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Showing Compound Glycocholic acid (FDB012346)

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
MOLSDFPDBSMILESInChI
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-0000900000-52e93813a9681b93b67c2019-05-16View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-03k9-4000900000-79dfcaf6e620e89a8f512019-05-16View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00di-9000000000-0153bf31bdc0961362522019-05-16View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000400000-e797c46f8e20c716b24c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000200000-478282fdac3fd2f1d8a52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-ea860edeae64135340d12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000300000-9a12b83610eacbe64ab62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-54d1a3d9fa61795309092021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-e81f9c948a937824aad72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-7872961e706b0ce2acef2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0000900000-d2c234df86de685accab2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3950000000-5e1c0bb11352c04bf6ab2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-1245900000-820e9f5a57e1ee8bcc052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03dr-0125900000-2a2d378bef3e5d7d7ef32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03g0-2896300000-3561f6267f9465ea26a72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-092i-2896300000-a9ffe90b7ae4ed58097b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-06vi-2950000000-acdd4501d3673c8d4f182021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0000900000-6e1ef68f12bc3fcd41832021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0000900000-5010fdb018700f1ff6372021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ea-5001900000-32dcdb2995334e0be0c92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9001200000-efaede61ec6ea62b8f4b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9001000000-4a63863012ce5e7f9e892016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0000900000-e906f3d7308d2f341edc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h2b-2001900000-b325ccc2ef8a18eae6902016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9101100000-9cd953b22c5f0740b0bb2016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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