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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:52 UTC
Update Date2022-03-07 02:52:11 UTC
HMDB IDHMDB0029512
Secondary Accession Numbers
  • HMDB29512
Metabolite Identification
Common Name4',5-Dihydroxy-7-methoxy-6-methylflavone
Description4',5-Dihydroxy-7-methoxy-6-methylflavone, also known as 8-demethylsideroxylin, 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-dihydroxy-7-methoxy-6-methylflavone is considered to be a flavonoid. 4',5-Dihydroxy-7-methoxy-6-methylflavone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 4',5-Dihydroxy-7-methoxy-6-methylflavone.
Structure
Data?1582753429
Synonyms
ValueSource
5,4'-Dihydroxy-7-methoxy-6-methylflavoneChEBI
5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-4H-1-benzopyran-4-oneHMDB
8-DemethylsideroxylinHMDB
8-Desmethyl-sideroxylinHMDB
8-DesmethylsideroxylinHMDB
Chemical FormulaC17H14O5
Average Molecular Weight298.2901
Monoisotopic Molecular Weight298.084123558
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-4H-chromen-4-one
Traditional Name8-demethylsideroxylin
CAS Registry Number80621-54-1
SMILES
COC1=C(C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C17H14O5/c1-9-13(21-2)8-15-16(17(9)20)12(19)7-14(22-15)10-3-5-11(18)6-4-10/h3-8,18,20H,1-2H3
InChI KeyVQCXCCMCKDSXMQ-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
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen 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 Point284 - 286 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP3.51ALOGPS
logP3.37ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)8.52ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity82.44 m³·mol⁻¹ChemAxon
Polarizability30.98 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]+172.2131661259
DarkChem[M-H]-174.50231661259
DeepCCS[M+H]+174.3430932474
DeepCCS[M-H]-171.98230932474
DeepCCS[M-2H]-206.04830932474
DeepCCS[M+Na]+181.37530932474
AllCCS[M+H]+168.332859911
AllCCS[M+H-H2O]+164.632859911
AllCCS[M+NH4]+171.732859911
AllCCS[M+Na]+172.732859911
AllCCS[M-H]-169.632859911
AllCCS[M+Na-2H]-168.832859911
AllCCS[M+HCOO]-168.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4',5-Dihydroxy-7-methoxy-6-methylflavoneCOC1=C(C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C14295.2Standard polar33892256
4',5-Dihydroxy-7-methoxy-6-methylflavoneCOC1=C(C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C13045.9Standard non polar33892256
4',5-Dihydroxy-7-methoxy-6-methylflavoneCOC1=C(C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C13169.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4',5-Dihydroxy-7-methoxy-6-methylflavone,1TMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C)=C1C)C(=O)C=C(C1=CC=C(O)C=C1)O23111.0Semi standard non polar33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone,1TMS,isomer #2COC1=CC2=C(C(O)=C1C)C(=O)C=C(C1=CC=C(O[Si](C)(C)C)C=C1)O23205.7Semi standard non polar33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone,2TMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C)=C1C)C(=O)C=C(C1=CC=C(O[Si](C)(C)C)C=C1)O23194.8Semi standard non polar33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone,1TBDMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1C)C(=O)C=C(C1=CC=C(O)C=C1)O23363.5Semi standard non polar33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone,1TBDMS,isomer #2COC1=CC2=C(C(O)=C1C)C(=O)C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O23442.8Semi standard non polar33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone,2TBDMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1C)C(=O)C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O23689.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0390000000-96ed347dca125a37ab8b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone GC-MS (2 TMS) - 70eV, Positivesplash10-00vi-3359700000-39a3db4ae015d2759a4c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 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-Dihydroxy-7-methoxy-6-methylflavone 10V, Positive-QTOFsplash10-0002-0090000000-e1cc5ed174d56766f3402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 20V, Positive-QTOFsplash10-0002-0090000000-5de2f7f2587cc093e3622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 40V, Positive-QTOFsplash10-0fb9-3790000000-315fa43c144dda47386d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 10V, Negative-QTOFsplash10-0002-0090000000-cba666d2db9505376ec12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 20V, Negative-QTOFsplash10-0002-0090000000-08b338d59b21f8b653062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 40V, Negative-QTOFsplash10-0170-4960000000-ce232a098b2d2f42f3112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 10V, Positive-QTOFsplash10-0002-0090000000-9b410a4cce68ead03b3b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 20V, Positive-QTOFsplash10-0002-0090000000-68753556a141556a2a952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 40V, Positive-QTOFsplash10-0a4i-0290000000-c8e4a7bfee4317a1cf502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 10V, Negative-QTOFsplash10-0002-0090000000-bfe4eca51ec0a2a32edf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 20V, Negative-QTOFsplash10-0f7k-0090000000-11f4cbb2469ab3dc43762021-09-25Wishart 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 IDFDB000647
KNApSAcK IDC00013597
Chemspider ID24843977
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44258359
PDB IDNot Available
ChEBI ID69917
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.. .