Showing metabocard for Glycocholic acid (BMDB0000138)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:20:03 UTC
Update Date2020-05-11 20:46:36 UTC
MCDB ID BMDB0000138
Secondary Accession Numbers
  • BMDB00138
Metabolite Identification
Common NameGlycocholic acid
DescriptionGlycocholic acid, also known as glycocholate or N-choloyl-glycine, 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. Glycocholic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glycocholic acid has been found to be associated with several diseases known as crohn's disease, hepatobiliary diseases, cystic fibrosis, and portal vein obstruction; also glycocholic acid has been linked to the inborn metabolic disorders including celiac disease.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 saltMeSH, HMDB
Glycocholate sodiumMeSH, HMDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0033 mg/mLNot Available
LogP1.65RODA,A ET AL. (1990)
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ds-0242900000-e424cae36874d8c9b0142017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-5111349000-e192ab11f20a4e01e5212017-10-06View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-0000900000-52e93813a9681b93b67c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-03k9-4000900000-79dfcaf6e620e89a8f512012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-0153bf31bdc0961362522012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-1001900000-074a6139849914cbda162017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-057j-9004800000-a7c2f5dbba8bf1c9944b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9104300000-1463dae6a363a87b82432017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0000900000-885c6e5d3f15b31df6562017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h2b-3000900000-5c0d0e75172825307c792017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9001000000-6241edfe03f378c4ba172017-09-01View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0032596
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012346
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlycocholic acid
METLIN IDNot Available
PubChem Compound23617285
PDB IDNot Available
ChEBI 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. Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]