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Record Information
Version4.0
Creation Date2012-09-12 03:41:39 UTC
Update Date2017-09-22 16:40:23 UTC
HMDB IDHMDB0041768
Secondary Accession Numbers
  • HMDB41768
StatusExpected but not Quantified
Metabolite Identification
Common NamePhloretin 2'-O-glucuronide
DescriptionPhloretin 2'-O-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ). Phloretin glucuronide is a biomarker for the consumption of apples
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H22O11
Average Molecular Weight450.3928
Monoisotopic Molecular Weight450.116211546
IUPAC Name(2S,3S,4S,5R,6S)-6-{3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)[C@H](OC2=CC(O)=CC(O)=C2C(=O)CCC2=CC=C(O)C=C2)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C21H22O11/c22-10-4-1-9(2-5-10)3-6-12(24)15-13(25)7-11(23)8-14(15)31-21-18(28)16(26)17(27)19(32-21)20(29)30/h1-2,4-5,7-8,16-19,21-23,25-28H,3,6H2,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
InChI KeyYFJJAJIWPWXWJJ-ZFORQUDYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as flavonoid o-glycosides. These are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassFlavonoids
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • 2'-hydroxy-dihydrochalcone
  • Phenolic glycoside
  • Linear 1,3-diarylpropanoid
  • Cinnamylphenol
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Alkyl-phenylketone
  • Hexose monosaccharide
  • Butyrophenone
  • Glycosyl compound
  • O-glycosyl compound
  • Phenylketone
  • Benzoyl
  • Phenoxy compound
  • Phenol ether
  • Resorcinol
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Pyran
  • Hydroxy acid
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition
Biological Location:
Source:
Subcellular:
Biofluid and excreta:
Organ and components:
Role
Biological role:
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
Water Solubility1.47 mg/mLALOGPS
logP1.4ALOGPS
logP1.3ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.82ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area194.21 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.72 m3·mol-1ChemAxon
Polarizability42.33 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 762 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 762 details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 762 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 762 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID762
FoodDB IDFDB029939
KNApSAcK IDNot Available
Chemspider ID8065632
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0041768
METLIN IDNot Available
PubChem Compound9889961
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]