NP-MRD: Showing NP-Card for Glycocholic acid (NP0000833)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:41:47 UTC

NP-MRD ID

NP0000833

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glycocholic acid

Description

Glycocholic acid 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 ). More specifically, glycocholic acid or cholylglycine, is a crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. Its anion is called glycocholate. As the glycine conjugate of cholic acid, this compound acts as a detergent to solubilize fats for absorption and is itself absorbed (PubChem). Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.G., Membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). Glycocholic acid is found to be associated with alpha-1-antitrypsin deficiency, which is an inborn error of metabolism.

Structure

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


  Mrv1652307301920072D          

 33 36  0  0  1  0            999 V2000
   -0.3987    0.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 23  2  0  0  0  0
 33 23  1  0  0  0  0
M  END

HMDB0000138
     RDKit          3D
Glycocholic acid
 76 79  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652307301920072D          

 33 36  0  0  1  0            999 V2000
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 22  7  1  0  0  0  0
 23 13  1  0  0  0  0
 18 24  1  0  0  0  0
 24 19  1  6  0  0  0
 24 20  1  0  0  0  0
 25  2  1  1  0  0  0
 25  9  1  0  0  0  0
 25 15  1  0  0  0  0
 19 25  1  0  0  0  0
 26  3  1  1  0  0  0
 26 17  1  0  0  0  0
 26 18  1  0  0  0  0
 21 26  1  0  0  0  0
 27 13  1  4  0  0  0
 27 22  2  0  0  0  0
 16 28  1  6  0  0  0
 20 29  1  6  0  0  0
 21 30  1  6  0  0  0
 31 22  1  0  0  0  0
 32 23  2  0  0  0  0
 33 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000833

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1

> <INCHI_KEY>
RFDAIACWWDREDC-FRVQLJSFSA-N

> <FORMULA>
C26H43NO6

> <MOLECULAR_WEIGHT>
465.6227

> <EXACT_MASS>
465.309038113

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.79738571393794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <JCHEM_LOGP>
1.3772112169999984

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.694897850593033

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7733200967259095

> <JCHEM_PKA_STRONGEST_BASIC>
-0.13936410783518716

> <JCHEM_POLAR_SURFACE_AREA>
127.09

> <JCHEM_REFRACTIVITY>
123.59279999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000138
     RDKit          3D
Glycocholic acid
 76 79  0  0  0  0  0  0  0  0999 V2000
   -2.7035    1.7836   -2.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    0.5192   -1.3727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0960    0.4269   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3306    0.4660   -1.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4815    0.3572   -0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6529    1.3169    0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3184   -0.6058   -0.5701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4542   -0.7457    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0102   -1.1992    1.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7902   -1.3900    1.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8785   -1.4136    2.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6922    0.3164   -0.3993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8974   -0.9997    0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4957   -1.6089    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3620   -0.4301    0.2731 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8009   -0.6370    0.1104 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4344    0.7606    0.0224 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8760    1.3966   -1.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.5402   -1.1209 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0506    2.3734   -0.0738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141    0.2052   -0.9561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2148   -0.6537   -2.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    0.6859    0.0648 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4796    1.3900   -1.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4117    1.4592    1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5636    0.8565    1.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5077    0.0778    1.1250 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3042   -0.7003    1.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9085   -0.8100    0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073   -0.7262    0.0034 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8082   -1.6573    0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3481   -1.3756    1.2943 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1761   -0.7314    2.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2849    2.6353   -1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    2.1064   -2.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869    1.6187   -3.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748   -0.3197   -2.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1285   -0.4856    0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1605    1.2727    0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3982   -0.3669   -2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4668    1.4596   -1.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9989    1.3107    1.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8655    0.2898    0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2506   -1.3629   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1232   -0.7237    3.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7135    1.1719    0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5455   -1.6952   -0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2705   -0.7819    1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -2.0938    1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -2.3202   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1847    0.2980    1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -1.1640   -0.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209    1.3442    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349    0.8343   -2.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946    2.4191   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383    1.9985   -2.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    3.3171   -0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6610   -1.3292   -2.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0790    0.0312   -3.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1040   -1.3081   -2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    2.4800   -1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727    0.9100   -2.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5986    1.2507   -1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5719    1.5838    1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520    2.5234    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979    0.2865    2.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1548    1.7051    2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2432    0.7643    0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5080   -0.2378    2.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3478   -0.6349   -0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1396   -1.8957    0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1493   -1.1039   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -1.7768    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237   -2.6931    0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582   -2.3369    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752    0.0978    2.4711 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  1  0
  5  7  2  3
  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
 19 21  1  0
 21 22  1  6
 17 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 21 12  1  0
 30 23  1  0
 21 15  1  0
 32 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  6
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  6 42  1  0
  8 43  1  0
  8 44  1  0
 11 45  1  0
 12 46  1  1
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  1
 16 52  1  6
 17 53  1  1
 18 54  1  0
 18 55  1  0
 19 56  1  6
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 24 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  6
 28 69  1  0
 29 70  1  0
 29 71  1  0
 30 72  1  6
 31 73  1  0
 31 74  1  0
 32 75  1  1
 33 76  1  0
M  END

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0      -0.744   0.803   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.290   1.123   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.594   0.373   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.362  -0.834   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.298   3.288   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.573   4.152   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.416  -2.050   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.322   1.665   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.806   1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.853   4.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.344   5.198   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.774   0.852   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.632  -6.118   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.781   0.593   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.337   4.020   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.845   3.114   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.726   1.809   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.789   3.207   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.298   2.301   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.828   4.926   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.258   0.581   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.997  -3.476   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.313  -7.334   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.305   3.478   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.813   2.572   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.266   1.759   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       0.052  -4.692   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0      12.361   3.385   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.835   6.104   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.735  -0.867   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.522  -3.687   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.267  -8.761   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.839  -7.123   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4    7   14                                                       
CONECT    5    6   17                                                       
CONECT    6    5   18                                                       
CONECT    7    4   22                                                       
CONECT    8    9   16                                                       
CONECT    9    8   25                                                       
CONECT   10   15   16                                                       
CONECT   11   15   20                                                       
CONECT   12   19   21                                                       
CONECT   13   23   27                                                       
CONECT   14    1    4   17                                                  
CONECT   15   10   11   25                                                  
CONECT   16    8   10   28                                                  
CONECT   17    5   14   26                                                  
CONECT   18    6   24   26                                                  
CONECT   19   12   24   25                                                  
CONECT   20   11   24   29                                                  
CONECT   21   12   26   30                                                  
CONECT   22    7   27   31                                                  
CONECT   23   13   32   33                                                  
CONECT   24   18   19   20                                                  
CONECT   25    2    9   15   19                                             
CONECT   26    3   17   18   21                                             
CONECT   27   13   22                                                       
CONECT   28   16                                                            
CONECT   29   20                                                            
CONECT   30   21                                                            
CONECT   31   22                                                            
CONECT   32   23                                                            
CONECT   33   23                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000138
HETATM    1  C1  UNL     1      -2.703   1.784  -2.155  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.801   0.519  -1.373  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.096   0.427  -0.572  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.331   0.466  -1.406  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.481   0.357  -0.483  1.00  0.00           C  
HETATM    6  O1  UNL     1      -6.653   1.317   0.490  1.00  0.00           O  
HETATM    7  N1  UNL     1      -7.318  -0.606  -0.570  1.00  0.00           N  
HETATM    8  C6  UNL     1      -8.454  -0.746   0.312  1.00  0.00           C  
HETATM    9  C7  UNL     1      -8.010  -1.199   1.669  1.00  0.00           C  
HETATM   10  O2  UNL     1      -6.790  -1.390   1.863  1.00  0.00           O  
HETATM   11  O3  UNL     1      -8.878  -1.414   2.703  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.692   0.316  -0.399  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.897  -1.000   0.322  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.496  -1.609   0.493  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.362  -0.430   0.273  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.801  -0.637   0.110  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.434   0.761   0.022  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.876   1.397  -1.214  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.383   1.540  -1.121  1.00  0.00           C  
HETATM   20  O4  UNL     1       0.051   2.373  -0.074  1.00  0.00           O  
HETATM   21  C16 UNL     1      -0.314   0.205  -0.956  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.215  -0.654  -2.170  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.913   0.686   0.065  1.00  0.00           C  
HETATM   24  C19 UNL     1       4.480   1.390  -1.179  1.00  0.00           C  
HETATM   25  C20 UNL     1       4.412   1.459   1.248  1.00  0.00           C  
HETATM   26  C21 UNL     1       5.564   0.856   1.959  1.00  0.00           C  
HETATM   27  C22 UNL     1       6.508   0.078   1.125  1.00  0.00           C  
HETATM   28  O5  UNL     1       7.304  -0.700   1.995  1.00  0.00           O  
HETATM   29  C23 UNL     1       5.908  -0.810   0.106  1.00  0.00           C  
HETATM   30  C24 UNL     1       4.407  -0.726   0.003  1.00  0.00           C  
HETATM   31  C25 UNL     1       3.808  -1.657   0.988  1.00  0.00           C  
HETATM   32  C26 UNL     1       2.348  -1.376   1.294  1.00  0.00           C  
HETATM   33  O6  UNL     1       2.176  -0.731   2.497  1.00  0.00           O  
HETATM   34  H1  UNL     1      -2.285   2.635  -1.584  1.00  0.00           H  
HETATM   35  H2  UNL     1      -3.683   2.106  -2.546  1.00  0.00           H  
HETATM   36  H3  UNL     1      -2.087   1.619  -3.088  1.00  0.00           H  
HETATM   37  H4  UNL     1      -2.875  -0.320  -2.123  1.00  0.00           H  
HETATM   38  H5  UNL     1      -4.129  -0.486   0.054  1.00  0.00           H  
HETATM   39  H6  UNL     1      -4.161   1.273   0.151  1.00  0.00           H  
HETATM   40  H7  UNL     1      -5.398  -0.367  -2.132  1.00  0.00           H  
HETATM   41  H8  UNL     1      -5.467   1.460  -1.916  1.00  0.00           H  
HETATM   42  H9  UNL     1      -5.999   1.311   1.286  1.00  0.00           H  
HETATM   43  H10 UNL     1      -8.865   0.290   0.474  1.00  0.00           H  
HETATM   44  H11 UNL     1      -9.251  -1.363  -0.105  1.00  0.00           H  
HETATM   45  H12 UNL     1      -9.123  -0.724   3.408  1.00  0.00           H  
HETATM   46  H13 UNL     1      -1.713   1.172   0.309  1.00  0.00           H  
HETATM   47  H14 UNL     1      -2.545  -1.695  -0.251  1.00  0.00           H  
HETATM   48  H15 UNL     1      -2.271  -0.782   1.342  1.00  0.00           H  
HETATM   49  H16 UNL     1      -0.395  -2.094   1.481  1.00  0.00           H  
HETATM   50  H17 UNL     1      -0.357  -2.320  -0.351  1.00  0.00           H  
HETATM   51  H18 UNL     1       0.185   0.298   1.094  1.00  0.00           H  
HETATM   52  H19 UNL     1       2.126  -1.164  -0.794  1.00  0.00           H  
HETATM   53  H20 UNL     1       2.021   1.344   0.894  1.00  0.00           H  
HETATM   54  H21 UNL     1       2.135   0.834  -2.137  1.00  0.00           H  
HETATM   55  H22 UNL     1       2.295   2.419  -1.315  1.00  0.00           H  
HETATM   56  H23 UNL     1       0.038   1.998  -2.061  1.00  0.00           H  
HETATM   57  H24 UNL     1      -0.001   3.317  -0.381  1.00  0.00           H  
HETATM   58  H25 UNL     1       0.661  -1.329  -2.197  1.00  0.00           H  
HETATM   59  H26 UNL     1      -0.079   0.031  -3.058  1.00  0.00           H  
HETATM   60  H27 UNL     1      -1.104  -1.308  -2.335  1.00  0.00           H  
HETATM   61  H28 UNL     1       4.324   2.480  -1.132  1.00  0.00           H  
HETATM   62  H29 UNL     1       4.173   0.910  -2.104  1.00  0.00           H  
HETATM   63  H30 UNL     1       5.599   1.251  -1.109  1.00  0.00           H  
HETATM   64  H31 UNL     1       3.572   1.584   1.995  1.00  0.00           H  
HETATM   65  H32 UNL     1       4.652   2.523   0.952  1.00  0.00           H  
HETATM   66  H33 UNL     1       5.198   0.287   2.864  1.00  0.00           H  
HETATM   67  H34 UNL     1       6.155   1.705   2.419  1.00  0.00           H  
HETATM   68  H35 UNL     1       7.243   0.764   0.619  1.00  0.00           H  
HETATM   69  H36 UNL     1       7.508  -0.238   2.829  1.00  0.00           H  
HETATM   70  H37 UNL     1       6.348  -0.635  -0.905  1.00  0.00           H  
HETATM   71  H38 UNL     1       6.140  -1.896   0.320  1.00  0.00           H  
HETATM   72  H39 UNL     1       4.149  -1.104  -1.031  1.00  0.00           H  
HETATM   73  H40 UNL     1       4.405  -1.777   1.931  1.00  0.00           H  
HETATM   74  H41 UNL     1       3.824  -2.693   0.534  1.00  0.00           H  
HETATM   75  H42 UNL     1       1.758  -2.337   1.363  1.00  0.00           H  
HETATM   76  H43 UNL     1       1.675   0.098   2.471  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   12   37
CONECT    3    4   38   39
CONECT    4    5   40   41
CONECT    5    6    7    7
CONECT    6   42
CONECT    7    8
CONECT    8    9   43   44
CONECT    9   10   10   11
CONECT   11   45
CONECT   12   13   21   46
CONECT   13   14   47   48
CONECT   14   15   49   50
CONECT   15   16   21   51
CONECT   16   17   32   52
CONECT   17   18   23   53
CONECT   18   19   54   55
CONECT   19   20   21   56
CONECT   20   57
CONECT   21   22
CONECT   22   58   59   60
CONECT   23   24   25   30
CONECT   24   61   62   63
CONECT   25   26   64   65
CONECT   26   27   66   67
CONECT   27   28   29   68
CONECT   28   69
CONECT   29   30   70   71
CONECT   30   31   72
CONECT   31   32   73   74
CONECT   32   33   75
CONECT   33   76
END

HMDB0000138
     RDKit          3D
Glycocholic acid
 76 79  0  0  0  0  0  0  0  0999 V2000
   -2.7035    1.7836   -2.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    0.5192   -1.3727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0960    0.4269   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3306    0.4660   -1.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4815    0.3572   -0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6529    1.3169    0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3184   -0.6058   -0.5701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4542   -0.7457    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0102   -1.1992    1.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7902   -1.3900    1.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8785   -1.4136    2.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6922    0.3164   -0.3993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8974   -0.9997    0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4957   -1.6089    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3620   -0.4301    0.2731 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8009   -0.6370    0.1104 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4344    0.7606    0.0224 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8760    1.3966   -1.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.5402   -1.1209 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0506    2.3734   -0.0738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141    0.2052   -0.9561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2148   -0.6537   -2.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    0.6859    0.0648 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4796    1.3900   -1.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4117    1.4592    1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5636    0.8565    1.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5077    0.0778    1.1250 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3042   -0.7003    1.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9085   -0.8100    0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073   -0.7262    0.0034 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8082   -1.6573    0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3481   -1.3756    1.2943 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1761   -0.7314    2.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2849    2.6353   -1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    2.1064   -2.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869    1.6187   -3.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748   -0.3197   -2.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1285   -0.4856    0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1605    1.2727    0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3982   -0.3669   -2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4668    1.4596   -1.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9989    1.3107    1.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8655    0.2898    0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2506   -1.3629   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1232   -0.7237    3.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7135    1.1719    0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5455   -1.6952   -0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2705   -0.7819    1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -2.0938    1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -2.3202   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1847    0.2980    1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -1.1640   -0.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209    1.3442    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349    0.8343   -2.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946    2.4191   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383    1.9985   -2.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    3.3171   -0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6610   -1.3292   -2.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0790    0.0312   -3.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1040   -1.3081   -2.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    2.4800   -1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727    0.9100   -2.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5986    1.2507   -1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5719    1.5838    1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520    2.5234    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979    0.2865    2.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1548    1.7051    2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2432    0.7643    0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5080   -0.2378    2.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3478   -0.6349   -0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1396   -1.8957    0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1493   -1.1039   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -1.7768    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237   -2.6931    0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582   -2.3369    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752    0.0978    2.4711 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  1  0
  5  7  2  3
  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
 19 21  1  0
 21 22  1  6
 17 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 21 12  1  0
 30 23  1  0
 21 15  1  0
 32 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  6
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  6 42  1  0
  8 43  1  0
  8 44  1  0
 11 45  1  0
 12 46  1  1
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  1
 16 52  1  6
 17 53  1  1
 18 54  1  0
 18 55  1  0
 19 56  1  6
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 24 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  6
 28 69  1  0
 29 70  1  0
 29 71  1  0
 30 72  1  6
 31 73  1  0
 31 74  1  0
 32 75  1  1
 33 76  1  0
M  END

View in JSmol

Synonyms

Value	Source
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oylglycine	ChEBI
N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine	ChEBI
N-Choloylglycine	ChEBI
3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine	Generator
3Α,7α,12α-trihydroxy-5β-cholan-24-oylglycine	Generator
N-[(3a,5b,7a,12a)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine	Generator
N-[(3Α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine	Generator
Glycocholate	Generator
Glycine cholate	HMDB
Glycocholic acid, sodium salt	HMDB
Cholylglycine	HMDB
Glycocholate sodium	HMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid-24-glycine	HMDB
3alpha,7alpha,12alpha-Trihydroxy-N-(carboxymethyl)-5beta-cholan-24-amide	HMDB
3Α,7α,12α-trihydroxy-5β-cholanic acid-24-glycine	HMDB
3Α,7α,12α-trihydroxy-N-(carboxymethyl)-5β-cholan-24-amide	HMDB
Glycoreductodehydrocholic acid	HMDB
Glycylcholate	HMDB
Glycylcholic acid	HMDB
N-(Carboxymethyl)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-amide	HMDB
N-(Carboxymethyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide	HMDB
N-Choloyl-glycine	HMDB
Glycocholic acid	HMDB

Chemical Formula

C₂₆H₄₃NO₆

Average Mass

465.6227 Da

Monoisotopic Mass

465.30904 Da

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-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,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

475-31-0

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])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1

InChI Key

RFDAIACWWDREDC-FRVQLJSFSA-N

Experimental Spectra

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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Curcuma longa	KNApSAcK Database	22123792
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Penicillium sp. SA29	KNApSAcK Database	22123792

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents

Substituents

Glycinated bile acid
Trihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
7-hydroxysteroid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Cyclic alcohol
Secondary alcohol
Polyol
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboximidic acid
Monocarboxylic acid or derivatives
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Alcohol
Organonitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid glycine conjugate (CHEBI:17687 )
C26 bile acids, alcohols, and derivatives (C01921 )
Glycine conjugates (C01921 )
Cholane and derivatives (C01921 )
Glycine conjugates (LMST05030001 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	170 °C	Not Available
Boiling Point	692.04 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.0033 mg/mL	Not Available
LogP	1.65	Roda, A., Minutello, A., Angellotti, M. A., & Fini, A. (1990). Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. Journal of lipid research, 31(8), 1433-1443.

Predicted Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	1.38	ChemAxon
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-0.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.59 m³·mol⁻¹	ChemAxon
Polarizability	52.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000138

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Glycocholic_acid

METLIN ID

Not Available

PubChem Compound

10140

PDB ID

Not Available

ChEBI ID

17687

Good Scents ID

rw1608801

References

General References

Rius M, Nies AT, Hummel-Eisenbeiss J, Jedlitschky G, Keppler D: Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology. 2003 Aug;38(2):374-84. [PubMed:12883481 ]
Spiller RC, Frost PF, Stewart JS, Bloom SR, Silk DB: Delayed postprandial plasma bile acid response in coeliac patients with slow mouth-caecum transit. Clin Sci (Lond). 1987 Feb;72(2):217-23. [PubMed:3816078 ]
Matsui A, Psacharopoulos HT, Mowat AP, Portmann B, Murphy GM: Radioimmunoassay of serum glycocholic acid, standard laboratory tests of liver function and liver biopsy findings: comparative study of children with liver disease. J Clin Pathol. 1982 Sep;35(9):1011-7. [PubMed:7119120 ]
Marigold JH, Gilmore IT, Thompson RP: Effects of a meal on plasma clearance of [14C]glycocholic acid and indocyanine green in man. Clin Sci (Lond). 1981 Sep;61(3):325-30. [PubMed:7261553 ]
Xia S, Chen Z, Li L: [Relationship of vascular endothelial growth factor with bile acid in intrahepatic cholestasis of pregnancy]. Zhonghua Fu Chan Ke Za Zhi. 2002 Nov;37(11):669-71. [PubMed:12487922 ]
Li GY, Wang T, Huggins EM Jr, Shams NK, Davis JF, Calkins JH, Hornung CA, Altekruse JM, Sigel MM: Cholylglycine measured in serum by RIA and interleukin-1 beta determined by ELISA in differentiating viral hepatitis from chemical liver injury. J Occup Med. 1992 Sep;34(9):930-3. [PubMed:1447600 ]
de Franchis R, Vecchi M, Primignani M, Bonato C, Parravicini A, Cambieri R, Ciaci D, Annoni G: Diagnostic value of serum cholylglycine radioimmunoassay in chronic asymptomatic HBsAg carriers. Ric Clin Lab. 1983 Jul-Sep;13(3):301-5. [PubMed:6648236 ]
Xuan B, McClellan DA, Moore R, Chiou GC: Alternative delivery of insulin via eye drops. Diabetes Technol Ther. 2005 Oct;7(5):695-8. [PubMed:16241870 ]
Liss GM, Greenberg RA, Tamburro CH: Use of serum bile acids in the identification of vinyl chloride hepatotoxicity. Am J Med. 1985 Jan;78(1):68-76. [PubMed:3966491 ]
Rifai K, Ockenga J, Manns MP, Bischoff SC: Repeated administration of a vitamin preparation containing glycocholic acid in patients with hepatobiliary disease. Aliment Pharmacol Ther. 2006 May 1;23(9):1337-45. [PubMed:16629939 ]
Klapdor R: On the kinetics of glycocholate uptake and excretion by the normal and diseased liver in man. Hepatogastroenterology. 1981 Aug;28(4):189-91. [PubMed:7274980 ]
Friman S, Radberg G, Bosaeus I, Svanvik J: Hepatobiliary compensation for the loss of gallbladder function after cholecystectomy. An experimental study in the cat. Scand J Gastroenterol. 1990 Mar;25(3):307-14. [PubMed:2108486 ]
Bocharova LV, Tsodikov GV, Chernyshova NN, Kataev SS, Burkov SG: [Clinical value of determining serum levels of glycocholic acid in alcoholic lesions of the liver]. Klin Med (Mosk). 1992 Jul-Aug;70(7-8):41-4. [PubMed:1460824 ]
Murphy JL, Badaloo AV, Chambers B, Forrester TE, Wootton SA, Jackson AA: Maldigestion and malabsorption of dietary lipid during severe childhood malnutrition. Arch Dis Child. 2002 Dec;87(6):522-5. [PubMed:12456554 ]
Bremmelgaard A, Ranek L, Bahnsen M, Andreasen PB, Christensen E: Cholic acid conjugation test and quantitative liver function in acute liver failure. Scand J Gastroenterol. 1983 Sep;18(6):797-802. [PubMed:6669944 ]
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 ]
Kasatkin IuN, Vidiukov VI, Mironov SP, Chernyshova NN, Bocharova LV, Kataev SS: [Diagnosis of liver cirrhosis based on scintigraphic data and the level of cholylglycine in the blood serum]. Med Radiol (Mosk). 1989 Sep;34(9):8-12. [PubMed:2796646 ]
Collazos J, Mendarte U, De Miguel J: Clinical value of the determination of fasting glycocholic acid serum levels in patients with liver diseases. A comparison with standard liver tests. Gastroenterol Clin Biol. 1993;17(2):79-82. [PubMed:8500713 ]
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 ]

Showing NP-Card for Glycocholic acid (NP0000833)

MOL for NP0000833 (Glycocholic acid)

3D MOL for NP0000833 (Glycocholic acid)

3D SDF for NP0000833 (Glycocholic acid)

3D-SDF for NP0000833 (Glycocholic acid)

PDB for NP0000833 (Glycocholic acid)

3D PDB for NP0000833 (Glycocholic acid)

SMILES for NP0000833 (Glycocholic acid)

INCHI for NP0000833 (Glycocholic acid)

Structure for NP0000833 (Glycocholic acid)

3D Structure for NP0000833 (Glycocholic acid)