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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:02 UTC
Update Date2019-07-23 06:04:19 UTC
HMDB IDHMDB0029540
Secondary Accession Numbers
  • HMDB29540
Metabolite Identification
Common NameNobiletin
DescriptionNobiletin is found in citrus. Nobiletin is isolated from peel of king orange (Citrus nobilis), seville orange (Citrus aurantium) and other Citrus species, and the round kumquat (Fortunella japonica
Structure
Data?1563861859
Synonyms
ValueSource
HexamethoxyflavoneKegg
5,6,7,8,3',4'-HexamethoxyflavoneKegg
2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9ciHMDB
Flavone, 5,6,7,8,3',4'-hexamethoxyHMDB
Chemical FormulaC21H22O8
Average Molecular Weight402.3946
Monoisotopic Molecular Weight402.13146768
IUPAC Name2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one
Traditional Namenobiletin
CAS Registry Number478-01-3
SMILES
COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC
InChI Identifier
InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3
InChI KeyMRIAQLRQZPPODS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 8-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 5-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 3p-methoxyflavonoid-skeleton
  • Flavone
  • Chromone
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • 1-benzopyran
  • Benzopyran
  • Hydroxyquinol derivative
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Pyranone
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous ester
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0092 g/LALOGPS
logP2.62ALOGPS
logP2.02ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)15.13ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area81.68 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.75 m³·mol⁻¹ChemAxon
Polarizability41.79 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0109000000-1083a97d47bd665e7e3eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0001900000-33c32e9e66704097c76aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kb-4930000000-6905f538e3d50304566bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06rf-0039000000-1f10f3c85ebc9576e9e8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-ec4f0760bcd6e1c1fcecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-a07fe56ebf7850515513JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dr-0009000000-f517eba98f7a9c2ef6dcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-26380311919f21cc1264JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-a1ea51facc9a617005d9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-ed668e0372bef20e7e1eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0003900000-abbce9b6fc298b405ea6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0uki-0009600000-6e113107c7038d9754bfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-c7bb5f00231de5038448JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0017900000-76a74f58aaa8107742e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0001900000-33c32e9e66704097c76aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1449000000-515986740b5064496d80JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-4cb76fd70e9da24d2d79JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0001900000-1e46aabd07d48fdf1812JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ml-0249000000-571e1067224eee352140JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-7349cf45f0a975c8fa0dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0006900000-635ddb31cf10fc1ba687JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rl-0169000000-608732c8f7b6ff235974JSpectraViewer | MoNA
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 ID237
FoodDB IDFDB000683
KNApSAcK IDC00001076
Chemspider ID65283
KEGG Compound IDC10112
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNobiletin
METLIN IDNot Available
PubChem Compound72344
PDB IDNot Available
ChEBI ID221290
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kunimasa K, Ikekita M, Sato M, Ohta T, Yamori Y, Ikeda M, Kuranuki S, Oikawa T: Nobiletin, a citrus polymethoxyflavonoid, suppresses multiple angiogenesis-related endothelial cell functions and angiogenesis in vivo. Cancer Sci. 2010 Nov;101(11):2462-9. doi: 10.1111/j.1349-7006.2010.01668.x. [PubMed:20670297 ]
  2. Miyata Y, Sato T, Yano M, Ito A: Activation of protein kinase C betaII/epsilon-c-Jun NH2-terminal kinase pathway and inhibition of mitogen-activated protein/extracellular signal-regulated kinase 1/2 phosphorylation in antitumor invasive activity induced by the polymethoxy flavonoid, nobiletin. Mol Cancer Ther. 2004 Jul;3(7):839-47. [PubMed:15252145 ]
  3. Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71. [PubMed:12787887 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .