Show more...Show more...Show more...Show more...
Record Information
Version2.0
Created at2007-01-22 22:44:31 UTC
Updated at2025-02-11 15:46:22 UTC
NP-MRD IDNP0000460
Natural Product DOIhttps://doi.org/10.57994/0396
Secondary Accession NumbersNone
Natural Product Identification
Common NameKaempferol
DescriptionKaempferol, also known as rhamnolutein or c.I. 75640, Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, kaempferol is considered to be a flavonoid molecule. A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4'. Kaempferol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Kaempferol exists in all eukaryotes, ranging from yeast to humans. Kaempferol is a bitter tasting compound. Kaempferol is found, on average, in the highest concentration within a few different foods, such as saffrons, capers, and cumins and in a lower concentration in lovages, endives, and cloves. Kaempferol has also been detected, but not quantified, in several different foods, such as shallots, pine nuts, feijoa, kombus, and chicory leaves. This could make kaempferol a potential biomarker for the consumption of these foods. Kaempferol is a potentially toxic compound.
Structure
Thumb
Synonyms
Chemical FormulaC15H10O6
Average Mass286.2363 Da
Monoisotopic Mass286.04774 Da
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Namekaempferol
CAS Registry Number520-18-3
SMILES
OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C=C2O
InChI Identifier
InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H
InChI KeyIYRMWMYZSQPJKC-UHFFFAOYSA-N
Experimental Spectra
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500.2, CD3OD, simulated)lpecio@iung.pulawy.plNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-16View Spectrum
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point285 - 287 °CNot Available
Boiling Point582.00 to 583.00 °C. @ 860.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1191 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.685 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP1.99ALOGPS
logP2.46ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.88 m³·mol⁻¹ChemAxon
Polarizability27.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0005801
DrugBank IDDB01852
Phenol Explorer Compound ID290
FoodDB IDFDB000633
KNApSAcK IDC00004565
Chemspider ID4444395
KEGG Compound IDC05903
BioCyc IDCPD1F-90
BiGG IDNot Available
Wikipedia Linkkaempferol
METLIN IDNot Available
PubChem Compound5280863
PDB IDKMP
ChEBI ID28499
Good Scents IDrw1588991
References
General References