Record Information
Version1.0
Creation date2011-09-21 00:23:37 UTC
Update date2015-07-21 06:57:29 UTC
Primary IDFDB023035
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine
DescriptionN-[(3a,5b,7a,12a)-3,12-dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine is an acyl glycine and a sulfated 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). As a bile acid sulfate, N-[(3a,5b,7a,12a)-3,12-dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine is typically found in urine. These conjugates are formed as a part of detoxification of endogenous and exogenous components in the body (PMID:3584362). [HMDB]
CAS Number71977-73-6
Structure
Thumb
Synonyms
SynonymSource
N-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulphooxy)cholan-24-yl]-glycineGenerator
2-{[(4R)-4-[(2S,5R,7S,9R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyl-9-(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)-5,16-dihydroxy-2,15-dimethyl-9-(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)-5,16-dihydroxy-2,15-dimethyl-9-(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-0.19ALOGPS
logP0.059ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)-1.1ChemAxon
pKa (Strongest Basic)-0.13ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.46 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity133.58 m³·mol⁻¹ChemAxon
Polarizability58.04 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)-5,16-dihydroxy-2,15-dimethyl-9-(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(29)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)36-37(33,34)35/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 KeyBJPPZTDOLXZUSK-NLKBZSSJSA-N
Isomeric SMILES[H][C@@]12C[C@H](O)CC[C@]1(C)C1C[C@H](O)[C@]3(C)[C@H](CCC3C1[C@@H](C2)OS(O)(=O)=O)[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
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Sulfate-ester
  • Sulfuric acid monoester
  • Fatty acyl
  • Fatty amide
  • Sulfuric acid ester
  • Alkyl sulfate
  • N-acyl-amine
  • Cyclic alcohol
  • Organic sulfuric acid or derivatives
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • 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)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gl9-1231490000-253283480a4fc4a47a7bSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-2110129000-a9dfafcc5584b8686bafSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, "N-[(3a,5b,7a,12a)-3,12-dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-[(3a,5b,7a,12a)-3,12-Dihydroxy-24-oxo-7-(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-2000490000-2e8d2cfb1348e6d760d3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-6000920000-cca4d584b697cef683ebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9002400000-b0343d0969f16bb3a4f6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0000290000-f5afc42d6a3480129a02Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3000930000-f62f0db1db3c100bce9dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9101100000-fbc092ad5516e9401161Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-fee96f51477bba0d1d44Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-2000290000-1a2b57c158397d0e4193Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000320000-8a28de6f794a57ce1524Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0000090000-6b6a2f9cd994ee7fd4bbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fv-6413490000-b5b0edeb8a2748d05391Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9301100000-bfb0977d7351d65bda46Spectrum
NMRNot Available
ChemSpider ID13628378
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID21252317
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02640
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