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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:04 UTC
Update Date2022-03-07 02:52:12 UTC
HMDB IDHMDB0029545
Secondary Accession Numbers
  • HMDB29545
Metabolite Identification
Common Name3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone
Description3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 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, 3'-hydroxy-4',5,6,7,8-pentamethoxyflavone is considered to be a flavonoid. 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone has been detected, but not quantified in, citrus and mandarin orange (clementine, tangerine). This could make 3'-hydroxy-4',5,6,7,8-pentamethoxyflavone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone.
Structure
Data?1582753434
Synonyms
ValueSource
3'-DemethylnobiletinChEMBL, HMDB
3'-Hydroxy-5,6,7,8,4'-pentamethoxyflavoneHMDB
Chemical FormulaC20H20O8
Average Molecular Weight388.368
Monoisotopic Molecular Weight388.115817616
IUPAC Name2-(3-hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one
Traditional Name2-(3-hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
CAS Registry Number112448-39-2
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC
InChI Identifier
InChI=1S/C20H20O8/c1-23-13-7-6-10(8-11(13)21)14-9-12(22)15-16(24-2)18(25-3)20(27-5)19(26-4)17(15)28-14/h6-9,21H,1-5H3
InChI KeyXFYYZBJXMSDKCV-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
  • 7-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 5-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • Flavone
  • Hydroxyflavonoid
  • Monohydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Methoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous ester
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Point139 - 140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility29.52 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP2.84ALOGPS
logP1.88ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.55ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area92.68 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.27 m³·mol⁻¹ChemAxon
Polarizability39.68 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]+190.3831661259
DarkChem[M-H]-192.99631661259
DeepCCS[M+H]+184.40430932474
DeepCCS[M-H]-182.04630932474
DeepCCS[M-2H]-215.79630932474
DeepCCS[M+Na]+190.99830932474
AllCCS[M+H]+190.632859911
AllCCS[M+H-H2O]+187.732859911
AllCCS[M+NH4]+193.432859911
AllCCS[M+Na]+194.232859911
AllCCS[M-H]-194.132859911
AllCCS[M+Na-2H]-194.132859911
AllCCS[M+HCOO]-194.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3'-Hydroxy-4',5,6,7,8-pentamethoxyflavoneCOC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC5020.6Standard polar33892256
3'-Hydroxy-4',5,6,7,8-pentamethoxyflavoneCOC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC3342.0Standard non polar33892256
3'-Hydroxy-4',5,6,7,8-pentamethoxyflavoneCOC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC3315.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone,1TMS,isomer #1COC1=CC=C(C2=CC(=O)C3=C(OC)C(OC)=C(OC)C(OC)=C3O2)C=C1O[Si](C)(C)C3277.0Semi standard non polar33892256
3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone,1TBDMS,isomer #1COC1=CC=C(C2=CC(=O)C3=C(OC)C(OC)=C(OC)C(OC)=C3O2)C=C1O[Si](C)(C)C(C)(C)C3482.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi0-0109000000-52d1ad862e85b8b16d7c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone GC-MS (1 TMS) - 70eV, Positivesplash10-0002-1013900000-6e53d34391614f48d49c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 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'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 10V, Negative-QTOFsplash10-000i-0009000000-07ea1466af753fcc9c192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 20V, Negative-QTOFsplash10-000i-0009000000-0e0de0c3783fb221044d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 40V, Negative-QTOFsplash10-059f-0049000000-b28359ff34e2bbc5f9142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 10V, Negative-QTOFsplash10-000i-0009000000-2acd9d3ff7494eb530ed2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 20V, Negative-QTOFsplash10-007c-0009000000-cae272e33c4422eba5622021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 10V, Positive-QTOFsplash10-000i-0009000000-d465ec0e71a716a507682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 20V, Positive-QTOFsplash10-000i-0009000000-0964af7d5aeba28aab912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 40V, Positive-QTOFsplash10-006x-4449000000-8434411cb9295a243ab22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 10V, Positive-QTOFsplash10-000i-0009000000-ede85f82b500aeed4a152021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 20V, Positive-QTOFsplash10-000i-0009000000-58f827296f0b35ad1cee2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxy-4',5,6,7,8-pentamethoxyflavone 40V, Positive-QTOFsplash10-00r2-0109000000-0301e1b15b943ca9e7172021-09-24Wishart 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 IDFDB000690
KNApSAcK IDC00003935
Chemspider ID159521
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound183466
PDB IDNot Available
ChEBI ID479535
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1810361
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.. .