Hmdb loader

Showing metabocard for Glycocholic acid (HMDB0000138)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
enzymes (5) Show 5 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:48:59 UTC
HMDB IDHMDB0000138
Secondary Accession Numbers
  • HMDB00138
  • HMDB0032596
  • HMDB31818
  • HMDB32596
Metabolite Identification
Common NameGlycocholic acid
DescriptionGlycocholic 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
Data?1582752113
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000138 (Glycocholic acid)


  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
    4.7176    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3385   -3.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.2812    0.3114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5339   -1.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -3.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418    1.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1858    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7494    0.9421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0276   -2.5135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903    3.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -0.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512   -1.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430   -4.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.8161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  9  8  1  0  0  0  0
 14  1  1  1  0  0  0
 14  4  1  0  0  0  0
 15 10  1  6  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 16 10  1  0  0  0  0
 17  5  1  0  0  0  0
 17 14  1  1  0  0  0
 18  6  1  1  0  0  0
 19 12  1  1  0  0  0
 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
Download

3D MOL for HMDB0000138 (Glycocholic acid)

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
Download

3D SDF for HMDB0000138 (Glycocholic acid)


  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
    4.7176    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3385   -3.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.2812    0.3114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5339   -1.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -3.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418    1.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1858    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7494    0.9421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0276   -2.5135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903    3.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -0.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512   -1.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430   -4.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.8161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  9  8  1  0  0  0  0
 14  1  1  1  0  0  0
 14  4  1  0  0  0  0
 15 10  1  6  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 16 10  1  0  0  0  0
 17  5  1  0  0  0  0
 17 14  1  1  0  0  0
 18  6  1  1  0  0  0
 19 12  1  1  0  0  0
 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

$$$$
Download

3D-SDF for HMDB0000138 (Glycocholic acid)

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
Download

PDB for HMDB0000138 (Glycocholic acid)

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
Download

3D PDB for HMDB0000138 (Glycocholic acid)

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
Download

SMILES for HMDB0000138 (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
Download

INCHI for HMDB0000138 (Glycocholic acid)

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
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oylglycineChEBI
N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycineChEBI
N-CholoylglycineChEBI
3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycineGenerator
3Α,7α,12α-trihydroxy-5β-cholan-24-oylglycineGenerator
N-[(3a,5b,7a,12a)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycineGenerator
N-[(3Α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycineGenerator
GlycocholateGenerator
Glycine cholateHMDB
Glycocholic acid, sodium saltHMDB
CholylglycineHMDB
Glycocholate sodiumHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid-24-glycineHMDB
3alpha,7alpha,12alpha-Trihydroxy-N-(carboxymethyl)-5beta-cholan-24-amideHMDB
3Α,7α,12α-trihydroxy-5β-cholanic acid-24-glycineHMDB
3Α,7α,12α-trihydroxy-N-(carboxymethyl)-5β-cholan-24-amideHMDB
Glycoreductodehydrocholic acidHMDB
GlycylcholateHMDB
Glycylcholic acidHMDB
N-(Carboxymethyl)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-amideHMDB
N-(Carboxymethyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amideHMDB
N-Choloyl-glycineHMDB
Glycocholic acidHMDB
Chemical FormulaC26H43NO6
Average Molecular Weight465.6227
Monoisotopic Molecular Weight465.309038113
IUPAC Name2-[(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 Number475-31-0
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 KeyRFDAIACWWDREDC-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentGlycinated 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0033 mg/mLNot Available
LogP1.65RODA,A ET AL. (1990)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg200.57730932474
[M-H]-Not Available200.577http://allccs.zhulab.cn/database/detail?ID=AllCCS00000180
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP1.38ChemAxon
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-0.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.09 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.59 m³·mol⁻¹ChemAxon
Polarizability52.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-239.44130932474
DeepCCS[M+Na]+213.41930932474
AllCCS[M+H]+213.932859911
AllCCS[M+H-H2O]+212.332859911
AllCCS[M+NH4]+215.332859911
AllCCS[M+Na]+215.832859911
AllCCS[M-H]-207.632859911
AllCCS[M+Na-2H]-209.732859911
AllCCS[M+HCOO]-212.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glycocholic acidC[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@]12C3709.2Standard polar33892256
Glycocholic acidC[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@]12C3812.5Standard non polar33892256
Glycocholic acidC[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@]12C4113.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycocholic acid,1TMS,isomer #1C[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]3O3929.3Semi standard non polar33892256
Glycocholic acid,1TMS,isomer #2C[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]3O3846.5Semi standard non polar33892256
Glycocholic acid,1TMS,isomer #3C[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)C3737.8Semi standard non polar33892256
Glycocholic acid,1TMS,isomer #4C[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]3O3862.0Semi standard non polar33892256
Glycocholic acid,1TMS,isomer #5C[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]3O3813.0Semi standard non polar33892256
Glycocholic acid,2TMS,isomer #1C[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]3O3844.9Semi standard non polar33892256
Glycocholic acid,2TMS,isomer #10C[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]3O3750.8Semi standard non polar33892256
Glycocholic acid,2TMS,isomer #2C[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]3O3824.2Semi standard non polar33892256
Glycocholic acid,2TMS,isomer #3C[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]3O3864.3Semi standard non polar33892256
Glycocholic acid,2TMS,isomer #4C[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)C3752.9Semi standard non polar33892256
Glycocholic acid,2TMS,isomer #5C[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]3O3778.6Semi standard non polar33892256
Glycocholic acid,2TMS,isomer #6C[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]3O3813.8Semi standard non polar33892256
Glycocholic acid,2TMS,isomer #7C[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)C3699.5Semi standard non polar33892256
Glycocholic acid,2TMS,isomer #8C[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)C3689.7Semi standard non polar33892256
Glycocholic acid,2TMS,isomer #9C[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)C3705.2Semi standard non polar33892256
Glycocholic acid,3TMS,isomer #1C[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]3O3770.7Semi standard non polar33892256
Glycocholic acid,3TMS,isomer #10C[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)C3673.8Semi standard non polar33892256
Glycocholic acid,3TMS,isomer #2C[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]3O3782.3Semi standard non polar33892256
Glycocholic acid,3TMS,isomer #3C[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)C3704.8Semi standard non polar33892256
Glycocholic acid,3TMS,isomer #4C[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]3O3751.2Semi standard non polar33892256
Glycocholic acid,3TMS,isomer #5C[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)C3717.3Semi standard non polar33892256
Glycocholic acid,3TMS,isomer #6C[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)C3725.3Semi standard non polar33892256
Glycocholic acid,3TMS,isomer #7C[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]3O3726.7Semi standard non polar33892256
Glycocholic acid,3TMS,isomer #8C[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)C3692.0Semi standard non polar33892256
Glycocholic acid,3TMS,isomer #9C[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)C3696.6Semi standard non polar33892256
Glycocholic acid,4TMS,isomer #1C[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]3O3709.6Semi standard non polar33892256
Glycocholic acid,4TMS,isomer #2C[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)C3698.3Semi standard non polar33892256
Glycocholic acid,4TMS,isomer #3C[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)C3699.3Semi standard non polar33892256
Glycocholic acid,4TMS,isomer #4C[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)C3694.1Semi standard non polar33892256
Glycocholic acid,4TMS,isomer #5C[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)C3701.3Semi standard non polar33892256
Glycocholic acid,5TMS,isomer #1C[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)C3681.1Semi standard non polar33892256
Glycocholic acid,1TBDMS,isomer #1C[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]3O4125.5Semi standard non polar33892256
Glycocholic acid,1TBDMS,isomer #2C[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]3O4087.5Semi standard non polar33892256
Glycocholic acid,1TBDMS,isomer #3C[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)C3948.0Semi standard non polar33892256
Glycocholic acid,1TBDMS,isomer #4C[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]3O4070.6Semi standard non polar33892256
Glycocholic acid,1TBDMS,isomer #5C[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]3O4019.9Semi standard non polar33892256
Glycocholic acid,2TBDMS,isomer #1C[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]3O4265.2Semi standard non polar33892256
Glycocholic acid,2TBDMS,isomer #10C[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]3O4173.8Semi standard non polar33892256
Glycocholic acid,2TBDMS,isomer #2C[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]3O4234.1Semi standard non polar33892256
Glycocholic acid,2TBDMS,isomer #3C[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]3O4281.1Semi standard non polar33892256
Glycocholic acid,2TBDMS,isomer #4C[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)C4153.8Semi standard non polar33892256
Glycocholic acid,2TBDMS,isomer #5C[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]3O4222.8Semi standard non polar33892256
Glycocholic acid,2TBDMS,isomer #6C[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]3O4259.0Semi standard non polar33892256
Glycocholic acid,2TBDMS,isomer #7C[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)C4133.7Semi standard non polar33892256
Glycocholic acid,2TBDMS,isomer #8C[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)C4126.9Semi standard non polar33892256
Glycocholic acid,2TBDMS,isomer #9C[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)C4140.1Semi standard non polar33892256
Glycocholic acid,3TBDMS,isomer #1C[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]3O4376.4Semi standard non polar33892256
Glycocholic acid,3TBDMS,isomer #10C[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)C4324.9Semi standard non polar33892256
Glycocholic acid,3TBDMS,isomer #2C[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]3O4404.3Semi standard non polar33892256
Glycocholic acid,3TBDMS,isomer #3C[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)C4296.6Semi standard non polar33892256
Glycocholic acid,3TBDMS,isomer #4C[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]3O4374.8Semi standard non polar33892256
Glycocholic acid,3TBDMS,isomer #5C[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)C4326.7Semi standard non polar33892256
Glycocholic acid,3TBDMS,isomer #6C[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)C4330.4Semi standard non polar33892256
Glycocholic acid,3TBDMS,isomer #7C[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]3O4367.6Semi standard non polar33892256
Glycocholic acid,3TBDMS,isomer #8C[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)C4321.3Semi standard non polar33892256
Glycocholic acid,3TBDMS,isomer #9C[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)C4313.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycocholic acid GC-MS (TMS_3_8) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-03di-0000900000-52e93813a9681b93b67c2019-05-16HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-03k9-4000900000-79dfcaf6e620e89a8f512019-05-16HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-00di-9000000000-0153bf31bdc0961362522019-05-16HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 40V, Negative-QTOFsplash10-00di-9000400000-e797c46f8e20c716b24c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 40V, Negative-QTOFsplash10-00di-9000200000-478282fdac3fd2f1d8a52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 20V, Negative-QTOFsplash10-03di-0000900000-ea860edeae64135340d12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 40V, Negative-QTOFsplash10-00di-9000300000-9a12b83610eacbe64ab62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 10V, Negative-QTOFsplash10-03di-0000900000-54d1a3d9fa61795309092021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 20V, Negative-QTOFsplash10-03di-0000900000-e81f9c948a937824aad72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 10V, Negative-QTOFsplash10-03di-0000900000-7872961e706b0ce2acef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 10V, Positive-QTOFsplash10-03e9-0000900000-d2c234df86de685accab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 40V, Positive-QTOFsplash10-0a6r-3950000000-5e1c0bb11352c04bf6ab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 20V, Positive-QTOFsplash10-03di-1245900000-820e9f5a57e1ee8bcc052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 20V, Positive-QTOFsplash10-03dr-0125900000-2a2d378bef3e5d7d7ef32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 35V, Positive-QTOFsplash10-03g0-2896300000-3561f6267f9465ea26a72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 35V, Positive-QTOFsplash10-092i-2896300000-a9ffe90b7ae4ed58097b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 40V, Positive-QTOFsplash10-06vi-2950000000-acdd4501d3673c8d4f182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 10V, Positive-QTOFsplash10-03e9-0000900000-6e1ef68f12bc3fcd41832021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Glycocholic acid 10V, Positive-QTOFsplash10-01q9-0000900000-5010fdb018700f1ff6372021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycocholic acid 10V, Positive-QTOFsplash10-00ea-5001900000-32dcdb2995334e0be0c92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycocholic acid 20V, Positive-QTOFsplash10-00di-9001200000-efaede61ec6ea62b8f4b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycocholic acid 40V, Positive-QTOFsplash10-00di-9001000000-4a63863012ce5e7f9e892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycocholic acid 10V, Negative-QTOFsplash10-03dj-0000900000-e906f3d7308d2f341edc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycocholic acid 20V, Negative-QTOFsplash10-0h2b-2001900000-b325ccc2ef8a18eae6902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycocholic acid 40V, Negative-QTOFsplash10-00dl-9101100000-9cd953b22c5f0740b0bb2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2019-05-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2019-05-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Liver
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.06 +/- 0.04 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.6(0.4-1.9) uMInfant (0-1 year old)Both
Normal		 details
BloodDetected and Quantified0.88 +/- 0.26 uMChildren (1-13 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified10.15 +/- 7.51 nmol/g dry fecesNot SpecifiedNot Specified
Normal		 details
UrineDetected and Quantified0.42 +/- 0.36 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.7 +/- 0.13 uMAdult (>18 years old)BothCeliac Disease details
BloodDetected and Quantified22 +/- 6 uMInfant (0-1 year old)Both
GI disorder		 details
BloodDetected and Quantified16 +/- 5 uMInfant (0-1 year old)Both
GI disorder		 details
BloodDetected and Quantified3.2 +/- 0.6 uMInfant (0-1 year old)Both
GI disorder		 details
BloodDetected and Quantified1.4 +/- 0.4 uMInfant (0-1 year old)Both
GI disorder		 details
BloodDetected and Quantified44.0 +/- 29.1 uMChildren (1-13 years old)Not SpecifiedExtrahepatic biliary atresia (EHBA) details
BloodDetected and Quantified14.8(5.2-25.3) uMInfant (0-1 year old)Both
Severe acute malnutrition		 details
BloodDetected and Quantified8.4 +/- 8.7 uMChildren (1-13 years old)Not SpecifiedCholecohal cyst details
BloodDetected and Quantified91.8 +/- 54.9 uMAdult (>18 years old)Not SpecifiedIntrahepatic biliary hypoplasia details
BloodDetected and Quantified2.8 +/- 3.1 uMChildren (1-13 years old)Not Specified
Idiopathic neonatal hepatitis		 details
BloodDetected and Quantified25.9 +/- 24.0 uMChildren (1-13 years old)Not SpecifiedAlpha-1-antitrypsin deficiency details
BloodDetected and Quantified9.8 +/- 14.7 uMChildren (1-13 years old)Not SpecifiedCystic fibrosis details
BloodDetected and Quantified2.9 +/- 2.4 uMChildren (1-13 years old)Not SpecifiedGalactosemia details
BloodDetected and Quantified14.5 +/- 16.1 uMChildren (1-13 years old)Not SpecifiedChronic active hepatitis details
BloodDetected and Quantified8.6 +/- 7.9 uMChildren (1-13 years old)Not SpecifiedGlycogen storage disease details
BloodDetected and Quantified1.5 +/- 1.2 uMChildren (1-13 years old)Not Specified
Fulminant hepatic failure		 details
BloodDetected and Quantified10.5 +/- 13.1 uMChildren (1-13 years old)Not SpecifiedPortal vein obstruction details
BloodDetected and Quantified5.1 +/- 6.9 uMChildren (1-13 years old)Not SpecifiedWilson's disease details
BloodDetected and Quantified43.6 +/- 11.8 uMAdult (>18 years old)BothHepatobiliary Disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCCD details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIleal Crohn's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Recurrent Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Recurrent Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothClostridium difficile infection details
Associated Disorders and Diseases
Disease References
Hepatobiliary diseases
  1. 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
  1. 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
  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 ]
Choledochal cysts
  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 ]
Intrahepatic biliary hypoplasia
  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 ]
Neonatal hepatitis
  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 ]
Alpha-1-antitrypsin deficiency
  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 ]
Cystic fibrosis
  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 ]
Galactosemia type 1
  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
  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 ]
Glycogen storage disease
  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 ]
Acute liver failure
  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 ]
Portal vein obstruction
  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 ]
Wilson's disease
  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 ]
Colorectal cancer
  1. 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 ]
  2. 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 ]
  3. 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
  1. 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
  1. 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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012346
KNApSAcK IDC00030410
Chemspider ID9734
KEGG Compound IDC01921
BioCyc IDGLYCOCHOLIC_ACID
BiGG IDNot Available
Wikipedia LinkGlycocholic_acid
METLIN IDNot Available
PubChem Compound10140
PDB IDNot Available
ChEBI ID17687
Food Biomarker OntologyNot Available
VMH IDGCHOLA
MarkerDB IDMDB00000066
Good Scents IDNot Available
References
Synthesis ReferenceCortese, 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)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]
  21. 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 ]
  22. 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 ]
  23. 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 ]
  24. 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 ]
  25. 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 ]
  26. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  27. 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 ]
  28. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  29. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  30. Masuda N: Deconjugation of bile salts by Bacteroids and Clostridium. Microbiol Immunol. 1981;25(1):1-11. [PubMed:6265737 ]
  31. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  32. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  33. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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 aciddetails
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