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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:21 UTC
Update Date2022-03-07 02:52:43 UTC
HMDB IDHMDB0030842
Secondary Accession Numbers
  • HMDB30842
Metabolite Identification
Common Name4',5,7-Trimethoxyflavone
Description4',5,7-Trimethoxyflavone, also known as trimethylapigenin, belongs to the class of organic compounds known as 7-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 4',5,7-trimethoxyflavone is considered to be a flavonoid lipid molecule. 4',5,7-Trimethoxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4',5,7-trimethoxyflavone has been detected, but not quantified in, a few different foods, such as citrus, mandarin orange (clementine, tangerine), and sweet oranges. This could make 4',5,7-trimethoxyflavone a potential biomarker for the consumption of these foods.
Structure
Data?1586284318
Synonyms
ValueSource
4',5,7-Trimethyl-apigeninMeSH
5,7,4'-TrimethylapigeninMeSH
4'57-TrimethoxyflavoneChEMBL, HMDB
4',5,7-Trimethoxy-flavoneHMDB
5,7,4'-TrimethoxyflavoneHMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-1-benzenopyran-4-oneHMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-oneHMDB
6-Hydroxy-4',5,7-trimethoxyflavoneHMDB
Apigenin 5,7,4'-trimethyl etherHMDB
Apigenin trimethyl etherHMDB
4',5,7-TrimethoxyflavoneMeSH
4’,5,7-TrimethoxyflavoneHMDB
5,7,4'-Tri-O-methylapigeninHMDB
5,7,4'-TrimethoxyapigeninHMDB
5,7,4’-Tri-O-methylapigeninHMDB
5,7,4’-TrimethoxyapigeninHMDB
5,7,4’-TrimethoxyflavoneHMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-oneHMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)chromoneHMDB
5,7-Dimethoxy-4-oxo-2-(4-methoxyphenyl)-4H-1-benzopyranHMDB
Tri-O-methylapigeninHMDB
TrimethylapigeninHMDB
Chemical FormulaC18H16O5
Average Molecular Weight312.3166
Monoisotopic Molecular Weight312.099773622
IUPAC Name5,7-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Name5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
CAS Registry Number5631-70-9
SMILES
COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O1
InChI Identifier
InChI=1S/C18H16O5/c1-20-12-6-4-11(5-7-12)15-10-14(19)18-16(22-3)8-13(21-2)9-17(18)23-15/h4-10H,1-3H3
InChI KeyZXJJBDHPUHUUHD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • 5-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • Flavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous ester
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Point156 - 157 °CNot Available
Boiling Point506.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility6.51 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.530 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.21ALOGPS
logP2.49ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)15.54ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity86.36 m³·mol⁻¹ChemAxon
Polarizability33.03 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
DarkChem[M+H]+175.2731661259
DarkChem[M-H]-177.12631661259
DeepCCS[M+H]+173.28830932474
DeepCCS[M-H]-170.9330932474
DeepCCS[M-2H]-204.09330932474
DeepCCS[M+Na]+179.38130932474
AllCCS[M+H]+172.832859911
AllCCS[M+H-H2O]+169.232859911
AllCCS[M+NH4]+176.232859911
AllCCS[M+Na]+177.132859911
AllCCS[M-H]-176.032859911
AllCCS[M+Na-2H]-175.432859911
AllCCS[M+HCOO]-174.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4',5,7-TrimethoxyflavoneCOC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O14298.7Standard polar33892256
4',5,7-TrimethoxyflavoneCOC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O12895.2Standard non polar33892256
4',5,7-TrimethoxyflavoneCOC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O13134.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4',5,7-Trimethoxyflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qa-0691000000-7a823829ea08d5c449872017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4',5,7-Trimethoxyflavone 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 - 4',5,7-Trimethoxyflavone 10V, Positive-QTOFsplash10-03di-0009000000-5c2fa314b535098da3c32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 20V, Positive-QTOFsplash10-03di-0009000000-e66ded4021486610bfbe2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 40V, Positive-QTOFsplash10-053r-1490000000-a1ba798957d115c766da2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 10V, Negative-QTOFsplash10-03di-0009000000-6fd59ab6ee43b4030a5c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 20V, Negative-QTOFsplash10-03di-0029000000-1598e4635c488fb5e5242015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 40V, Negative-QTOFsplash10-0kcr-1390000000-6872b99524899c8fbf572015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 10V, Positive-QTOFsplash10-03di-0009000000-0c9c5e8761c67e87c6242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 20V, Positive-QTOFsplash10-03di-0019000000-d5759b18375da517980a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 40V, Positive-QTOFsplash10-0g4j-0190000000-5d008847ec007268d4ec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 10V, Negative-QTOFsplash10-03di-0009000000-70f2c2cfe291372814552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 20V, Negative-QTOFsplash10-03xs-0097000000-951d276ce9092ed6732e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB002800
KNApSAcK IDC00003821
Chemspider ID72029
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound79730
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1701731
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.. .