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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 UTC

HMDB ID

HMDB0000138

Secondary Accession Numbers

HMDB00138
HMDB0032596
HMDB31818
HMDB32596

Metabolite 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. Bacteroides, Bifidobacterium, Clostridium and Lactobacillus are involved in bile acid metabolism and produce glycocholic acid (PMID: 6265737 ; 10629797). 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
    0.7294   -0.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2230   -1.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2782    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4185    0.3176    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4661    2.1537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8100    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9249    0.9689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0297    1.7180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3737    1.2325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1221    2.6391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.0276   -2.5135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 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

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
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 33 76  1  0
M  END

  Mrv1652307301920072D          

 33 36  0  0  1  0            999 V2000
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    5.2782    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 20 11  1  0  0  0  0
 21 12  1  0  0  0  0
 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>
HMDB0000138

> <DATABASE_NAME>
hmdb

> <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 View Stereo Labels

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 Molecular Weight

465.6227

Monoisotopic Molecular Weight

465.309038113

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

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

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7119120)

Cell

Fibroblasts (HMDB: HMDB0000138)

Organ

Excreta

Biofluid or Excreta

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

Cellular substructure

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000138)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000138)

Source

Exogenous

Exogenous (HMDB: HMDB0000138)

Food

Food (HMDB: HMDB0000138)

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000138)

Animal

Animal (HMDB: HMDB0000138)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000138)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000138)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Disease pathway

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

Lipid metabolism pathway (HMDB: HMDB0000138)

Cellular process

Cell signaling (HMDB: HMDB0000138)

Biochemical process

Lipid transport (HMDB: HMDB0000138)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000138)

Molecular messenger

Signaling molecule (HMDB: HMDB0000138)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000138)

Pharmaceutical industry

Biomarker

Celiac disease (MarkerDB: MDB00000066)
Glycogen storage disease (MarkerDB: MDB00000066)
Alpha 1 Antitrypsin Deficiency (MarkerDB: MDB00000066)
Portal vein obstruction (MarkerDB: MDB00000066)
Hepatobiliary Diseases (MarkerDB: MDB00000066)
Chronic Active Hepatitis (MarkerDB: MDB00000066)
Intrahepatic Biliary Hypoplasia (MarkerDB: MDB00000066)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0033 mg/mL	Not Available
LogP	1.65	RODA,A ET AL. (1990)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	200.577	30932474
[M-H]-	Not Available	200.577	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000180

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	239.441	30932474
DeepCCS	[M+Na]+	213.419	30932474
AllCCS	[M+H]+	213.9	32859911
AllCCS	[M+H-H2O]+	212.3	32859911
AllCCS	[M+NH4]+	215.3	32859911
AllCCS	[M+Na]+	215.8	32859911
AllCCS	[M-H]-	207.6	32859911
AllCCS	[M+Na-2H]-	209.7	32859911
AllCCS	[M+HCOO]-	212.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycocholic acid	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	3709.2	Standard polar	33892256
Glycocholic acid	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	3812.5	Standard non polar	33892256
Glycocholic acid	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	4113.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycocholic acid,1TMS,isomer #1	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3929.3	Semi standard non polar	33892256
Glycocholic acid,1TMS,isomer #2	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3846.5	Semi standard non polar	33892256
Glycocholic acid,1TMS,isomer #3	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3737.8	Semi standard non polar	33892256
Glycocholic acid,1TMS,isomer #4	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3862.0	Semi standard non polar	33892256
Glycocholic acid,1TMS,isomer #5	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3813.0	Semi standard non polar	33892256
Glycocholic acid,2TMS,isomer #1	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3844.9	Semi standard non polar	33892256
Glycocholic acid,2TMS,isomer #10	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3750.8	Semi standard non polar	33892256
Glycocholic acid,2TMS,isomer #2	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3824.2	Semi standard non polar	33892256
Glycocholic acid,2TMS,isomer #3	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3864.3	Semi standard non polar	33892256
Glycocholic acid,2TMS,isomer #4	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3752.9	Semi standard non polar	33892256
Glycocholic acid,2TMS,isomer #5	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3778.6	Semi standard non polar	33892256
Glycocholic acid,2TMS,isomer #6	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3813.8	Semi standard non polar	33892256
Glycocholic acid,2TMS,isomer #7	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3699.5	Semi standard non polar	33892256
Glycocholic acid,2TMS,isomer #8	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3689.7	Semi standard non polar	33892256
Glycocholic acid,2TMS,isomer #9	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3705.2	Semi standard non polar	33892256
Glycocholic acid,3TMS,isomer #1	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	3770.7	Semi standard non polar	33892256
Glycocholic acid,3TMS,isomer #10	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3673.8	Semi standard non polar	33892256
Glycocholic acid,3TMS,isomer #2	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3782.3	Semi standard non polar	33892256
Glycocholic acid,3TMS,isomer #3	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3704.8	Semi standard non polar	33892256
Glycocholic acid,3TMS,isomer #4	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3751.2	Semi standard non polar	33892256
Glycocholic acid,3TMS,isomer #5	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3717.3	Semi standard non polar	33892256
Glycocholic acid,3TMS,isomer #6	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3725.3	Semi standard non polar	33892256
Glycocholic acid,3TMS,isomer #7	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3726.7	Semi standard non polar	33892256
Glycocholic acid,3TMS,isomer #8	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3692.0	Semi standard non polar	33892256
Glycocholic acid,3TMS,isomer #9	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3696.6	Semi standard non polar	33892256
Glycocholic acid,4TMS,isomer #1	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O	3709.6	Semi standard non polar	33892256
Glycocholic acid,4TMS,isomer #2	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C	3698.3	Semi standard non polar	33892256
Glycocholic acid,4TMS,isomer #3	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3699.3	Semi standard non polar	33892256
Glycocholic acid,4TMS,isomer #4	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3694.1	Semi standard non polar	33892256
Glycocholic acid,4TMS,isomer #5	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3701.3	Semi standard non polar	33892256
Glycocholic acid,5TMS,isomer #1	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C	3681.1	Semi standard non polar	33892256
Glycocholic acid,1TBDMS,isomer #1	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4125.5	Semi standard non polar	33892256
Glycocholic acid,1TBDMS,isomer #2	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4087.5	Semi standard non polar	33892256
Glycocholic acid,1TBDMS,isomer #3	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	3948.0	Semi standard non polar	33892256
Glycocholic acid,1TBDMS,isomer #4	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4070.6	Semi standard non polar	33892256
Glycocholic acid,1TBDMS,isomer #5	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4019.9	Semi standard non polar	33892256
Glycocholic acid,2TBDMS,isomer #1	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4265.2	Semi standard non polar	33892256
Glycocholic acid,2TBDMS,isomer #10	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4173.8	Semi standard non polar	33892256
Glycocholic acid,2TBDMS,isomer #2	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4234.1	Semi standard non polar	33892256
Glycocholic acid,2TBDMS,isomer #3	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4281.1	Semi standard non polar	33892256
Glycocholic acid,2TBDMS,isomer #4	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4153.8	Semi standard non polar	33892256
Glycocholic acid,2TBDMS,isomer #5	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4222.8	Semi standard non polar	33892256
Glycocholic acid,2TBDMS,isomer #6	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4259.0	Semi standard non polar	33892256
Glycocholic acid,2TBDMS,isomer #7	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4133.7	Semi standard non polar	33892256
Glycocholic acid,2TBDMS,isomer #8	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4126.9	Semi standard non polar	33892256
Glycocholic acid,2TBDMS,isomer #9	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4140.1	Semi standard non polar	33892256
Glycocholic acid,3TBDMS,isomer #1	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O	4376.4	Semi standard non polar	33892256
Glycocholic acid,3TBDMS,isomer #10	C[C@H](CCC(O)=NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4324.9	Semi standard non polar	33892256
Glycocholic acid,3TBDMS,isomer #2	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4404.3	Semi standard non polar	33892256
Glycocholic acid,3TBDMS,isomer #3	C[C@H](CCC(=NCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4296.6	Semi standard non polar	33892256
Glycocholic acid,3TBDMS,isomer #4	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4374.8	Semi standard non polar	33892256
Glycocholic acid,3TBDMS,isomer #5	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4326.7	Semi standard non polar	33892256
Glycocholic acid,3TBDMS,isomer #6	C[C@H](CCC(=NCC(=O)O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4330.4	Semi standard non polar	33892256
Glycocholic acid,3TBDMS,isomer #7	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O	4367.6	Semi standard non polar	33892256
Glycocholic acid,3TBDMS,isomer #8	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4321.3	Semi standard non polar	33892256
Glycocholic acid,3TBDMS,isomer #9	C[C@H](CCC(O)=NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C	4313.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_8) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-03di-0000900000-52e93813a9681b93b67c	2019-05-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-03k9-4000900000-79dfcaf6e620e89a8f51	2019-05-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-00di-9000000000-0153bf31bdc096136252	2019-05-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 40V, Negative-QTOF	splash10-00di-9000400000-e797c46f8e20c716b24c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 40V, Negative-QTOF	splash10-00di-9000200000-478282fdac3fd2f1d8a5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 20V, Negative-QTOF	splash10-03di-0000900000-ea860edeae64135340d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 40V, Negative-QTOF	splash10-00di-9000300000-9a12b83610eacbe64ab6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 10V, Negative-QTOF	splash10-03di-0000900000-54d1a3d9fa6179530909	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 20V, Negative-QTOF	splash10-03di-0000900000-e81f9c948a937824aad7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 10V, Negative-QTOF	splash10-03di-0000900000-7872961e706b0ce2acef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 10V, Positive-QTOF	splash10-03e9-0000900000-d2c234df86de685accab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 40V, Positive-QTOF	splash10-0a6r-3950000000-5e1c0bb11352c04bf6ab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 20V, Positive-QTOF	splash10-03di-1245900000-820e9f5a57e1ee8bcc05	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 20V, Positive-QTOF	splash10-03dr-0125900000-2a2d378bef3e5d7d7ef3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 35V, Positive-QTOF	splash10-03g0-2896300000-3561f6267f9465ea26a7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 35V, Positive-QTOF	splash10-092i-2896300000-a9ffe90b7ae4ed58097b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 40V, Positive-QTOF	splash10-06vi-2950000000-acdd4501d3673c8d4f18	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 10V, Positive-QTOF	splash10-03e9-0000900000-6e1ef68f12bc3fcd4183	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycocholic acid 10V, Positive-QTOF	splash10-01q9-0000900000-5010fdb018700f1ff637	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycocholic acid 10V, Positive-QTOF	splash10-00ea-5001900000-32dcdb2995334e0be0c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycocholic acid 20V, Positive-QTOF	splash10-00di-9001200000-efaede61ec6ea62b8f4b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycocholic acid 40V, Positive-QTOF	splash10-00di-9001000000-4a63863012ce5e7f9e89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycocholic acid 10V, Negative-QTOF	splash10-03dj-0000900000-e906f3d7308d2f341edc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycocholic acid 20V, Negative-QTOF	splash10-0h2b-2001900000-b325ccc2ef8a18eae690	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycocholic acid 40V, Negative-QTOF	splash10-00dl-9101100000-9cd953b22c5f0740b0bb	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2019-05-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2019-05-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Fibroblasts
Liver
Placenta
Prostate

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.06 +/- 0.04 uM	Adult (>18 years old)	Both	Normal	3816078	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.6(0.4-1.9) uM	Infant (0-1 year old)	Both	Normal	27163928	details
Blood	Detected and Quantified	0.88 +/- 0.26 uM	Children (1-13 years old)	Not Specified	Normal	7119120	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	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	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected and Quantified	10.15 +/- 7.51 nmol/g dry feces	Not Specified	Not Specified	Normal	22664055	details
Urine	Detected and Quantified	0.42 +/- 0.36 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	3944741	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.7 +/- 0.13 uM	Adult (>18 years old)	Both	Celiac Disease	3816078	details
Blood	Detected and Quantified	22 +/- 6 uM	Infant (0-1 year old)	Both	GI disorder	28521607	details
Blood	Detected and Quantified	16 +/- 5 uM	Infant (0-1 year old)	Both	GI disorder	28521607	details
Blood	Detected and Quantified	3.2 +/- 0.6 uM	Infant (0-1 year old)	Both	GI disorder	28521607	details
Blood	Detected and Quantified	1.4 +/- 0.4 uM	Infant (0-1 year old)	Both	GI disorder	28521607	details
Blood	Detected and Quantified	44.0 +/- 29.1 uM	Children (1-13 years old)	Not Specified	Extrahepatic biliary atresia (EHBA)	7119120	details
Blood	Detected and Quantified	14.8(5.2-25.3) uM	Infant (0-1 year old)	Both	Severe acute malnutrition	27163928	details
Blood	Detected and Quantified	8.4 +/- 8.7 uM	Children (1-13 years old)	Not Specified	Cholecohal cyst	7119120	details
Blood	Detected and Quantified	91.8 +/- 54.9 uM	Adult (>18 years old)	Not Specified	Intrahepatic biliary hypoplasia	7119120	details
Blood	Detected and Quantified	2.8 +/- 3.1 uM	Children (1-13 years old)	Not Specified	Idiopathic neonatal hepatitis	7119120	details
Blood	Detected and Quantified	25.9 +/- 24.0 uM	Children (1-13 years old)	Not Specified	Alpha-1-antitrypsin deficiency	7119120	details
Blood	Detected and Quantified	9.8 +/- 14.7 uM	Children (1-13 years old)	Not Specified	Cystic fibrosis	7119120	details
Blood	Detected and Quantified	2.9 +/- 2.4 uM	Children (1-13 years old)	Not Specified	Galactosemia	7119120	details
Blood	Detected and Quantified	14.5 +/- 16.1 uM	Children (1-13 years old)	Not Specified	Chronic active hepatitis	7119120	details
Blood	Detected and Quantified	8.6 +/- 7.9 uM	Children (1-13 years old)	Not Specified	Glycogen storage disease	7119120	details
Blood	Detected and Quantified	1.5 +/- 1.2 uM	Children (1-13 years old)	Not Specified	Fulminant hepatic failure	7119120	details
Blood	Detected and Quantified	10.5 +/- 13.1 uM	Children (1-13 years old)	Not Specified	Portal vein obstruction	7119120	details
Blood	Detected and Quantified	5.1 +/- 6.9 uM	Children (1-13 years old)	Not Specified	Wilson's disease	7119120	details
Blood	Detected and Quantified	43.6 +/- 11.8 uM	Adult (>18 years old)	Both	Hepatobiliary Disease	16629939	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Recurrent Clostridium difficile infection	24284963	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Recurrent Clostridium difficile infection	24284963	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	24284963	details

Associated Disorders and Diseases

Disease References

Hepatobiliary diseases
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 ]
Celiac disease
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 ]
Biliary atresia
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 ]
Choledochal cysts
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 ]
Intrahepatic biliary hypoplasia
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 ]
Neonatal hepatitis
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 ]
Alpha-1-antitrypsin deficiency
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 ]
Cystic fibrosis
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 ]
Galactosemia type 1
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 ]
Chronic active hepatitis
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 ]
Glycogen storage disease
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 ]
Acute liver failure
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 ]
Portal vein obstruction
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 ]
Wilson's disease
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 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] 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 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]

Associated OMIM IDs

212750 (Celiac disease)
210500 (Biliary atresia)
107400 (Alpha-1-antitrypsin deficiency)
219700 (Cystic fibrosis)
230400 (Galactosemia type 1)
277900 (Wilson's disease)
114500 (Colorectal cancer)
266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

GCHOLA

MarkerDB ID

MDB00000066

Good Scents ID

Not Available

References

Synthesis Reference

Cortese, Frank; Bauman, Louis. A synthesis of conjugated bile acids. I. Glycocholic acid. Journal of the American Chemical Society (1935), 57 1393-5.

Material Safety Data Sheet (MSDS)

Not Available

General References

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Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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 ]
Goto T, Myint KT, Sato K, Wada O, Kakiyama G, Iida T, Hishinuma T, Mano N, Goto J: LC/ESI-tandem mass spectrometric determination of bile acid 3-sulfates in human urine 3beta-Sulfooxy-12alpha-hydroxy-5beta-cholanoic acid is an abundant nonamidated sulfate. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):69-77. Epub 2006 Sep 1. [PubMed:16949895 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
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Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
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Enzymes

Enzyme Details

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

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

Reactions

Choloyl-CoA + Glycine → Coenzyme A + Glycocholic acid	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 Glycocholic acid (HMDB0000138)

MOL for HMDB0000138 (Glycocholic acid)

3D MOL for HMDB0000138 (Glycocholic acid)

3D SDF for HMDB0000138 (Glycocholic acid)

3D-SDF for HMDB0000138 (Glycocholic acid)

PDB for HMDB0000138 (Glycocholic acid)

3D PDB for HMDB0000138 (Glycocholic acid)

SMILES for HMDB0000138 (Glycocholic acid)

INCHI for HMDB0000138 (Glycocholic acid)

Structure for HMDB0000138 (Glycocholic acid)

3D Structure for HMDB0000138 (Glycocholic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions