Record Information
Version1.0
Creation date2010-04-08 22:12:28 UTC
Update date2018-05-29 01:26:46 UTC
Primary IDFDB016499
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKaempferide
DescriptionIsolated from roots of Alpinia officinarum (lesser galangal). Kaempferide is found in many foods, some of which are herbs and spices, cloves, sour cherry, and european plum.
CAS Number491-54-3
Structure
Thumb
Synonyms
SynonymSource
1.3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4-benzopyroneChEBI
4'-O-MethylkaempferolChEBI
CampherideChEBI
Kaempferol 4'-methyl etherChEBI
KempferideKegg
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4-benzopyroneHMDB
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9ciHMDB
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-oneHMDB
3,5,7-Trihydroxy-4'-methoxy-flavoneHMDB
4'-Methoxy-3,5,7-trihydroxy-flavanoneHMDB
4'-Methoxy-3,5,7-trihydroxyflavoneHMDB
4'-MethylkaempferolHMDB
5,7-Dihydroxy-4'-methoxyflavonolHMDB
KaemferideHMDB
KaempferidHMDB
KampferideHMDB
KampherideHMDB
3 5 7-Trihydroxy-4'-methoxyflavoneMeSH
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
3,5,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-onebiospider
Flavanone, 4'-methoxy-3,5,7-trihydroxy-biospider
Flavone, 3,5,7-trihydroxy-4'-methoxy-biospider
Kaempferidedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.075 g/LALOGPS
logP2.48ALOGPS
logP2.61ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.44ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.36 m³·mol⁻¹ChemAxon
Polarizability29.73 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H12O6
IUPAC name3,5,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C16H12O6/c1-21-10-4-2-8(3-5-10)16-15(20)14(19)13-11(18)6-9(17)7-12(13)22-16/h2-7,17-18,20H,1H3
InChI KeySQFSKOYWJBQGKQ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight300.2629
Monoisotopic Molecular Weight300.063388116
Classification
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
  • 4p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.00%; H 4.03%; O 31.97%DFC
Melting PointMp 227-229°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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0791000000-3624bd10f2d622665fc6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fkc-2271950000-26095b3d4aa33777ac68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0940000000-563e589b151a0bfb9b74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0lz9-0960000000-0dce6ae0f50391aaacb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0190000000-172ba30afca1dd6391feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0190000000-172ba30afca1dd6391feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-001i-0190000000-172ba30afca1dd6391feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001j-0090000000-847e2fc8fc2afde2e8a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0lz9-0960000000-0dce6ae0f50391aaacb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0190000000-172ba30afca1dd6391feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0091000000-57350f569441ea5d880fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-03fr-0960000000-979796d59b40dcf37939View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0092000000-04e7a3c959e15791ba36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000t-0290000000-fa97943058aecfae6424View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0lz9-1930000000-02a76c9065a4d7efea34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000t-1390000000-6bcab21096c8f7188eacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0090000000-e9170e82b1995679aeb3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001j-0190000000-a2ea43e49a14ecee430eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0pc0-0930000000-7f0eb2e35a23d80bbe81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001j-0090000000-847e2fc8fc2afde2e8a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0lz9-0960000000-0dce6ae0f50391aaacb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-074f2d87992a7d211bc5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0019000000-b776fbc53676f3fbdefcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-6890000000-8ec28b3eec5b952d0820View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-47a5eafa7deb386a7c0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-2ea66ca52cf34d166887View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f89-3690000000-d8131b75040f06793f22View in MoNA
ChemSpider ID4444985
ChEMBL IDCHEMBL40919
KEGG Compound IDC10098
Pubchem Compound ID5281666
Pubchem Substance IDNot Available
ChEBI ID6099
Phenol-Explorer ID311
DrugBank IDNot Available
HMDB IDHMDB37441
CRC / DFC (Dictionary of Food Compounds) IDKRJ00-L:KRJ00-L
EAFUS IDNot Available
Dr. Duke IDKAEMPFERIDE
BIGG IDNot Available
KNApSAcK IDC00001060
HET 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
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti mutagenicDUKE
aromatase inhibitor50790 An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.DUKE
quinone-reductase inducerDUKE
topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.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.