Record Information
Version1.0
Creation date2011-09-21 00:23:39 UTC
Update date2015-07-21 06:57:29 UTC
Primary IDFDB023038
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine
DescriptionN-[(3a,5b,7a,12a)-3,7-dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-Glycine 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) [HMDB]
CAS Number74723-17-4
Structure
Thumb
Synonyms
SynonymSource
N-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulphooxy)cholan-24-yl]-glycineGenerator
Cholane glycine derivativeHMDB
2-{[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetateHMDB
2-{[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetateHMDB
2-{[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetic acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP-0.22ALOGPS
logP0.031ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)-1.2ChemAxon
pKa (Strongest Basic)-0.24ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.46 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity133.58 m³·mol⁻¹ChemAxon
Polarizability57.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H43NO9S
IUPAC name2-[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,9-dihydroxy-2,15-dimethyl-16-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid
InChI IdentifierInChI=1S/C26H43NO9S/c1-14(4-7-22(30)27-13-23(31)32)17-5-6-18-24-19(12-21(26(17,18)3)36-37(33,34)35)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-29H,4-13H2,1-3H3,(H,27,30)(H,31,32)(H,33,34,35)/t14-,15+,16-,17-,18?,19?,20-,21+,24?,25+,26-/m1/s1
InChI KeyJZLKXIMBAHDSBJ-NLKBZSSJSA-N
Isomeric SMILES[H][C@@]12C[C@H](O)CC[C@]1(C)C1C[C@H](OS(O)(=O)=O)[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O
Average Molecular Weight545.686
Monoisotopic Molecular Weight545.265852669
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
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • Sulfated steroid skeleton
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Fatty acyl
  • Sulfate-ester
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Alkyl sulfate
  • N-acyl-amine
  • Fatty amide
  • Organic sulfuric acid or derivatives
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ul9-1312590000-e6e12f3b85e0c449c978Spectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-2110129000-0629110aa01dadcab2f8Spectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, "N-[(3a,5b,7a,12a)-3,7-dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-Glycine,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,7-Dihydroxy-24-oxo-12-(sulfooxy)cholan-24-yl]-glycine, TMS_3_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2000490000-27e70761b1de239308f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-6000920000-b8d7b7596079569e926eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9202510000-b31c379899e79ca961f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0000290000-f5afc42d6a3480129a02Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006t-3000930000-19c707086f28600fedc7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9101100000-d3c88f9e9fa504ae77cdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-713bdd24bb7acc520f16Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-1000290000-ab46ce9e532092ee6b89Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000320000-d002e53e6d9cad951dcdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0000970000-4331cf298db116eac8f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002g-4234890000-7f13629b87fe8ef6af4bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9310000000-603cf2a89adfa3c5bd33Spectrum
NMRNot Available
ChemSpider ID13628380
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID21252319
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02644
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
Glycine N-acyltransferase-like protein 3GLYATL3Q5SZD4
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference