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Bovine Metabolome Database



Showing metabocard for Glycocholic acid (BMDB00138)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:42
Accession Number BMDB00138
Common Name Glycocholic acid
Description Glycocholic acid is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID:16949895). More specifically, glycocholic acid or cholylglycine, is a crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. Its anion is called glycocholate. As the glycine conjugate of cholic acid, this compound acts as a detergent to solubilize fats for absorption and is itself absorbed. (PubChem). Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135)
Synonyms
  1. 3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine
  2. 3a,7a,12a-Trihydroxy-5b-cholanic acid-24-glycine
  3. 3a,7a,12a-Trihydroxy-N-(carboxymethyl)-5b-cholan-24-amide
  4. Cholylglycine
  5. Glycine cholate
  6. Glycocholate
  7. Glycocholic acid
  8. Glycoreductodehydrocholic acid
  9. Glycylcholate
  10. Glycylcholic acid
  11. N-(carboxymethyl)-3a,7a,12a-trihydroxy-5b-Cholan-24-amide
  12. N-Choloylglycine
  13. N-choloyl-Glycine
Chemical IUPAC Name 2-[4-(3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoylamino]acetic acid
Chemical Formula C26H43NO6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Bile Acids; Acyl Glycines
Sub Class
  • Bile-acid glycine conjugates
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; carboxylic acid; secondary carboxylic acid amide
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 465.623
Monoisotopic Molecular Weight 465.309052
Isomeric SMILES C[C@H](CCC(=O)NCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)CC4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
Canonical SMILES CC(CCC(=O)NCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C
KEGG Compound ID C01921 Link Image
BioCyc ID GLYCOCHOLIC_ACID Link Image
BiGG ID 38691 Link Image
Wikipedia Link Glycocholic acid Link Image
METLIN ID 5169 Link Image
PubChem Compound 439604 Link Image
PubChem Substance 5027 Link Image
ChEBI ID 29746 Link Image
CAS Registry Number 475-31-0
InChI Identifier InChI=1/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
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.
Melting Point (Experimental) 170 oC
Experimental Water Solubility 0.0033 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 0.0248 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity 1.65 [RODA,A ET AL. (1990)] Source: PhysProp
Predicted LogP/Hydrophobicity 1.70 [Predicted by ALOGPS]; 1.1 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID 1EIO Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
  • peroxisome
Biofluid Location Not Available
Tissue Location
Tissue References
Fibroblasts
Liver
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Bile Acid Biosynthesis
HMDB Pathways
Name Bile Acid Biosynthesis
Image Show Link Image
KEGG Pathways
Name Bile Acid Biosynthesis
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SimCell Pathways
Name Bile Acid Biosynthesis
Image Show Link Image
Graph
SBML
General References
  1. Wikipedia Link Image