Record Information
Version1.0
Creation date2010-04-08 22:06:06 UTC
Update date2019-11-26 02:59:50 UTC
Primary IDFDB004135
Secondary Accession Numbers
  • FDB004792
Chemical Information
FooDB NameKaempferol 3-O-beta-D-galactopyranoside
DescriptionKaempferol 3-o-beta-d-galactopyranoside, also known as trifolin or trifolioside, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-o-beta-d-galactopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 3-o-beta-d-galactopyranoside can be found in horseradish, which makes kaempferol 3-o-beta-d-galactopyranoside a potential biomarker for the consumption of this food product.
CAS Number23627-87-4
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP0.52ALOGPS
logP0.16ChemAxon
logS-2.4ALOGPS
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
Polarizability42.47 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H20O11
IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5R,6R)-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/t13-,15+,17+,18-,21+/m1/s1
InChI KeyJPUKWEQWGBDDQB-DTGCRPNFSA-N
Isomeric SMILESOC[C@H]1O[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O
Average Molecular Weight448.3769
Monoisotopic Molecular Weight448.100561482
Classification
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentPyranones and derivatives
Alternative Parents
Substituents
  • Alkyl aryl ether
  • Pyranone
  • Heteroaromatic compound
  • Vinylogous ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • 1,2-diol
  • Lactone
  • Secondary alcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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-MSKaempferol 3-O-beta-D-galactopyranoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSKaempferol 3-O-beta-D-galactopyranoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0190800000-d3b297eb0fe481caa10a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-1e520254d0769f8f845e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-3590000000-7f6360b543570fc557162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1151900000-879fdf0c200d1a8caf5b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1190200000-8b8be60a1a225937d8d82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3590000000-22efe60043282fcdf3792016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090200000-706a2cc703dc724225bc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000k-0090900000-437e416a439402c510ac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-03ec6f5113b2bb58d5cf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-84741e5bcc8a2704c4e52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0050900000-bcc3a3527efd34a156562021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-d4a9b7661844b5b3c3082021-09-24View 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 IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID3-O-(BETA-D-GALACTOPYRANOSYL)-KAEMPFEROL
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
HorseradishExpected but not quantifiedNot AvailableDUKE
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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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).