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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:55 UTC
Update Date2022-03-07 02:52:11 UTC
HMDB IDHMDB0029522
Secondary Accession Numbers
  • HMDB29522
Metabolite Identification
Common Name5,7-Dihydroxy-3-methoxyflavone
Description5,7-Dihydroxy-3-methoxyflavone, also known as galangin 3-methyl ether or 3-methylgalangin, belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, 5,7-dihydroxy-3-methoxyflavone is considered to be a flavonoid. 5,7-Dihydroxy-3-methoxyflavone is found, on average, in the highest concentration within mexican oreganos (Lippia graveolens). 5,7-Dihydroxy-3-methoxyflavone has also been detected, but not quantified in, herbs and spices. This could make 5,7-dihydroxy-3-methoxyflavone a potential biomarker for the consumption of these foods. 5,7-Dihydroxy-3-methoxyflavone 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 5,7-Dihydroxy-3-methoxyflavone.
Structure
Data?1582753430
Synonyms
ValueSource
Galangin 3-methyl etherChEBI
5,7-Dihydroxy-3-methoxy-2-phenyl-4H-1-benzopyran-4-oneKegg
3-MethylgalanginMeSH
5,7-Dihydroxy-3-methoxy-2-phenyl-4H-chromen-4-oneHMDB
5,7-Dihydroxy-3-methoxyflavoneChEBI
Chemical FormulaC16H12O5
Average Molecular Weight284.2635
Monoisotopic Molecular Weight284.068473494
IUPAC Name5,7-dihydroxy-3-methoxy-2-phenyl-4H-chromen-4-one
Traditional Namegalangin 3-methyl ether
CAS Registry Number6665-74-3
SMILES
COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H12O5/c1-20-16-14(19)13-11(18)7-10(17)8-12(13)21-15(16)9-5-3-2-4-6-9/h2-8,17-18H,1H3
InChI KeyLYISDADPVOHJBJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent3-O-methylated flavonoids
Alternative Parents
Substituents
  • 3-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • 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
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point299 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility336.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP3.49ALOGPS
logP2.88ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.44ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.65 m³·mol⁻¹ChemAxon
Polarizability28.44 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]+164.54730932474
DeepCCS[M-H]-162.18930932474
DeepCCS[M-2H]-195.13830932474
DeepCCS[M+Na]+170.6430932474
AllCCS[M+H]+164.032859911
AllCCS[M+H-H2O]+160.132859911
AllCCS[M+NH4]+167.632859911
AllCCS[M+Na]+168.632859911
AllCCS[M-H]-164.832859911
AllCCS[M+Na-2H]-164.032859911
AllCCS[M+HCOO]-163.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,7-Dihydroxy-3-methoxyflavoneCOC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C14081.9Standard polar33892256
5,7-Dihydroxy-3-methoxyflavoneCOC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C12635.7Standard non polar33892256
5,7-Dihydroxy-3-methoxyflavoneCOC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=CC=C12739.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,7-Dihydroxy-3-methoxyflavone,1TMS,isomer #1COC1=C(C2=CC=CC=C2)OC2=CC(O[Si](C)(C)C)=CC(O)=C2C1=O2736.4Semi standard non polar33892256
5,7-Dihydroxy-3-methoxyflavone,1TMS,isomer #2COC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O2697.3Semi standard non polar33892256
5,7-Dihydroxy-3-methoxyflavone,2TMS,isomer #1COC1=C(C2=CC=CC=C2)OC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C1=O2738.4Semi standard non polar33892256
5,7-Dihydroxy-3-methoxyflavone,1TBDMS,isomer #1COC1=C(C2=CC=CC=C2)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C1=O2983.3Semi standard non polar33892256
5,7-Dihydroxy-3-methoxyflavone,1TBDMS,isomer #2COC1=C(C2=CC=CC=C2)OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O2945.9Semi standard non polar33892256
5,7-Dihydroxy-3-methoxyflavone,2TBDMS,isomer #1COC1=C(C2=CC=CC=C2)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3175.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-0980000000-40965d7fa7571c58982c2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone GC-MS (2 TMS) - 70eV, Positivesplash10-044i-3479600000-ac2b27802da118b5e4602017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxy-3-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 - 5,7-Dihydroxy-3-methoxyflavone 10V, Positive-QTOFsplash10-000i-0090000000-d1d6d620c716e8d78e492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 20V, Positive-QTOFsplash10-000i-0090000000-1abf15fd1c5dd8e8129b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 40V, Positive-QTOFsplash10-0uxr-5790000000-3393b162a05d00da6e182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 10V, Negative-QTOFsplash10-001i-0090000000-875cfdc42c4400b1eafa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 20V, Negative-QTOFsplash10-001i-0090000000-70c109aa6f75af9a86922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 40V, Negative-QTOFsplash10-0fsi-1950000000-b51e0725d704b4e9bce42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 10V, Negative-QTOFsplash10-001i-0090000000-1c01ef5aa5f04eb0a5462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 20V, Negative-QTOFsplash10-001i-0390000000-03e34ed2cb8f2fc7eb602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 40V, Negative-QTOFsplash10-0fv0-3910000000-48ca0d2a9ce649295c0c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 10V, Positive-QTOFsplash10-000i-0090000000-51f99bf4d16155b2c7b02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 20V, Positive-QTOFsplash10-000i-0090000000-e6b110f8170ddb7f89fd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-methoxyflavone 40V, Positive-QTOFsplash10-0udr-1920000000-cbbb3db52b12c19671682021-09-24Wishart 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 ID386
FooDB IDFDB000658
KNApSAcK IDC00004534
Chemspider ID4445223
KEGG Compound IDC11577
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281946
PDB IDNot Available
ChEBI ID1602
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1810171
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.. .