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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2019-10-07 16:30:03 UTC
Update Date2019-10-16 15:41:00 UTC
HMDB IDHMDB0240433
Secondary Accession NumbersNone
Metabolite Identification
Common NameEnterolactone 3''-glucuronide
DescriptionEnterolactone 3''-glucuronide is a lignan metabolite produced in the liver. Enterolactone glucuronide is a potential urinary biomarker of whole grain intake (PMID: 23307617 ).
Structure
Data?1570466284
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(3-{[(3S,4S)-4-[(3-hydroxyphenyl)methyl]-5-oxooxolan-3-yl]methyl}phenoxy)oxane-2-carboxylateHMDB
Enterolactone 3’’-glucuronideHMDB
Enterolactone glucuronideHMDB
Enterolactone monoglucuronideHMDB
Enterolactone 3''-glucuronideHMDB
Chemical FormulaC24H26O10
Average Molecular Weight474.462
Monoisotopic Molecular Weight474.152597037
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3-{[(3S,4S)-4-[(3-hydroxyphenyl)methyl]-5-oxooxolan-3-yl]methyl}phenoxy)oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3-{[(3S,4S)-4-[(3-hydroxyphenyl)methyl]-5-oxooxolan-3-yl]methyl}phenoxy)oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)[C@H](OC2=CC=CC(C[C@@H]3COC(=O)[C@H]3CC3=CC(O)=CC=C3)=C2)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C24H26O10/c25-15-5-1-3-13(8-15)10-17-14(11-32-23(17)31)7-12-4-2-6-16(9-12)33-24-20(28)18(26)19(27)21(34-24)22(29)30/h1-6,8-9,14,17-21,24-28H,7,10-11H2,(H,29,30)/t14-,17+,18+,19+,20-,21+,24-/m1/s1
InChI KeyYPASCVZALRQWQG-NBSJFAFNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Hydroxy fatty acid
  • Branched fatty acid
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.54ALOGPS
logP1.66ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.98 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity114.72 m³·mol⁻¹ChemAxon
Polarizability46.78 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093696
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bondia-Pons I, Barri T, Hanhineva K, Juntunen K, Dragsted LO, Mykkanen H, Poutanen K: UPLC-QTOF/MS metabolic profiling unveils urinary changes in humans after a whole grain rye versus refined wheat bread intervention. Mol Nutr Food Res. 2013 Mar;57(3):412-22. doi: 10.1002/mnfr.201200571. Epub 2013 Jan 10. [PubMed:23307617 ]