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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:56 UTC
Update Date2022-03-07 02:52:37 UTC
HMDB IDHMDB0030611
Secondary Accession Numbers
  • HMDB30611
Metabolite Identification
Common Name5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone
Description5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone, also known as gossypetin 3,7,3',4'-tetramethyl ether, 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, 5,8-dihydroxy-3,3',4',7-tetramethoxyflavone is considered to be a flavonoid. Based on a literature review very few articles have been published on 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone.
Structure
Data?1563862012
Synonyms
ValueSource
Gossypetin 3,7,3',4'-tetramethyl etherHMDB
Gossypetin-3,3',4',7-tetramethyletherHMDB
Chemical FormulaC19H18O8
Average Molecular Weight374.3414
Monoisotopic Molecular Weight374.100167552
IUPAC Name2-(3,4-dimethoxyphenyl)-5,8-dihydroxy-3,7-dimethoxy-4H-chromen-4-one
Traditional Name2-(3,4-dimethoxyphenyl)-5,8-dihydroxy-3,7-dimethoxychromen-4-one
CAS Registry Number7380-44-1
SMILES
COC1=C(O)C2=C(C(O)=C1)C(=O)C(OC)=C(O2)C1=CC(OC)=C(OC)C=C1
InChI Identifier
InChI=1S/C19H18O8/c1-23-11-6-5-9(7-12(11)24-2)17-19(26-4)16(22)14-10(20)8-13(25-3)15(21)18(14)27-17/h5-8,20-21H,1-4H3
InChI KeyHVUBHXRYARBAGR-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
  • 3p-methoxyflavonoid-skeleton
  • 3-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 8-hydroxyflavonoid
  • Flavone
  • 3-methoxychromone
  • Chromone
  • Dimethoxybenzene
  • Benzopyran
  • 1-benzopyran
  • O-dimethoxybenzene
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Phenoxy compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP2.78ALOGPS
logP2.4ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.64ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.04 m³·mol⁻¹ChemAxon
Polarizability37.43 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]+189.3931661259
DarkChem[M-H]-189.93131661259
DeepCCS[M+H]+187.6130932474
DeepCCS[M-H]-185.21430932474
DeepCCS[M-2H]-218.68230932474
DeepCCS[M+Na]+193.87430932474
AllCCS[M+H]+186.632859911
AllCCS[M+H-H2O]+183.532859911
AllCCS[M+NH4]+189.532859911
AllCCS[M+Na]+190.332859911
AllCCS[M-H]-188.932859911
AllCCS[M+Na-2H]-188.632859911
AllCCS[M+HCOO]-188.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,8-Dihydroxy-3,3',4',7-tetramethoxyflavoneCOC1=C(O)C2=C(C(O)=C1)C(=O)C(OC)=C(O2)C1=CC(OC)=C(OC)C=C15252.1Standard polar33892256
5,8-Dihydroxy-3,3',4',7-tetramethoxyflavoneCOC1=C(O)C2=C(C(O)=C1)C(=O)C(OC)=C(O2)C1=CC(OC)=C(OC)C=C13335.3Standard non polar33892256
5,8-Dihydroxy-3,3',4',7-tetramethoxyflavoneCOC1=C(O)C2=C(C(O)=C1)C(=O)C(OC)=C(O2)C1=CC(OC)=C(OC)C=C13292.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone,1TMS,isomer #1COC1=CC=C(C2=C(OC)C(=O)C3=C(O)C=C(OC)C(O[Si](C)(C)C)=C3O2)C=C1OC3230.5Semi standard non polar33892256
5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone,1TMS,isomer #2COC1=CC=C(C2=C(OC)C(=O)C3=C(O[Si](C)(C)C)C=C(OC)C(O)=C3O2)C=C1OC3316.2Semi standard non polar33892256
5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone,2TMS,isomer #1COC1=CC=C(C2=C(OC)C(=O)C3=C(O[Si](C)(C)C)C=C(OC)C(O[Si](C)(C)C)=C3O2)C=C1OC3187.9Semi standard non polar33892256
5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone,1TBDMS,isomer #1COC1=CC=C(C2=C(OC)C(=O)C3=C(O)C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1OC3465.5Semi standard non polar33892256
5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone,1TBDMS,isomer #2COC1=CC=C(C2=C(OC)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(O)=C3O2)C=C1OC3550.0Semi standard non polar33892256
5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone,2TBDMS,isomer #1COC1=CC=C(C2=C(OC)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1OC3662.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-052g-0309000000-b6443a02adb2bbb1ccee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone GC-MS (2 TMS) - 70eV, Positivesplash10-0uka-2122950000-5934a641ce3b74b1eba62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 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 - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 10V, Positive-QTOFsplash10-004i-0009000000-0d6874892ace13ff31452015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 20V, Positive-QTOFsplash10-004i-0009000000-5cf35d241d81466388682015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 40V, Positive-QTOFsplash10-0040-1958000000-f989211d8650731548e72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 10V, Negative-QTOFsplash10-00di-0009000000-e9a376de377c3f8563b52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 20V, Negative-QTOFsplash10-05fr-0009000000-c66eaeb32176a1e05a8f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 40V, Negative-QTOFsplash10-0fbi-1729000000-777a3af337c5f10471362015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 10V, Negative-QTOFsplash10-00di-0009000000-376f57cec159213863912021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 20V, Negative-QTOFsplash10-00di-0319000000-23be6a2632a5b81b0bba2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 40V, Negative-QTOFsplash10-00li-1921000000-b3f53e795cf71ed8d38f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 10V, Positive-QTOFsplash10-004i-0009000000-15f06bca4340439c6e172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 20V, Positive-QTOFsplash10-004i-0009000000-38c2465d114de1cb69542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3,3',4',7-tetramethoxyflavone 40V, Positive-QTOFsplash10-001i-2915000000-4c6d473c7e179b0ebcef2021-09-24Wishart 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 IDFDB002507
KNApSAcK IDC00004739
Chemspider ID10577440
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12289982
PDB IDNot Available
ChEBI ID222101
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.. .