6  UNL     1       9.260   1.000  -0.110  1.00  0.00           C  
HETATM    9  C7  UNL     1       9.353   0.993   1.374  1.00  0.00           C  
HETATM   10  O2  UNL     1       8.581   0.360   2.113  1.00  0.00           O  
HETATM   11  O3  UNL     1      10.371   1.746   1.951  1.00  0.00           O  
HETATM   12  C8  UNL     1       2.023  -0.070  -0.176  1.00  0.00           C  
HETATM   13  C9  UNL     1       1.899   1.319  -0.783  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.532   1.252  -1.489  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.190   0.468  -0.477  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.606   0.155  -0.701  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.374   1.461  -0.767  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.808   1.129  -1.037  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.192  -0.263  -0.632  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.681  -0.345  -0.545  1.00  0.00           C  
HETATM   21  C17 UNL     1      -6.272   0.218   0.706  1.00  0.00           C  
HETATM   22  O4  UNL     1      -6.363   1.602   0.702  1.00  0.00           O  
HETATM   23  S1  UNL     1      -7.949   2.142   0.764  1.00  0.00           S  
HETATM   24  O5  UNL     1      -8.769   1.237  -0.120  1.00  0.00           O  
HETATM   25  O6  UNL     1      -8.493   2.062   2.160  1.00  0.00           O  
HETATM   26  O7  UNL     1      -8.105   3.699   0.212  1.00  0.00           O  
HETATM   27  C18 UNL     1      -5.611  -0.276   1.961  1.00  0.00           C  
HETATM   28  C19 UNL     1      -4.136  -0.020   1.857  1.00  0.00           C  
HETATM   29  C20 UNL     1      -3.523  -0.715   0.645  1.00  0.00           C  
HETATM   30  C21 UNL     1      -3.853  -2.198   0.813  1.00  0.00           C  
HETATM   31  C22 UNL     1      -2.065  -0.516   0.603  1.00  0.00           C  
HETATM   32  C23 UNL     1      -1.259  -1.786   0.743  1.00  0.00           C  
HETATM   33  C24 UNL     1       0.215  -1.458   0.888  1.00  0.00           C  
HETATM   34  C25 UNL     1       0.719  -0.762  -0.353  1.00  0.00           C  
HETATM   35  C26 UNL     1       0.610  -1.670  -1.518  1.00  0.00           C  
HETATM   36  H1  UNL     1       3.806  -2.126   0.795  1.00  0.00           H  
HETATM   37  H2  UNL     1       2.577  -2.761  -0.319  1.00  0.00           H  
HETATM   38  H3  UNL     1       4.332  -2.585  -0.838  1.00  0.00           H  
HETATM   39  H4  UNL     1       3.286  -0.686  -1.868  1.00  0.00           H  
HETATM   40  H5  UNL     1       4.330   1.185  -0.453  1.00  0.00           H  
HETATM   41  H6  UNL     1       4.506   0.010   0.852  1.00  0.00           H  
HETATM   42  H7  UNL     1       5.760  -0.488  -1.913  1.00  0.00           H  
HETATM   43  H8  UNL     1       5.953  -1.443  -0.428  1.00  0.00           H  
HETATM   44  H9  UNL     1       8.386  -0.601  -1.242  1.00  0.00           H  
HETATM   45  H10 UNL     1       9.169   2.063  -0.436  1.00  0.00           H  
HETATM   46  H11 UNL     1      10.218   0.603  -0.498  1.00  0.00           H  
HETATM   47  H12 UNL     1      10.789   2.555   1.473  1.00  0.00           H  
HETATM   48  H13 UNL     1       2.209   0.003   0.929  1.00  0.00           H  
HETATM   49  H14 UNL     1       2.690   1.555  -1.517  1.00  0.00           H  
HETATM   50  H15 UNL     1       1.812   2.039   0.041  1.00  0.00           H  
HETATM   51  H16 UNL     1       0.146   2.248  -1.704  1.00  0.00           H  
HETATM   52  H17 UNL     1       0.741   0.656  -2.422  1.00  0.00           H  
HETATM   53  H18 UNL     1      -0.096   0.987   0.512  1.00  0.00           H  
HETATM   54  H19 UNL     1      -1.874  -0.423  -1.574  1.00  0.00           H  
HETATM   55  H20 UNL     1      -2.264   1.986   0.194  1.00  0.00           H  
HETATM   56  H21 UNL     1      -1.923   2.104  -1.551  1.00  0.00           H  
HETATM   57  H22 UNL     1      -3.961   1.193  -2.149  1.00  0.00           H  
HETATM   58  H23 UNL     1      -4.436   1.918  -0.596  1.00  0.00           H  
HETATM   59  H24 UNL     1      -3.861  -0.977  -1.430  1.00  0.00           H  
HETATM   60  H25 UNL     1      -6.076  -1.367  -0.686  1.00  0.00           H  
HETATM   61  H26 UNL     1      -6.090   0.271  -1.399  1.00  0.00           H  
HETATM   62  H27 UNL     1      -7.336  -0.159   0.751  1.00  0.00           H  
HETATM   63  H28 UNL     1      -7.238   4.121   0.024  1.00  0.00           H  
HETATM   64  H29 UNL     1      -5.985   0.335   2.812  1.00  0.00           H  
HETATM   65  H30 UNL     1      -5.875  -1.318   2.187  1.00  0.00           H  
HETATM   66  H31 UNL     1      -3.998   1.087   1.793  1.00  0.00           H  
HETATM   67  H32 UNL     1      -3.644  -0.394   2.760  1.00  0.00           H  
HETATM   68  H33 UNL     1      -3.582  -2.578   1.803  1.00  0.00           H  
HETATM   69  H34 UNL     1      -4.958  -2.370   0.697  1.00  0.00           H  
HETATM   70  H35 UNL     1      -3.396  -2.785  -0.028  1.00  0.00           H  
HETATM   71  H36 UNL     1      -1.724   0.165   1.411  1.00  0.00           H  
HETATM   72  H37 UNL     1      -1.565  -2.277   1.703  1.00  0.00           H  
HETATM   73  H38 UNL     1      -1.380  -2.481  -0.093  1.00  0.00           H  
HETATM   74  H39 UNL     1       0.719  -2.409   1.117  1.00  0.00           H  
HETATM   75  H40 UNL     1       0.391  -0.774   1.748  1.00  0.00           H  
HETATM   76  H41 UNL     1       0.343  -2.687  -1.167  1.00  0.00           H  
HETATM   77  H42 UNL     1      -0.210  -1.392  -2.228  1.00  0.00           H  
HETATM   78  H43 UNL     1       1.525  -1.673  -2.170  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3   12   39
CONECT    3    4   40   41
CONECT    4    5   42   43
CONECT    5    6    6    7
CONECT    7    8   44
CONECT    8    9   45   46
CONECT    9   10   10   11
CONECT   11   47
CONECT   12   13   34   48
CONECT   13   14   49   50
CONECT   14   15   51   52
CONECT   15   16   34   53
CONECT   16   17   31   54
CONECT   17   18   55   56
CONECT   18   19   57   58
CONECT   19   20   29   59
CONECT   20   21   60   61
CONECT   21   22   27   62
CONECT   22   23
CONECT   23   24   24   25   25
CONECT   23   26
CONECT   26   63
CONECT   27   28   64   65
CONECT   28   29   66   67
CONECT   29   30   31
CONECT   30   68   69   70
CONECT   31   32   71
CONECT   32   33   72   73
CONECT   33   34   74   75
CONECT   34   35
CONECT   35   76   77   78
END

HMDB0002639
     RDKit          3D
Sulfolithocholylglycine
 78 81  0  0  0  0  0  0  0  0999 V2000
    3.4766   -2.1192   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272   -0.7060   -0.7679 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4377    0.1034   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -0.4238   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8217    0.4379   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5922    1.4093    0.4978 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1893    0.2002   -0.6052 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2596    0.9998   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3531    0.9931    1.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5814    0.3601    2.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3707    1.7460    1.9510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0230   -0.0699   -0.1760 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8992    1.3194   -0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319    1.2523   -1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904    0.4685   -0.4773 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6061    0.1555   -0.7006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3743    1.4612   -0.7669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084    1.1290   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922   -0.2628   -0.6323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6814   -0.3445   -0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2716    0.2184    0.7058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3633    1.6024    0.7024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9493    2.1423    0.7640 S   0  0  0  0  0  6  0  0  0  0  0  0
   -8.7686    1.2367   -0.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4928    2.0623    2.1602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1054    3.6995    0.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6115   -0.2764    1.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1356   -0.0196    1.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5233   -0.7154    0.6453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8527   -2.1982    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0649   -0.5164    0.6034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2592   -1.7860    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151   -1.4582    0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187   -0.7619   -0.3533 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6104   -1.6699   -1.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8059   -2.1256    0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -2.7606   -0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323   -2.5855   -0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2862   -0.6855   -1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3300    1.1854   -0.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5057    0.0102    0.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   -0.4877   -1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9529   -1.4425   -0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3855   -0.6012   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1689    2.0635   -0.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2180    0.6031   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7889    2.5548    1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    0.0030    0.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6904    1.5554   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124    2.0388    0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1462    2.2484   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409    0.6558   -2.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.9872    0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8737   -0.4234   -1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2642    1.9855    0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9226    2.1036   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9606    1.1928   -2.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363    1.9175   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8615   -0.9766   -1.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0758   -1.3670   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0898    0.2705   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3359   -0.1590    0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2384    4.1206    0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9848    0.3348    2.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8746   -1.3184    2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9977    1.0870    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6439   -0.3941    2.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -2.5779    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9581   -2.3696    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3960   -2.7847   -0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7239    0.1653    1.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5655   -2.2770    1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3797   -2.4809   -0.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7185   -2.4087    1.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3911   -0.7737    1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429   -2.6872   -1.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2096   -1.3921   -2.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251   -1.6730   -2.1704 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
 22 23  1  0
 23 24  2  0
 23 25  2  0
 23 26  1  0
 21 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  6
 34 12  1  0
 34 15  1  0
 31 16  1  0
 29 19  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  6
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
 11 47  1  0
 12 48  1  1
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  1
 16 54  1  6
 17 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  6
 20 60  1  0
 20 61  1  0
 21 62  1  1
 26 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 30 68  1  0
 30 69  1  0
 30 70  1  0
 31 71  1  1
 32 72  1  0
 32 73  1  0
 33 74  1  0
 33 75  1  0
 35 76  1  0
 35 77  1  0
 35 78  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Glycolithocholate 3-sulfate	ChEBI
Glycolithocholate sulfate	ChEBI
Glycolithocholic acid 3-sulfate	ChEBI
Glycolithocholic acid sulfate	ChEBI
Sulfoglycolithocholate	ChEBI
Glycolithocholate 3-sulphate	Generator
Glycolithocholic acid 3-sulfuric acid	Generator
Glycolithocholic acid 3-sulphuric acid	Generator
Glycolithocholate sulphate	Generator
Glycolithocholic acid sulfuric acid	Generator
Glycolithocholic acid sulphuric acid	Generator
Sulfoglycolithocholic acid	Generator
Sulphoglycolithocholate	Generator
Sulphoglycolithocholic acid	Generator
Sulpholithocholylglycine	Generator
Sulfolithoglycocholine	HMDB
3alpha-Hydroxy-5beta-cholanoylglycine 3-sulfate	HMDB
3alpha-Hydroxy-5beta-cholanoylglycine 3-sulphate	HMDB
3Α-hydroxy-5β-cholanoylglycine 3-sulfate	HMDB
3Α-hydroxy-5β-cholanoylglycine 3-sulphate	HMDB
Glycolithocholic acid 3-sulphate	HMDB
Glycolithocholic acid 3alpha-sulfate	HMDB
Glycolithocholic acid 3alpha-sulphate	HMDB
Glycolithocholic acid 3α-sulfate	HMDB
Glycolithocholic acid 3α-sulphate	HMDB
Glycolithocholic acid sulphate	HMDB
N-[(3alpha,5beta)-24-oxo-3-(Sulfooxy)cholan-24-yl]glycine	HMDB
N-[(3Α,5β)-24-oxo-3-(sulfooxy)cholan-24-yl]glycine	HMDB
Sulfolithocholylglycine	ChEBI

Chemical Formula

C₂₆H₄₃NO₇S

Average Molecular Weight

513.69

Monoisotopic Molecular Weight

513.276023903

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

15324-64-8

SMILES

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

InChI Identifier

InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

InChI Key

FHXBAFXQVZOILS-OETIFKLTSA-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
Sulfated steroid skeleton
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Sulfuric acid monoester
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Organic sulfuric acid or derivatives
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:9347 )
bile acid glycine conjugate (CHEBI:9347 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Cirrhosis (HMDB: HMDB0002639)
Hepatitis (HMDB: HMDB0002639)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 12231118)
Feces (PMID: 22664055)

Cellular substructure

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0002639)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002639)

Source

Endogenous

Endogenous (HMDB: HMDB0002639)

Animal

Animal (HMDB: HMDB0002639)

Microbe

Microbe (HMDB: HMDB0002639)

Exogenous

Food

Food (HMDB: HMDB0002639)

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)

Exogenous (HMDB: HMDB0002639)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002639)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002639)

Lipid metabolism pathway (HMDB: HMDB0002639)

Cellular process

Cell signaling (HMDB: HMDB0002639)

Biochemical process

Lipid transport (HMDB: HMDB0002639)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002639)

Molecular messenger

Signaling molecule (HMDB: HMDB0002639)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002639)

Pharmaceutical industry

Biomarker

Cirrhosis (MarkerDB: MDB00000393)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00038 g/L	ALOGPS
logP	1.1	ALOGPS
logP	2.64	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	-1.1	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.48 m³·mol⁻¹	ChemAxon
Polarizability	56.91 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]-	259.61	30932474
DeepCCS	[M+Na]+	233.615	30932474
AllCCS	[M+H]+	220.6	32859911
AllCCS	[M+H-H2O]+	219.2	32859911
AllCCS	[M+NH4]+	221.8	32859911
AllCCS	[M+Na]+	222.2	32859911
AllCCS	[M-H]-	212.2	32859911
AllCCS	[M+Na-2H]-	214.8	32859911
AllCCS	[M+HCOO]-	217.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulfolithocholylglycine	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O	4754.6	Standard polar	33892256
Sulfolithocholylglycine	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O	3817.6	Standard non polar	33892256
Sulfolithocholylglycine	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O	4424.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulfolithocholylglycine,1TMS,isomer #1	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C	4202.0	Semi standard non polar	33892256
Sulfolithocholylglycine,1TMS,isomer #2	C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4258.7	Semi standard non polar	33892256
Sulfolithocholylglycine,1TMS,isomer #3	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C	4194.1	Semi standard non polar	33892256
Sulfolithocholylglycine,2TMS,isomer #1	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4192.1	Semi standard non polar	33892256
Sulfolithocholylglycine,2TMS,isomer #1	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4302.4	Standard non polar	33892256
Sulfolithocholylglycine,2TMS,isomer #1	C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	5211.0	Standard polar	33892256
Sulfolithocholylglycine,2TMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C	4168.3	Semi standard non polar	33892256
Sulfolithocholylglycine,2TMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C	4350.7	Standard non polar	33892256
Sulfolithocholylglycine,2TMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C	5320.7	Standard polar	33892256
Sulfolithocholylglycine,2TMS,isomer #3	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4183.5	Semi standard non polar	33892256
Sulfolithocholylglycine,2TMS,isomer #3	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4324.2	Standard non polar	33892256
Sulfolithocholylglycine,2TMS,isomer #3	C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	5212.5	Standard polar	33892256
Sulfolithocholylglycine,3TMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4133.3	Semi standard non polar	33892256
Sulfolithocholylglycine,3TMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4499.9	Standard non polar	33892256
Sulfolithocholylglycine,3TMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	5091.9	Standard polar	33892256
Sulfolithocholylglycine,1TBDMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C	4473.2	Semi standard non polar	33892256
Sulfolithocholylglycine,1TBDMS,isomer #2	C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4435.6	Semi standard non polar	33892256
Sulfolithocholylglycine,1TBDMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C	4464.6	Semi standard non polar	33892256
Sulfolithocholylglycine,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4619.9	Semi standard non polar	33892256
Sulfolithocholylglycine,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4878.9	Standard non polar	33892256
Sulfolithocholylglycine,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	5278.7	Standard polar	33892256
Sulfolithocholylglycine,2TBDMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C	4694.8	Semi standard non polar	33892256
Sulfolithocholylglycine,2TBDMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C	4920.1	Standard non polar	33892256
Sulfolithocholylglycine,2TBDMS,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C	5393.9	Standard polar	33892256
Sulfolithocholylglycine,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4635.0	Semi standard non polar	33892256
Sulfolithocholylglycine,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4887.5	Standard non polar	33892256
Sulfolithocholylglycine,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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	5301.0	Standard polar	33892256
Sulfolithocholylglycine,3TBDMS,isomer #1	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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4801.5	Semi standard non polar	33892256
Sulfolithocholylglycine,3TBDMS,isomer #1	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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	5332.3	Standard non polar	33892256
Sulfolithocholylglycine,3TBDMS,isomer #1	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]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	5183.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfolithocholylglycine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2022-08-08	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfolithocholylglycine 10V, Positive-QTOF	splash10-03di-0002790000-c099ed28a9d3fe4a476b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfolithocholylglycine 20V, Positive-QTOF	splash10-02g5-1049100000-52a84ab9604d814a9bd5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfolithocholylglycine 40V, Positive-QTOF	splash10-0btd-9477100000-6f4f03809ede3852eade	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfolithocholylglycine 10V, Negative-QTOF	splash10-03di-0000290000-879dd3634ce8aaed563b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfolithocholylglycine 20V, Negative-QTOF	splash10-03dj-6001960000-a87cd597b61e8c4ca6fb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfolithocholylglycine 40V, Negative-QTOF	splash10-0229-9000020000-4ef0fbad6b90715b1275	2021-09-24	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

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.06 +/- 0.01 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	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	1.26 +/- 1.24 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	0.0691 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	12231118	details
Urine	Detected and Quantified	0.112 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	12231118	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	0.684 umol/mmol creatinine	Adult (>18 years old)	Both	Hepatitis	12231118	details
Urine	Detected and Quantified	1.150 (0.044-5.349) umol/mmol creatinine	Adult (>18 years old)	Both	Hepatitis	12231118	details
Urine	Detected and Quantified	1.771 umol/mmol creatinine	Adult (>18 years old)	Both	Cirrhosis	12231118	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 ]
Hepatitis
Kobayashi N, Katsumata H, Uto Y, Goto J, Niwa T, Kobayashi K, Mizuuchi Y: A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test. Steroids. 2002 Sep;67(10):827-33. [PubMed:12231118 ]
Cirrhosis
Kobayashi N, Katsumata H, Uto Y, Goto J, Niwa T, Kobayashi K, Mizuuchi Y: A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test. Steroids. 2002 Sep;67(10):827-33. [PubMed:12231118 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023034

KNApSAcK ID

Not Available

Chemspider ID

65188

KEGG Compound ID

C11301

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72222

PDB ID

Not Available

ChEBI ID

9347

Food Biomarker Ontology

Not Available

VMH ID

HC02197

MarkerDB ID

MDB00000393

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
Cowen AE, Korman MG, Hofmann AF, Cass OW, Coffin SB: Metabolism of lithocholate in healthy man. II. Enterohepatic circulation. Gastroenterology. 1975 Jul;69(1):67-76. [PubMed:1097294 ]
Cowen AE, Korman MG, Hofmann AF, Cass OW: Metabolism of lethocholate in healthy man. I. Biotransformation and biliary excretion of intravenously administered lithocholate, lithocholylglycine, and their sulfates. Gastroenterology. 1975 Jul;69(1):59-66. [PubMed:1150035 ]
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 ]
Kobayashi N, Katsumata H, Uto Y, Goto J, Niwa T, Kobayashi K, Mizuuchi Y: A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test. Steroids. 2002 Sep;67(10):827-33. [PubMed:12231118 ]
Kirkpatrick RB, Belsaas RA: Formation and secretion of glycolithocholate-3-sulfate in primary hepatocyte cultures. J Lipid Res. 1985 Dec;26(12):1431-7. [PubMed:4086945 ]

Enzymes

Enzyme Details

1. Bile salt sulfotransferase

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name:: SULT2A1
Uniprot ID:: Q06520
Molecular weight:: 33779.57

Reactions

Phosphoadenosine phosphosulfate + Lithocholic acid glycine conjugate → Adenosine 3',5'-diphosphate + Sulfolithocholylglycine	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 Sulfolithocholylglycine (HMDB0002639)

MOL for HMDB0002639 (Sulfolithocholylglycine)

3D MOL for HMDB0002639 (Sulfolithocholylglycine)

3D SDF for HMDB0002639 (Sulfolithocholylglycine)

3D-SDF for HMDB0002639 (Sulfolithocholylglycine)

PDB for HMDB0002639 (Sulfolithocholylglycine)

3D PDB for HMDB0002639 (Sulfolithocholylglycine)

SMILES for HMDB0002639 (Sulfolithocholylglycine)

INCHI for HMDB0002639 (Sulfolithocholylglycine)

Structure for HMDB0002639 (Sulfolithocholylglycine)

3D Structure for HMDB0002639 (Sulfolithocholylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions