Record Information
Version1.0
Creation date2011-09-21 00:23:03 UTC
Update date2015-07-21 06:57:28 UTC
Primary IDFDB022998
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-[(3a,5b,7b)-7-Hydroxy-24-oxo-3-(sulfooxy)cholan-24-yl]-glycine
DescriptionN-[(3a,5b,7b)-7-hydroxy-24-oxo-3-(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). Technically this compound is a sulfate conjugate of glycoursodeoxycholic acid. [HMDB]
CAS Number133429-88-6
Structure
Thumb
Synonyms
SynonymSource
4,6-Cholestadien-3-oneHMDB
4,6-Cholestadiene-3-oneHMDB
Cholest-4,6-dien-3-oneHMDB
Cholesta-4,6-diene-3-oneHMDB
Glycoursodeoxycholic acid 3-sulfateHMDB
Glycoursodeoxycholic acid 3-sulphateHMDB
2-{[(4R)-1-hydroxy-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentylidene]amino}acetateGenerator, HMDB
2-{[(4R)-1-hydroxy-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentylidene]amino}acetateGenerator, HMDB
2-{[(4R)-1-hydroxy-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentylidene]amino}acetic acidGenerator, HMDB
N-[(3a,5b,7b)-7-Hydroxy-24-oxo-3-(sulphooxy)cholan-24-yl]-glycineGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.0073 g/LALOGPS
logP0.21ALOGPS
logP1.13ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
pKa (Strongest Basic)-0.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.23 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity132.07 m³·mol⁻¹ChemAxon
Polarizability57.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H43NO8S
IUPAC name2-[(4R)-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid
InChI IdentifierInChI=1S/C26H43NO8S/c1-15(4-7-22(29)27-14-23(30)31)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(35-36(32,33)34)12-16(25)13-21(24)28/h15-21,24,28H,4-14H2,1-3H3,(H,27,29)(H,30,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1
InChI KeyDKXXSIJHWWVNMO-XROMFQGDSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O
Average Molecular Weight529.687
Monoisotopic Molecular Weight529.270938047
Classification
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Oxosteroid
  • 3-oxosteroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ly6-0385980000-5995781cc4339ad4d582JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-1120139000-3d45785e8f1a61602e52JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-9000560000-93ea0ff5e11728a73a46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000300000-cfa1998a277cdbf684f2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9001000000-2c832f31a929e04bba4fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1000490000-f9b2d5e70532870eb99cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-3000920000-7ab2abeb4e7f4e0c8853JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9202100000-4373117d5d9396949b98JSpectraViewer
ChemSpider ID19973535
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID21116917
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02409
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