Record Information
Version1.0
Creation date2010-04-08 22:10:07 UTC
Update date2019-11-26 03:06:36 UTC
Primary IDFDB012346
Secondary Accession Numbers
  • FDB010533
Chemical Information
FooDB NameGlycocholic acid
DescriptionGlycocholic acid, also known as N-choloylglycine or glycocholate, 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 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number475-31-0
Structure
Thumb
Synonyms
SynonymSource
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
3a,7a,12a-Trihydroxy-5b-cholanic acid-24-glycineHMDB
3a,7a,12a-Trihydroxy-N-(carboxymethyl)-5b-cholan-24-amideHMDB
N-(Carboxymethyl)-3a,7a,12a-trihydroxy-5b-cholan-24-amideHMDB
Predicted Properties
PropertyValueSource
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
Chemical FormulaC26H43NO6
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
InChI IdentifierInChI=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)
InChI KeyRFDAIACWWDREDC-UHFFFAOYSA-N
Isomeric SMILESCC(CCC(=O)NCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C
Average Molecular Weight465.6227
Monoisotopic Molecular Weight465.309038113
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 67.07%; H 9.31%; N 3.01%; O 20.62%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]13D +27.8 (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_3_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-0000900000-52e93813a9681b93b67cSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-03k9-4000900000-79dfcaf6e620e89a8f51Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-0153bf31bdc096136252Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000400000-e797c46f8e20c716b24cSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000200000-478282fdac3fd2f1d8a5Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-ea860edeae64135340d1Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000300000-9a12b83610eacbe64ab6Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-54d1a3d9fa6179530909Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-e81f9c948a937824aad7Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-7872961e706b0ce2acefSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0000900000-d2c234df86de685accabSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3950000000-5e1c0bb11352c04bf6abSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-1245900000-820e9f5a57e1ee8bcc05Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03dr-0125900000-2a2d378bef3e5d7d7ef3Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03g0-2896300000-3561f6267f9465ea26a7Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-092i-2896300000-a9ffe90b7ae4ed58097bSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-06vi-2950000000-acdd4501d3673c8d4f18Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0000900000-6e1ef68f12bc3fcd4183Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0000900000-5010fdb018700f1ff637Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ea-5001900000-32dcdb2995334e0be0c9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9001200000-efaede61ec6ea62b8f4bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9001000000-4a63863012ce5e7f9e89Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0000900000-e906f3d7308d2f341edcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h2b-2001900000-b325ccc2ef8a18eae690Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9101100000-9cd953b22c5f0740b0bbSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID24747221
ChEMBL IDNot Available
KEGG Compound IDC01921
Pubchem Compound ID23617285
Pubchem Substance IDNot Available
ChEBI ID17687
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00138
CRC / DFC (Dictionary of Food Compounds) IDHGM07-B:HGM07-B
EAFUS ID1528
Dr. Duke IDNot Available
BIGG ID38691
KNApSAcK IDC00030410
HET ID1EIO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGlycocholic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine N-acyltransferaseGLYATQ6IB77
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Glycine N-acyltransferase-like protein 3GLYATL3Q5SZD4
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference