Record Information
Version1.0
Creation date2010-04-08 22:12:34 UTC
Update date2020-02-24 19:11:06 UTC
Primary IDFDB016662
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKaempferol 4'-glucoside
Description3,5,7-trihydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4h-chromen-4-one 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. 3,5,7-trihydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 3,5,7-trihydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4h-chromen-4-one can be found in garden onion and sweet cherry, which makes 3,5,7-trihydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4h-chromen-4-one a potential biomarker for the consumption of these food products.
CAS Number52222-74-9
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.96 g/LALOGPS
logP0.41ALOGPS
logP0.19ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.03 m³·mol⁻¹ChemAxon
Polarizability43.23 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H20O11
IUPAC name3,5,7-trihydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-3-1-8(2-4-10)20-18(28)16(26)14-11(24)5-9(23)6-12(14)31-20/h1-6,13,15,17,19,21-25,27-29H,7H2
InChI KeyAUCGRWHWAGXNQS-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=CC=C(C=C2)C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)C(O)C(O)C1O
Average Molecular Weight448.3769
Monoisotopic Molecular Weight448.100561482
Classification
Description Belongs to the class of organic 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • Flavonoid-4p-o-glycoside
  • 3-hydroxyflavone
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Phenol ether
  • Phenoxy compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSKaempferol 4'-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f72-4730119000-aaebed34255fb2166db3Spectrum
Predicted GC-MSKaempferol 4'-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001r-7934600000-f4a5a67584dc14ba088dSpectrum
Predicted GC-MSKaempferol 4'-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0190700000-95f1e5e13fc376a43c612016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-f973f2bfbc7d15409cb42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-3590000000-2867e5f69069c563330f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1151900000-3d01cd19850d353794fc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1190200000-c3b76ae23db3368fe35b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3490000000-169606c403cf0770e9412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-9cd985e6b4b088698c7f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0510900000-ba46c8012f32a01faa4e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc0-2935100000-dd115822e4a266e458952021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-6cdaf2bc31caca882f1d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000900000-ee94b1a6148bf44667112021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxs-2910200000-2f6df8e2f48c6f45f68d2021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5491693
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFG98-E:KSH70-D
EAFUS IDNot Available
Dr. Duke IDKAEMPFEROL-4'-O-BETA-D-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00005152
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
Blackberry7.300 - 7.300 mg/100 g7.300 mg/100 g17896814
Garden onionExpected but not quantifiedNot AvailableKNAPSACK
Sweet cherryExpected but not quantifiedNot AvailableKNAPSACK
Showing 1 to 3 of 3 entries
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.