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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:41:29 UTC
Update Date2022-03-07 02:55:20 UTC
HMDB IDHMDB0037441
Secondary Accession Numbers
  • HMDB37441
Metabolite Identification
Common NameKaempferide
DescriptionKaempferide 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, kaempferide is considered to be a flavonoid. Kaempferide has been detected, but not quantified in, several different foods, such as cloves (Syzygium aromaticum), european plums (Prunus domestica), grapefruits (Citrus X paradisi), herbs and spices, and sour cherries (Prunus cerasus). This could make kaempferide a potential biomarker for the consumption of these foods. Kaempferide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Kaempferide.
Structure
Data?1563863031
Synonyms
ValueSource
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
Chemical FormulaC16H12O6
Average Molecular Weight300.2629
Monoisotopic Molecular Weight300.063388116
IUPAC Name3,5,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Namekaempferide
CAS Registry Number491-54-3
SMILES
COC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=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
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
  • 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point227 - 229 °CNot Available
Boiling Point543.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility327.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.740 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+171.75130932474
DeepCCS[M-H]-169.39330932474
DeepCCS[M-2H]-202.82630932474
DeepCCS[M+Na]+178.05330932474
AllCCS[M+H]+168.632859911
AllCCS[M+H-H2O]+164.932859911
AllCCS[M+NH4]+172.032859911
AllCCS[M+Na]+173.032859911
AllCCS[M-H]-168.832859911
AllCCS[M+Na-2H]-168.132859911
AllCCS[M+HCOO]-167.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
KaempferideCOC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O14627.7Standard polar33892256
KaempferideCOC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O13033.5Standard non polar33892256
KaempferideCOC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O13066.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Kaempferide,1TMS,isomer #1COC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C=C13103.2Semi standard non polar33892256
Kaempferide,1TMS,isomer #2COC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C13144.0Semi standard non polar33892256
Kaempferide,1TMS,isomer #3COC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C13193.9Semi standard non polar33892256
Kaempferide,2TMS,isomer #1COC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C13052.7Semi standard non polar33892256
Kaempferide,2TMS,isomer #2COC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C13023.7Semi standard non polar33892256
Kaempferide,2TMS,isomer #3COC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C13140.3Semi standard non polar33892256
Kaempferide,3TMS,isomer #1COC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C13045.4Semi standard non polar33892256
Kaempferide,1TBDMS,isomer #1COC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C=C13401.5Semi standard non polar33892256
Kaempferide,1TBDMS,isomer #2COC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C13409.5Semi standard non polar33892256
Kaempferide,1TBDMS,isomer #3COC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C13458.8Semi standard non polar33892256
Kaempferide,2TBDMS,isomer #1COC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C13574.9Semi standard non polar33892256
Kaempferide,2TBDMS,isomer #2COC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C13545.5Semi standard non polar33892256
Kaempferide,2TBDMS,isomer #3COC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C13642.3Semi standard non polar33892256
Kaempferide,3TBDMS,isomer #1COC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C13767.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0791000000-3624bd10f2d622665fc62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferide GC-MS (3 TMS) - 70eV, Positivesplash10-0fkc-2271950000-26095b3d4aa33777ac682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Kaempferide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 20V, Negative-QTOFsplash10-014i-0940000000-563e589b151a0bfb9b742017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 40V, Negative-QTOFsplash10-0lz9-0960000000-0dce6ae0f50391aaacb92017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 30V, Negative-QTOFsplash10-001i-0190000000-172ba30afca1dd6391fe2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 10V, Negative-QTOFsplash10-001i-0190000000-172ba30afca1dd6391fe2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 50V, Negative-QTOFsplash10-001i-0190000000-172ba30afca1dd6391fe2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 20V, Negative-QTOFsplash10-001j-0090000000-847e2fc8fc2afde2e8a42017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 40V, Negative-QTOFsplash10-0lz9-0960000000-0dce6ae0f50391aaacb92017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 30V, Negative-QTOFsplash10-001i-0190000000-172ba30afca1dd6391fe2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 10V, Negative-QTOFsplash10-0002-0091000000-57350f569441ea5d880f2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 50V, Negative-QTOFsplash10-03fr-0960000000-979796d59b40dcf379392017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide ESI-TOF 10V, Negative-QTOFsplash10-0002-0092000000-04e7a3c959e15791ba362017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOFsplash10-000t-0290000000-fa97943058aecfae64242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOFsplash10-0lz9-1930000000-02a76c9065a4d7efea342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOFsplash10-000t-1390000000-6bcab21096c8f7188eac2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOFsplash10-0002-0090000000-e9170e82b1995679aeb32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOFsplash10-001j-0190000000-a2ea43e49a14ecee430e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOFsplash10-0pc0-0930000000-7f0eb2e35a23d80bbe812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide LC-ESI-TOF , negative-QTOFsplash10-001j-0090000000-847e2fc8fc2afde2e8a42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Kaempferide LC-ESI-TOF , negative-QTOFsplash10-0lz9-0960000000-0dce6ae0f50391aaacb92017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferide 10V, Positive-QTOFsplash10-0udi-0009000000-074f2d87992a7d211bc52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferide 20V, Positive-QTOFsplash10-0udi-0019000000-b776fbc53676f3fbdefc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferide 40V, Positive-QTOFsplash10-0udr-6890000000-8ec28b3eec5b952d08202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferide 10V, Negative-QTOFsplash10-0002-0090000000-47a5eafa7deb386a7c0a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferide 20V, Negative-QTOFsplash10-0002-0090000000-2ea66ca52cf34d1668872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Kaempferide 40V, Negative-QTOFsplash10-0f89-3690000000-d8131b75040f06793f222016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016499
KNApSAcK IDC00001060
Chemspider ID4444985
KEGG Compound IDC10098
BioCyc IDCPD-7252
BiGG IDNot Available
Wikipedia LinkKaempferide
METLIN IDNot Available
PubChem Compound5281666
PDB IDNot Available
ChEBI ID6099
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1504521
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

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
Reactions
Kaempferide → 6-{[3,5-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Kaempferide → 6-{[3,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Kaempferide → 6-{[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails