Nobiletin (CHEM023269)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:56:22 UTC
Update Date2026-04-03 05:05:17 UTC
Accession NumberCHEM023269
Identification
Common NameNobiletin
ClassSmall Molecule
DescriptionA methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5,6,7,8,3',4'-HexamethoxyflavoneChEBI
HexamethoxyflavoneChEBI
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 Mass402.395 g/mol
Monoisotopic Mass402.131 g/mol
CAS Registry Number478-01-3
IUPAC Name2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one
Traditional Namenobiletin
SMILESCOC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC
InChI IdentifierInChI=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
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
  • 4p-methoxyflavonoid-skeleton
  • 5-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • Flavone
  • Chromone
  • Benzopyran
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Vinylogous ester
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0109000000-1083a97d47bd665e7e3eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0001900000-33c32e9e66704097c76aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kb-4930000000-6905f538e3d50304566bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06rf-0039000000-1f10f3c85ebc9576e9e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-ec4f0760bcd6e1c1fcecSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-a07fe56ebf7850515513Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dr-0009000000-f517eba98f7a9c2ef6dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-26380311919f21cc1264Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-a1ea51facc9a617005d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-ed668e0372bef20e7e1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0003900000-abbce9b6fc298b405ea6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0uki-0009600000-6e113107c7038d9754bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-c7bb5f00231de5038448Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0017900000-76a74f58aaa8107742e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0001900000-33c32e9e66704097c76aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1449000000-515986740b5064496d80Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0001900000-27af360ec486a6c3d9c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0fki-0009200000-4319c91ac3c4b550666eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0009700000-3eec55e1b3cc7eef561aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0129000000-56a5cc483729ca41cd8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-4cb76fd70e9da24d2d79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0001900000-1e46aabd07d48fdf1812Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ml-0249000000-571e1067224eee352140Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-7349cf45f0a975c8fa0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0006900000-635ddb31cf10fc1ba687Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rl-0169000000-608732c8f7b6ff235974Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029540
FooDB IDFDB000683
Phenol Explorer ID237
KNApSAcK IDC00001076
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNobiletin
Chemspider ID65283
ChEBI ID7602
PubChem Compound ID72344
Kegg Compound IDC10112
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=25488359
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25845666
3. 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.
4. 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.
5. 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.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.