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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:10 UTC
Update Date2022-03-07 02:52:27 UTC
HMDB IDHMDB0030161
Secondary Accession Numbers
  • HMDB30161
Metabolite Identification
Common Name5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone
Description5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone, also known as 5-OH-HXMF, belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, 5-hydroxy-3,3',4',6,7,8-hexamethoxyflavone is considered to be a flavonoid. 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone has been detected, but not quantified in, citrus and sweet oranges (Citrus sinensis). This could make 5-hydroxy-3,3',4',6,7,8-hexamethoxyflavone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone.
Structure
Data?1563861946
Synonyms
ValueSource
2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,6,7,8-tetramethoxy-4H-chromen-4-oneMeSH
5-OH-HXMFMeSH
2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,6,7,8-tetramethoxy-4H-1-benzopyran-4-oneHMDB
5-Hydroxy-3,6,7,8,3',4'-hexamethoxyflavoneHMDB
5-Hydroxy-3,6,7,8,3'4'-hexamethoxyflavoneHMDB
Chemical FormulaC21H22O9
Average Molecular Weight418.394
Monoisotopic Molecular Weight418.126382302
IUPAC Name2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7,8-tetramethoxy-4H-chromen-4-one
Traditional Name2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7,8-tetramethoxychromen-4-one
CAS Registry Number1176-88-1
SMILES
COC1=C(OC)C=C(C=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1
InChI Identifier
InChI=1S/C21H22O9/c1-24-11-8-7-10(9-12(11)25-2)16-18(26-3)14(22)13-15(23)19(27-4)21(29-6)20(28-5)17(13)30-16/h7-9,23H,1-6H3
InChI KeyJDVPHCLYMGBZLE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • 3-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • 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 Point110 - 111 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility46.49 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP2.71ALOGPS
logP2.39ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area101.91 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.99 m³·mol⁻¹ChemAxon
Polarizability42.43 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.0931661259
DarkChem[M-H]-196.83631661259
DeepCCS[M+H]+192.81930932474
DeepCCS[M-H]-190.46130932474
DeepCCS[M-2H]-224.01230932474
DeepCCS[M+Na]+199.22630932474
AllCCS[M+H]+197.332859911
AllCCS[M+H-H2O]+194.632859911
AllCCS[M+NH4]+199.832859911
AllCCS[M+Na]+200.632859911
AllCCS[M-H]-202.032859911
AllCCS[M+Na-2H]-202.232859911
AllCCS[M+HCOO]-202.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavoneCOC1=C(OC)C=C(C=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O15210.9Standard polar33892256
5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavoneCOC1=C(OC)C=C(C=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O13479.0Standard non polar33892256
5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavoneCOC1=C(OC)C=C(C=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O13360.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone,1TMS,isomer #1COC1=CC=C(C2=C(OC)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(OC)C(OC)=C3O2)C=C1OC3271.4Semi standard non polar33892256
5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone,1TBDMS,isomer #1COC1=CC=C(C2=C(OC)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(OC)C(OC)=C3O2)C=C1OC3477.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0029400000-57354dd4008627e292e22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-1010900000-c4521f6a592768feac4d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone , positive-QTOFsplash10-000i-0239000000-6849086f514ea7de3a5c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 10V, Positive-QTOFsplash10-014i-0000900000-6ae9bde9e4fb3b701c5e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 20V, Positive-QTOFsplash10-014i-0001900000-eff64a1e051c3f89b95b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 40V, Positive-QTOFsplash10-00di-0139000000-2dd1f0f0bd72020e53202016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 10V, Negative-QTOFsplash10-014i-0000900000-d8d9465ff748443296e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 20V, Negative-QTOFsplash10-014i-0006900000-6b422da150e8f8e50c202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 40V, Negative-QTOFsplash10-0fmj-1359000000-92bb949e91fb98996e8e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 10V, Positive-QTOFsplash10-014i-0000900000-a12148ee24803ea188362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 20V, Positive-QTOFsplash10-014i-0000900000-a43e9f6cc44fced3353e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 40V, Positive-QTOFsplash10-00or-1091300000-d785c146834056a8b4022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 10V, Negative-QTOFsplash10-014i-0000900000-0a6930dd8545a0febcdf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 20V, Negative-QTOFsplash10-014i-0031900000-cc8cafc7600cfaa2c7132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone 40V, Negative-QTOFsplash10-07ku-2893100000-e07230b20ad4374b2e6b2021-09-22Wishart 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 IDFDB001970
KNApSAcK IDC00004802
Chemspider ID120189
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound136417
PDB IDNot Available
ChEBI ID221147
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1817521
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.. .