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Record Information
Version1.0
Creation Date2016-07-13 19:41:27 UTC
Update Date2016-07-20 21:03:11 UTC
LmdbLMDB00058
Secondary Accession NumbersNone
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. 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 ).
Structure
Thumb
Synonyms
ValueSource
GlycocholateGenerator
3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycineHMDB
3a,7a,12a-Trihydroxy-5b-cholanic acid-24-glycineHMDB
3a,7a,12a-Trihydroxy-N-(carboxymethyl)-5b-cholan-24-amideHMDB
CholylglycineHMDB
Glycine cholateHMDB
Glycoreductodehydrocholic acidHMDB
GlycylcholateHMDB
Glycylcholic acidHMDB
N-(Carboxymethyl)-3a,7a,12a-trihydroxy-5b-cholan-24-amideHMDB
N-Choloyl-glycineHMDB
N-CholoylglycineHMDB
Glycocholic acid, sodium saltHMDB
Glycocholate sodiumHMDB
Chemical FormulaC26H43NO6
Average Molecular Weight465.6227
Monoisotopic Molecular Weight465.309038113
IUPAC Name2-[(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid
Traditional Name[(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid
CAS Registry Number475-31-0
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[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-MZMBZMQMSA-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
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Cyclic alcohol
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Polyol
  • Monocarboxylic acid or derivatives
  • 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 DescriptorsNot Available
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.7ALOGPS
logP1.38ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-0.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.09 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.59 m³·mol⁻¹ChemAxon
Polarizability53.03 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ds-0242900000-e424cae36874d8c9b014View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-5111349000-e192ab11f20a4e01e521View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-0000900000-52e93813a9681b93b67cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-03k9-4000900000-79dfcaf6e620e89a8f51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-0153bf31bdc096136252View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-1001900000-074a6139849914cbda16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-057j-9004800000-a7c2f5dbba8bf1c9944bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9104300000-1463dae6a363a87b8243View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0000900000-885c6e5d3f15b31df656View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h2b-3000900000-5c0d0e75172825307c79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9001000000-6241edfe03f378c4ba17View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Bile acid
  • Plasma
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Bile acidDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Pengcheng Zhou, J...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0000138
FooDB IDFDB012346
Phenol Explorer IDNot Available
KNApSAcK IDC00030410
BiGG ID38691
BioCyc IDNot Available
METLIN ID5169
PDB IDNot Available
Wikipedia LinkGlycocholic acid
Chemspider ID24747221
ChEBI ID29746
PubChem Compound ID23617285
Kegg Compound IDC01921
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [11316487 ]
  2. 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. [16037564 ]
  3. 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. [12576301 ]
  4. 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. [11907135 ]
  5. 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. [16949895 ]