Record Information
Version1.0
Creation date2012-01-13 17:26:30 UTC
Update date2018-05-28 20:05:20 UTC
Primary IDFDB029929
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNaringenin 4'-glucuronide
DescriptionNaringenin 4'-O-glucuronide belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid. Naringenin 4'-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number158196-35-1
Structure
Thumb
Synonyms
SynonymSource
(2S,3S,4S,5R,6S)-6-[4-(5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Naringenin 4'-glucuronidemanual
Naringenin 4'-O-glucuronidedb_source
Predicted Properties
PropertyValueSource
Water Solubility1.48 g/LALOGPS
logP0.73ALOGPS
logP0.89ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
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
Polarizability42.53 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O11
IUPAC name(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI IdentifierInChI=1S/C21H20O11/c22-9-5-11(23)15-12(24)7-13(31-14(15)6-9)8-1-3-10(4-2-8)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 KeyDFIUUCDSSKATFP-DNPGXZAYSA-N
Isomeric SMILESO[C@@H]1[C@@H](O)[C@H](OC2=CC=C(C=C2)C2CC(=O)C3=C(O2)C=C(O)C=C3O)O[C@@H]([C@H]1O)C(O)=O
Average Molecular Weight448.3769
Monoisotopic Molecular Weight448.100561482
Classification
Description belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-4p-o-glucuronide
  • Flavanone
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • Chromone
  • O-glycosyl compound
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Phenol ether
  • Aryl ketone
  • Phenoxy compound
  • Aryl alkyl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyran
  • Oxane
  • Benzenoid
  • Hydroxy acid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Foods

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
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 Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9127300000-c6835872bfd70e22889bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0uka-3062159000-c2aec4f11cbaea5cef50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ea-0290700000-5f5ea6b829455c17d870View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0490000000-4c70573c04a73fd85083View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmi-1930000000-008fa0b3097795aaf03aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fdk-1251900000-16bbf6f0839e8d3fc4c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2391200000-e011276b61a2b2625c86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-5590000000-4a1cbbb1494a41016d74View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41759
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 ID796
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference