Record Information
Version1.0
Creation date2011-09-21 00:23:36 UTC
Update date2015-07-21 06:57:29 UTC
Primary IDFDB023034
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSulfolithocholylglycine
DescriptionSulfolithocholylglycine 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). Sulfolithocholylglycine is a sulfated bile acids which has a greater renal clearance rate than lithocholylglycine. [HMDB]
CAS Number15324-64-8
Structure
Thumb
Synonyms
SynonymSource
SulpholithocholylglycineGenerator
2-{[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetateHMDB
2-{[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetateHMDB
2-{[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetic acidHMDB
GLCA-sulHMDB
Glycine amidatedHMDB
Glycolithocholate 3-sulfateHMDB
Glycolithocholate 3-sulphateHMDB
Glycolithocholate sulfateHMDB
Glycolithocholate sulphateHMDB
Glycolithocholic acid 3-sulfateHMDB
Glycolithocholic acid 3-sulphateHMDB
Glycolithocholic acid sulfateHMDB
Glycolithocholic acid sulphateHMDB
LCA-sulHMDB
SulfoglycolithocholateHMDB
Sulfoglycolithocholic acidHMDB
GLCA-Sulhmdb
glycine amidatedhmdb
glycolithocholate sulfatehmdb
LCA-Sulhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00038 g/LALOGPS
logP1.1ALOGPS
logP2.57ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area130 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.48 m³·mol⁻¹ChemAxon
Polarizability56.97 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H43NO7S
IUPAC name2-[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid
InChI IdentifierInChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17?,18+,19?,20?,21?,22?,25+,26-/m1/s1
InChI KeyFHXBAFXQVZOILS-JWOIRZCRSA-N
Isomeric SMILESC[C@H](CCC(=O)NCC(O)=O)C1CCC2C3CCC4C[C@H](CC[C@]4(C)C3CC[C@]12C)OS(O)(=O)=O
Average Molecular Weight513.687
Monoisotopic Molecular Weight513.276023425
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
  • Sulfated steroid skeleton
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Fatty acyl
  • Organic sulfuric acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

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-MSSulfolithocholylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053j-0114900000-d97f25a1a47de0f829f6Spectrum
Predicted GC-MSSulfolithocholylglycine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3012290000-9502bb51033c4fc4cf12Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000420000-10b258caeb33ced5ddeaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9001200000-96614f522a9de8596cb9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-dab61ff4b5c74608952bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1000790000-ae9e1f7f4d640ae84732Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03l0-3002910000-31acf45d89b477c1ac4aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9202100000-292763853bc057c7ee42Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC11301
Pubchem Compound ID53477756
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02639
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
Bile salt sulfotransferaseSULT2A1Q06520
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference