Showing metabocard for Kaempferol (BMDB0005801)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:18:44 UTC
Update Date2020-04-22 15:16:23 UTC
BMDB IDBMDB0005801
Secondary Accession Numbers
  • BMDB05801
Metabolite 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. Kaempferol exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Kaempferol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,4',5,7-TetrahydroxyflavoneChEBI
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-5,7,4'-trihydroxyflavonolChEBI
5,7,4'-TrihydroxyflavonolChEBI
C.I. 75640ChEBI
CampherolChEBI
Indigo yellowChEBI
KaempherolChEBI
KampherolChEBI
KempferolChEBI
NimbecetinChEBI
PelargidenolonChEBI
PopulnetinChEBI
RhamnoluteinChEBI
RhamnolutinChEBI
RobigeninChEBI
SwartziolChEBI
TrifolitinChEBI
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneKegg
3,4',5,7-Tetrahydroxy-flavone (7ci,8ci)HMDB
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-oneHMDB
KampferolHMDB
3,4’,5,7-TetrahydroxyflavonePhytoBank
3,5,7,4'-TetrahydroxyflavonePhytoBank
3,5,7,4’-TetrahydroxyflavonePhytoBank
3'-DeoxyquercetinPhytoBank
3’-DeoxyquercetinPhytoBank
5,7,4’-TrihydroxyflavonolPhytoBank
KaemferolPhytoBank
KaempferolPhytoBank
KampcetinPhytoBank
PelargidenonPhytoBank
Chemical FormulaC15H10O6
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
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
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
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0079-1963700000-1d3775db7c536f63b70cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0bt9-0000290000-4a7068686e907a319864View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4290000000-ccb984ce16e32c25d878View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0079-1963700000-1d3775db7c536f63b70cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-0000290000-4a7068686e907a319864View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-0590000000-3bfd778520b9c39bc4baView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0mc0-2150190000-3a2826fb2ce8460675bcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-f0101bac1cb6491794f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-0690000000-3afcadc746823bc03ebdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0v4i-5900000000-6a870572cf8a486dd6b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-06-H) , Positivesplash10-000i-4290000000-75bfe61cc0a42797e86aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-000i-0090000000-ead9f201b8c5b6b6e46eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0190000000-2bc892de84e0225a49cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052u-1930000000-08779ff26cd586d78e41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udr-0920000000-97d144af795812440c46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0290000000-5573e7fd91cf25805a11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014s-2920000000-397e01f2d2cf07025409View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-1920000000-891ca58b63b857f31594View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0079-0090040000-5111d04af3f3d3e053c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0950000000-580cab3c0e471a3f4e00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0950000000-580cab3c0e471a3f4e00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-066r-0930000000-f40d69c592d60004cae0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-066r-0930000000-f40d69c592d60004cae0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0950000000-580cab3c0e471a3f4e00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0091000000-295f056c177e6e49fb6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-066r-0930000000-f40d69c592d60004cae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-0d8eaf63d3860cdc1cbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-3969010f013a967001daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-6790000000-5668e7d87a859b519804View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-4cba2efdae1d7d094e17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-489c309b159fce3df0d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4950000000-9d8aab7149b59126c14aView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005801
DrugBank IDDB01852
Phenol Explorer Compound ID290
FooDB 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
Synthesis ReferenceWuth, B. Indigo Yellow. Faerber-Zeitung (1912), 22 343-5. CODEN: FAZTAZ CAN 6:966 AN 1912:966
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Dehydrogenase/reductase SDR family member 4
General function:
Lipid transport and metabolism
Specific function:
Reduces all-trans-retinal and 9-cis retinal. Can also catalyze the oxidation of all-trans-retinol with NADP as co-factor, but with much lower efficiency. Reduces alkyl phenyl ketones and alpha-dicarbonyl compounds with aromatic rings, such as pyrimidine-4-aldehyde, 3-benzoylpyridine, 4-benzoylpyridine, menadione and 4-hexanoylpyridine. Has no activity towards aliphatic aldehydes and ketones (By similarity).
Gene Name:
DHRS4
Uniprot ID:
Q8SPU8
Molecular weight:
29440.0