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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:57:03 UTC
Update Date2022-03-07 02:55:27 UTC
HMDB IDHMDB0037689
Secondary Accession Numbers
  • HMDB37689
Metabolite Identification
Common Name3-Methoxynobiletin
Description3-Methoxynobiletin 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-methoxynobiletin is considered to be a flavonoid. 3-Methoxynobiletin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). 3-Methoxynobiletin has also been detected, but not quantified in, a few different foods, such as citrus, mandarin orange (clementine, tangerine), and sweet bays (Laurus nobilis). This could make 3-methoxynobiletin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Methoxynobiletin.
Structure
Data?1563863073
Synonyms
ValueSource
356783'4'-Heptamethoxy-flavoneChEMBL, HMDB
356783'4'-HeptamethoxyflavoneChEMBL, HMDB
2-(3,4-Dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-4H-1-benzopyran-4-oneHMDB
3,3',4',5,6,7,8-HeptamethoxyflavoneHMDB, MeSH
3,5,6,7,8,3',4'-HeptamethoxyflavoneHMDB, MeSH
3-HPTMFHMDB, MeSH
Hepta-3HMDB, MeSH
Chemical FormulaC22H24O9
Average Molecular Weight432.4206
Monoisotopic Molecular Weight432.142032366
IUPAC Name2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-4H-chromen-4-one
Traditional Name2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxychromen-4-one
CAS Registry Number1178-24-1
SMILES
COC1=C(OC)C=C(C=C1)C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1
InChI Identifier
InChI=1S/C22H24O9/c1-24-12-9-8-11(10-13(12)25-2)16-19(27-4)15(23)14-17(26-3)20(28-5)22(30-7)21(29-6)18(14)31-16/h8-10H,1-7H3
InChI KeySSXJHQZOHUYEGD-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
  • 5-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • Flavone
  • 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 ester
  • 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
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point129 - 131 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility35.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP2.39ALOGPS
logP1.89ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area90.91 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity112.47 m³·mol⁻¹ChemAxon
Polarizability44.46 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]+202.63231661259
DarkChem[M-H]-199.59531661259
DeepCCS[M+H]+195.45130932474
DeepCCS[M-H]-193.09330932474
DeepCCS[M-2H]-226.5830932474
DeepCCS[M+Na]+201.80830932474
AllCCS[M+H]+201.032859911
AllCCS[M+H-H2O]+198.332859911
AllCCS[M+NH4]+203.432859911
AllCCS[M+Na]+204.132859911
AllCCS[M-H]-207.232859911
AllCCS[M+Na-2H]-207.632859911
AllCCS[M+HCOO]-208.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-MethoxynobiletinCOC1=C(OC)C=C(C=C1)C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O14851.4Standard polar33892256
3-MethoxynobiletinCOC1=C(OC)C=C(C=C1)C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O13448.2Standard non polar33892256
3-MethoxynobiletinCOC1=C(OC)C=C(C=C1)C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O13372.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxynobiletin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-0111900000-56aafa7da90300449bc42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxynobiletin 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-Methoxynobiletin 10V, Positive-QTOFsplash10-001i-0000900000-afc884c59644724f867c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 20V, Positive-QTOFsplash10-001i-0000900000-f9de4ae450473c3b458d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 40V, Positive-QTOFsplash10-0gvp-1189400000-5a0962597f7a45e19d3c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 10V, Negative-QTOFsplash10-001i-0000900000-bbeffe042f922d4c41382015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 20V, Negative-QTOFsplash10-001i-0004900000-0039d36c395f01f6dd292015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 40V, Negative-QTOFsplash10-000l-1649100000-e7b7e5d526a801065a7c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 10V, Negative-QTOFsplash10-001i-0000900000-df00a544a62ec05d4b712021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 20V, Negative-QTOFsplash10-001i-0031900000-33292b5a349c5c80ca9b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 40V, Negative-QTOFsplash10-059i-2893100000-5c6e4003d472555728752021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 10V, Positive-QTOFsplash10-001i-0000900000-720979c2783234cdf4352021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 20V, Positive-QTOFsplash10-001i-0000900000-2cb83ccb9cf961d1222b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxynobiletin 40V, Positive-QTOFsplash10-00l6-1091300000-f828706b09ab8ca4470e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 ID392
FooDB IDFDB016817
KNApSAcK IDC00004804
Chemspider ID132996
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150893
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1863231
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.. .