Naringenin 7-glucuronide (CHEM041632)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:35:51 UTC
Update Date2016-11-09 01:22:30 UTC
Accession NumberCHEM041632
Identification
Common NameNaringenin 7-glucuronide
ClassSmall Molecule
DescriptionA dihydroxyflavanone that is naringenin in which the phenolic hydrogen at position 7 has been replaced by a beta-D-glucuronosyl residue.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Naringenin-7-O-glucuronideChEBI
Naringenin 7-O-b-D-glucuronideHMDB
Naringenin 7-O-β-D-glucuronideHMDB
Chemical FormulaC21H20O11
Average Molecular Mass448.377 g/mol
Monoisotopic Mass448.101 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid
SMILESO[C@@H]1[C@@H](O)[C@H](OC2=CC3=C(C(=O)CC(O3)C3=CC=C(O)C=C3)C(O)=C2)O[C@@H]([C@H]1O)C(O)=O
InChI IdentifierInChI=1S/C21H20O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-6,13,16-19,21-23,25-27H,7H2,(H,28,29)/t13?,16-,17-,18+,19-,21+/m0/s1
InChI KeyBDCRTIDKZGEVEN-DNPGXZAYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-7-o-glucuronide
  • Flavonoid-7-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavanone
  • Flavan
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Aryl alkyl ketone
  • Aryl ketone
  • Beta-hydroxy acid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Acetal
  • Ether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.69 g/LALOGPS
logP0.65ALOGPS
logP0.89ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)2.73ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.3 m³·mol⁻¹ChemAxon
Polarizability42.8 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bu0-9115200000-27930d7f2fd2eddf6aacSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0uka-3052159000-5d490fdaf0482a20428fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-0290800000-3da4a859883de613b687Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0590000000-613216cc5c3eac68ea8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1930000000-d1f549dd4279146b7de9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fdk-1150900000-027d3f65b286af3eb6f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2291200000-c647c7d9e0919e700f80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4490000000-e9e9241434a5ed69a0ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0030900000-9099ae6cceec31e27e6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-0190700000-32bd1c30a5eaea8d8881Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-0970200000-59bc4407439899017b5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dj-0090500000-01e33ad94c06b74ac17bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190000000-5be014833fa610089e5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-0890000000-2b7570a316bc5cbaab9fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041761
FooDB IDFDB029931
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID29341798
ChEBI ID132835
PubChem Compound ID51136360
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.