Record Information
Version1.0
Creation date2010-04-08 22:05:32 UTC
Update date2019-11-26 02:58:01 UTC
Primary IDFDB002824
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKaempferol 3-galactoside
DescriptionKaempferol 3-galactoside belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-galactoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Kaempferol 3-galactoside is found, on average, in the highest concentration within a few different foods, such as tea, common grapes, and almonds. Kaempferol 3-galactoside has also been detected, but not quantified in, several different foods, such as white lupines, peachs, horseradish, caraway, and star anises. This could make kaempferol 3-galactoside a potential biomarker for the consumption of these foods.
CAS Number23627-87-4
Structure
Thumb
Synonyms
SynonymSource
3-O-b-D-Galactopyranosyloxy-4',5,7-trihydroxyflavonedb_source
Kaempferol 3-galactosidedb_source
Kaempferol 3-O-beta-D-galactosidebiospider
Kaempferol-3-O-galactosidebiospider
Trifoliosidedb_source
Predicted Properties
PropertyValueSource
logP0.16ChemAxon
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.29 m³·mol⁻¹ChemAxon
Polarizability42.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O11
IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,4S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2
InChI KeyJPUKWEQWGBDDQB-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)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-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.25%; H 4.50%; O 39.25%DFC
Melting PointMp 235° (229-231°)DFC
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
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5488283
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID316
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNT95-D:CNT95-D
EAFUS IDNot Available
Dr. Duke IDKAEMPFEROL-3-O-GALACTOSIDE|TRIFOLIN
BIGG IDNot Available
KNApSAcK IDC00005137
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— 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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.