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Showing Compound Naringenin 4'-glucoside (FDB021742)

Record Information
Version1.0
Creation date2011-03-17 23:28:37 UTC
Update date2019-11-26 03:20:50 UTC
Primary IDFDB021742
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNaringenin 4'-glucoside
DescriptionNaringenin 4'-glucoside is a member of the class of compounds known as flavonoid o-glycosides. Flavonoid o-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Naringenin 4'-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Naringenin 4'-glucoside can be found in grapefruit/pummelo hybrid, which makes naringenin 4'-glucoside a potential biomarker for the consumption of this food product.
CAS Number81202-36-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.3 g/LALOGPS
logP0.21ALOGPS
logP0.57ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)7.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.43 m³·mol⁻¹ChemAxon
Polarizability42.83 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H22O10
IUPAC name5,7-dihydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-3-1-9(2-4-11)14-7-13(25)17-12(24)5-10(23)6-15(17)30-14/h1-6,14,16,18-24,26-28H,7-8H2
InChI KeyKSDSYIXRWHRPMN-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=CC=C(C=C2)C2CC(=O)C3=C(O)C=C(O)C=C3O2)C(O)C(O)C1O
Average Molecular Weight434.397
Monoisotopic Molecular Weight434.121296908
Classification
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Oxacycle
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNaringenin 4'-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g4i-8934500000-3b6b8af00c21af5720a8Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00y0-0290500000-09327a9783d2f624f16f2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0590000000-a4b6f57c857b541eb27c2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmi-1930000000-4f6af7f7522f0d7bb46a2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-1260900000-e68203b337b828d8ceee2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1390100000-8150ec61de9f1682b34d2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fkc-5590000000-65b45fadf0987df315f12017-06-28View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID216
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFM77-B:MNV80-L
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
Processing...
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— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.