Showing Compound Card for Kaempferol (CDB000373)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 26 proteinsXML
Show more...Show more...Show more...
Record Information
Version1.0
Created at2020-03-19 00:33:39 UTC
Updated at2022-12-13 19:31:28 UTC
CannabisDB IDCDB000373
Secondary Accession NumbersNot Available
Cannabis Compound 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 a flavonoid lipid molecule. Kaempferol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Kaempferol is a bitter tasting compound. It is very widespread in the plant world and is found in Brassicaceae, Apocynaceae, Dilleniaceae, Ranunculaceae and Leguminosae. It is detected in apples, tomatoes, green tea, potatoes, onions, brussels sprouts, squash, cucumbers, lettuce, green beans, peaches, blackberries, raspberries, spinach, grapes, broccoli, capers, chives, kale, garden cress, fennel, lovage, dill weed and tarragon (PMID: 21428901 ). Kaempferol is also one of several flavonoids that are found in cannabis plants (PMID: 6991645 ). Kaempferol is a biomarker for the consumption of dried and cooked beans. Many glycosides of kaempferol, such as kaempferitrin and astragalin, have been isolated as natural products from plants. Kaempferol consumption in tea and broccoli has been associated with reduced risk of heart disease. Kaempferol has numerous protective properties and has been used to treat intervertebral disc degeneration and colitis, post-menopausal bone loss, acute lung injury and has beneficial effects against cancer, liver injury, obesity and diabetes, and inhibits vascular endothelial inflammation. These treatments and protective properties of kaempferol and the potential mechanisms that kaempferol exerts these effects are part of this review ( PMID: 31572524 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC15H10O6
Average Molecular Weight286.24
Monoisotopic Molecular Weight286.0477
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(O)C=C(O)C=C2O1
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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point285 - 287 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSKaempferol, non-derivatized, GC-MS Spectrumsplash10-0079-1963700000-1d3775db7c536f63b70cSpectrum
GC-MSKaempferol, 5 TMS, GC-MS Spectrumsplash10-0bt9-0000290000-4a7068686e907a319864Spectrum
GC-MSKaempferol, non-derivatized, GC-MS Spectrumsplash10-000i-4290000000-ccb984ce16e32c25d878Spectrum
GC-MSKaempferol, non-derivatized, GC-MS Spectrumsplash10-0079-1963700000-1d3775db7c536f63b70cSpectrum
GC-MSKaempferol, non-derivatized, GC-MS Spectrumsplash10-0bt9-0000290000-4a7068686e907a319864Spectrum
Predicted GC-MSKaempferol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052r-0590000000-3bfd778520b9c39bc4baSpectrum
Predicted GC-MSKaempferol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0mc0-2150190000-3a2826fb2ce8460675bcSpectrum
Predicted GC-MSKaempferol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.014 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00443 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.00364 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.00446 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.00459 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.00735 mg/g dry wt
    • David S. Wishart,...
 details
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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Calderon-Montano JM, Burgos-Moron E, Perez-Guerrero C, Lopez-Lazaro M: A review on the dietary flavonoid kaempferol. Mini Rev Med Chem. 2011 Apr;11(4):298-344. doi: 10.2174/138955711795305335. [PubMed:21428901 ]
  3. Ren J, Lu Y, Qian Y, Chen B, Wu T, Ji G: Recent progress regarding kaempferol for the treatment of various diseases. Exp Ther Med. 2019 Oct;18(4):2759-2776. doi: 10.3892/etm.2019.7886. Epub 2019 Aug 13. [PubMed:31572524 ]

Only showing the first 10 proteins. There are 26 proteins in total.

Show All

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91

Only showing the first 10 proteins. There are 26 proteins in total.

Show All