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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:33 UTC
Update Date2022-03-07 02:52:35 UTC
HMDB IDHMDB0030547
Secondary Accession Numbers
  • HMDB30547
Metabolite Identification
Common Name3,4',5,7-Tetrahydroxy-6-methoxyflavone
Description3,4',5,7-Tetrahydroxy-6-methoxyflavone 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, 3,4',5,7-tetrahydroxy-6-methoxyflavone is considered to be a flavonoid. 3,4',5,7-Tetrahydroxy-6-methoxyflavone has been detected, but not quantified in, several different foods, such as fruits, german camomiles (Matricaria recutita), safflowers (Carthamus tinctorius), and sweet cherries (Prunus avium). This could make 3,4',5,7-tetrahydroxy-6-methoxyflavone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,4',5,7-Tetrahydroxy-6-methoxyflavone.
Structure
Data?1563862002
Synonyms
ValueSource
6-MethoxykaempferolChEMBL, HMDB
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one, 9ciHMDB
4',5,7-Trihydroxy-6-methoxyflavonolHMDB
3,5,7,4'-Tetrahydroxy-6-methoxyflavoneMeSH, HMDB
Chemical FormulaC16H12O7
Average Molecular Weight316.2623
Monoisotopic Molecular Weight316.058302738
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
Traditional Name6-methoxykaempferol
CAS Registry Number32520-55-1
SMILES
COC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC=C(O)C=C2)C=C1O
InChI Identifier
InChI=1S/C16H12O7/c1-22-16-9(18)6-10-11(13(16)20)12(19)14(21)15(23-10)7-2-4-8(17)5-3-7/h2-6,17-18,20-21H,1H3
InChI KeyOGQSUSFDBWGFFJ-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
  • 6-methoxyflavonoid-skeleton
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Pyranone
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point270 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP1.95ALOGPS
logP2.3ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.95ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.34 m³·mol⁻¹ChemAxon
Polarizability30.56 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]+171.29730932474
DeepCCS[M-H]-168.93930932474
DeepCCS[M-2H]-203.15230932474
DeepCCS[M+Na]+178.37930932474
AllCCS[M+H]+172.032859911
AllCCS[M+H-H2O]+168.432859911
AllCCS[M+NH4]+175.332859911
AllCCS[M+Na]+176.332859911
AllCCS[M-H]-171.032859911
AllCCS[M+Na-2H]-170.332859911
AllCCS[M+HCOO]-169.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4',5,7-Tetrahydroxy-6-methoxyflavoneCOC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC=C(O)C=C2)C=C1O5007.4Standard polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavoneCOC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC=C(O)C=C2)C=C1O3102.7Standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavoneCOC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC=C(O)C=C2)C=C1O3107.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4',5,7-Tetrahydroxy-6-methoxyflavone,1TMS,isomer #1COC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C3200.4Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,1TMS,isomer #2COC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O3198.5Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,1TMS,isomer #3COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O)C(=O)C2=C1O3256.7Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,1TMS,isomer #4COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O3238.1Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C3168.8Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TMS,isomer #2COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C3196.5Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TMS,isomer #3COC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C3084.2Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TMS,isomer #4COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O3113.1Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TMS,isomer #5COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O3205.5Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TMS,isomer #6COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O)C(=O)C2=C1O3250.8Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,3TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C3128.5Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,3TMS,isomer #2COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C3058.6Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,3TMS,isomer #3COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C3092.3Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,3TMS,isomer #4COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O3125.9Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,4TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C3106.8Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,1TBDMS,isomer #1COC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3473.6Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,1TBDMS,isomer #2COC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O3467.1Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,1TBDMS,isomer #3COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O)C(=O)C2=C1O3512.6Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,1TBDMS,isomer #4COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O3496.5Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3714.2Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TBDMS,isomer #2COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3711.0Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TBDMS,isomer #3COC1=C(O)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3618.9Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TBDMS,isomer #4COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O3661.4Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TBDMS,isomer #5COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O3739.2Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,2TBDMS,isomer #6COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O)C(=O)C2=C1O3748.4Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,3TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3910.1Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,3TBDMS,isomer #2COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3765.1Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,3TBDMS,isomer #3COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3837.5Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,3TBDMS,isomer #4COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O3917.9Semi standard non polar33892256
3,4',5,7-Tetrahydroxy-6-methoxyflavone,4TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3965.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0592000000-c5c157abff39602745ed2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone GC-MS (4 TMS) - 70eV, Positivesplash10-03el-1232290000-c24d993a474ec7fa67622017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 10V, Positive-QTOFsplash10-014i-0019000000-ffb6d8b75143085eedf12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 20V, Positive-QTOFsplash10-014i-0059000000-f078617865b395153b482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 40V, Positive-QTOFsplash10-01b9-5960000000-638433e1a89f0ed08f962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 10V, Negative-QTOFsplash10-014i-0109000000-09b61a99a69314a6a85b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 20V, Negative-QTOFsplash10-014i-0269000000-f7617703e6fbdca75da52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 40V, Negative-QTOFsplash10-00yl-5970000000-4dacc69e6b707dd9e90c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 10V, Negative-QTOFsplash10-014i-0009000000-65eaa2011dc9ce7155982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 20V, Negative-QTOFsplash10-014i-0449000000-41a0e07b122e2c20926c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 40V, Negative-QTOFsplash10-030u-2920000000-5ebbfa0238098d05ae672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 10V, Positive-QTOFsplash10-014i-0009000000-d4d9bcf99cd318117dc62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 20V, Positive-QTOFsplash10-014i-0009000000-efc42d2b978a96afd8202021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4',5,7-Tetrahydroxy-6-methoxyflavone 40V, Positive-QTOFsplash10-0159-1912000000-8a0e8cdcbf284ffd73eb2021-09-24Wishart 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 IDFDB002421
KNApSAcK IDC00004593
Chemspider ID4526882
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5377945
PDB IDNot Available
ChEBI ID563477
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .