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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:02 UTC
Update Date2020-02-26 21:43:53 UTC
HMDB IDHMDB0029540
Secondary Accession Numbers
  • HMDB29540
Metabolite Identification
Common NameNobiletin
DescriptionNobiletin 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, nobiletin is considered to be a flavonoid. Nobiletin is a bitter tasting compound. Nobiletin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Nobiletin has also been detected, but not quantified in, several different foods, such as citrus, grapefruits (Citrus X paradisi), lemons (Citrus limon), mandarin orange (clementine, tangerine), and sweet bays (Laurus nobilis). This could make nobiletin a potential biomarker for the consumption of these foods. Nobiletin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Nobiletin.
Structure
Data?1582753433
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 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
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point134 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M+H]+ExperimentalNot Available191.253http://allccs.zhulab.cn/database/detail?ID=AllCCS00001479
DarkChem[M+H]+PredictedNot Available196.90431661259
DarkChem[M-H]-PredictedNot Available197.23231661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0109000000-1083a97d47bd665e7e3e2017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0001900000-33c32e9e66704097c76a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kb-4930000000-6905f538e3d50304566b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06rf-0039000000-1f10f3c85ebc9576e9e82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-ec4f0760bcd6e1c1fcec2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-a07fe56ebf78505155132017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dr-0009000000-f517eba98f7a9c2ef6dc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-26380311919f21cc12642017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-a1ea51facc9a617005d92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-ed668e0372bef20e7e1e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0003900000-abbce9b6fc298b405ea62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0uki-0009600000-6e113107c7038d9754bf2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-c7bb5f00231de50384482017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0017900000-76a74f58aaa8107742e62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0001900000-33c32e9e66704097c76a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1449000000-515986740b5064496d802017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-4cb76fd70e9da24d2d792015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0001900000-1e46aabd07d48fdf18122015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ml-0249000000-571e1067224eee3521402015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-7349cf45f0a975c8fa0d2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0006900000-635ddb31cf10fc1ba6872015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rl-0169000000-608732c8f7b6ff2359742015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-e6676db6ac5226430fd92021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-0009700000-50d8ee8d708b57fa4ba52021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-3ecd8c89d3cf771412502021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0001900000-761c55d2f2478f1e1ef52021-09-08View 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 ID237
FooDB 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 ID7602
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB 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.. .