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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:51:15 UTC
Update Date2022-03-07 02:56:33 UTC
HMDB IDHMDB0040321
Secondary Accession Numbers
  • HMDB40321
Metabolite Identification
Common Name3',8-Dihydroxy-4',5',7-trimethoxyflavone
Description3',8-Dihydroxy-4',5',7-trimethoxyflavone 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, 3',8-dihydroxy-4',5',7-trimethoxyflavone is considered to be a flavonoid. 3',8-Dihydroxy-4',5',7-trimethoxyflavone has been detected, but not quantified in, fruits. This could make 3',8-dihydroxy-4',5',7-trimethoxyflavone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3',8-Dihydroxy-4',5',7-trimethoxyflavone.
Structure
Data?1547236732
Synonyms
ValueSource
8,3'-Dihydroxy-7,4',5'-trimethoxyflavoneHMDB
Chemical FormulaC18H16O7
Average Molecular Weight344.3154
Monoisotopic Molecular Weight344.089602866
IUPAC Name8-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-7-methoxy-4H-chromen-4-one
Traditional Name8-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-7-methoxychromen-4-one
CAS Registry Number133343-00-7
SMILES
COC1=CC(=CC(O)=C1OC)C1=CC(=O)C2=C(O1)C(O)=C(OC)C=C2
InChI Identifier
InChI=1S/C18H16O7/c1-22-13-5-4-10-11(19)8-14(25-17(10)16(13)21)9-6-12(20)18(24-3)15(7-9)23-2/h4-8,20-21H,1-3H3
InChI KeyRHXKHTYRDAJUEZ-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
  • 7-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 8-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • 1-benzopyran
  • Methoxybenzene
  • Anisole
  • Phenol ether
  • Phenoxy compound
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Point225 - 227 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP2.92ALOGPS
logP1.89ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.32 m³·mol⁻¹ChemAxon
Polarizability34.74 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]+182.35231661259
DarkChem[M-H]-182.63331661259
DeepCCS[M+H]+181.06530932474
DeepCCS[M-H]-178.64530932474
DeepCCS[M-2H]-212.99930932474
DeepCCS[M+Na]+188.45430932474
AllCCS[M+H]+179.732859911
AllCCS[M+H-H2O]+176.332859911
AllCCS[M+NH4]+182.832859911
AllCCS[M+Na]+183.732859911
AllCCS[M-H]-181.332859911
AllCCS[M+Na-2H]-180.832859911
AllCCS[M+HCOO]-180.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3',8-Dihydroxy-4',5',7-trimethoxyflavoneCOC1=CC(=CC(O)=C1OC)C1=CC(=O)C2=C(O1)C(O)=C(OC)C=C25038.5Standard polar33892256
3',8-Dihydroxy-4',5',7-trimethoxyflavoneCOC1=CC(=CC(O)=C1OC)C1=CC(=O)C2=C(O1)C(O)=C(OC)C=C23282.0Standard non polar33892256
3',8-Dihydroxy-4',5',7-trimethoxyflavoneCOC1=CC(=CC(O)=C1OC)C1=CC(=O)C2=C(O1)C(O)=C(OC)C=C23381.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3',8-Dihydroxy-4',5',7-trimethoxyflavone,1TMS,isomer #1COC1=CC(C2=CC(=O)C3=CC=C(OC)C(O)=C3O2)=CC(O[Si](C)(C)C)=C1OC3315.1Semi standard non polar33892256
3',8-Dihydroxy-4',5',7-trimethoxyflavone,1TMS,isomer #2COC1=CC(C2=CC(=O)C3=CC=C(OC)C(O[Si](C)(C)C)=C3O2)=CC(O)=C1OC3278.2Semi standard non polar33892256
3',8-Dihydroxy-4',5',7-trimethoxyflavone,2TMS,isomer #1COC1=CC(C2=CC(=O)C3=CC=C(OC)C(O[Si](C)(C)C)=C3O2)=CC(O[Si](C)(C)C)=C1OC3169.0Semi standard non polar33892256
3',8-Dihydroxy-4',5',7-trimethoxyflavone,1TBDMS,isomer #1COC1=CC(C2=CC(=O)C3=CC=C(OC)C(O)=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1OC3565.6Semi standard non polar33892256
3',8-Dihydroxy-4',5',7-trimethoxyflavone,1TBDMS,isomer #2COC1=CC(C2=CC(=O)C3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3O2)=CC(O)=C1OC3522.2Semi standard non polar33892256
3',8-Dihydroxy-4',5',7-trimethoxyflavone,2TBDMS,isomer #1COC1=CC(C2=CC(=O)C3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1OC3662.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-02di-0319000000-d3f490c750564bdedf452017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1020900000-ff23707959698da106762017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3',8-Dihydroxy-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 - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 10V, Positive-QTOFsplash10-0002-0009000000-e7be1c6e6b64b2ce6cd62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 20V, Positive-QTOFsplash10-0002-1109000000-87855a8c9ffbc1ad49f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 40V, Positive-QTOFsplash10-0kmu-0930000000-47bdfaea4c804b788f612017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 10V, Negative-QTOFsplash10-0006-0009000000-8392498cef82862d9b852017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 20V, Negative-QTOFsplash10-0006-0029000000-c6f6791a6c75f552b2e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 40V, Negative-QTOFsplash10-05ot-0190000000-139aa793261b9b2f22882017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 10V, Negative-QTOFsplash10-0006-0009000000-72fbd0eb75bc9ea05c552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 20V, Negative-QTOFsplash10-0f96-0009000000-eb8d3574738efa76220c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 10V, Positive-QTOFsplash10-0002-0009000000-5dc8eb0c39637af070862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 20V, Positive-QTOFsplash10-0002-0009000000-5dc6fda56294b4fda1a72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',8-Dihydroxy-4',5',7-trimethoxyflavone 40V, Positive-QTOFsplash10-0ugr-0369000000-4f75a64f5f052d5d2c932021-09-22Wishart 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 IDFDB020044
KNApSAcK IDC00004077
Chemspider ID23339933
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257590
PDB IDNot Available
ChEBI IDNot Available
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.. .