Record Information
Version1.0
Creation date2010-04-08 22:04:40 UTC
Update date2019-11-27 17:03:19 UTC
Primary IDFDB000683
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 lipid molecule. Nobiletin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Nobiletin is a bitter tasting compound. Nobiletin is found, on average, in the highest concentration in sweet oranges. Nobiletin has also been detected, but not quantified in, several different foods, such as citrus, grapefruits, lemons, mandarin orange (clementine, tangerine), and sweet bay. This could make nobiletin a potential biomarker for the consumption of these foods.
CAS Number478-01-3
Structure
Thumb
Synonyms
SynonymSource
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
2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9CIdb_source
Nobiletindb_source
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
Chemical FormulaC21H22O8
IUPAC name2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one
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
Isomeric SMILESCOC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC
Average Molecular Weight402.3946
Monoisotopic Molecular Weight402.13146768
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.68%; H 5.51%; O 31.81%DFC
Melting PointMp 134°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0109000000-1083a97d47bd665e7e3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0001900000-33c32e9e66704097c76aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kb-4930000000-6905f538e3d50304566bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06rf-0039000000-1f10f3c85ebc9576e9e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-ec4f0760bcd6e1c1fcecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-a07fe56ebf7850515513View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dr-0009000000-f517eba98f7a9c2ef6dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-26380311919f21cc1264View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-a1ea51facc9a617005d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-ed668e0372bef20e7e1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0003900000-abbce9b6fc298b405ea6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0uki-0009600000-6e113107c7038d9754bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-c7bb5f00231de5038448View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0017900000-76a74f58aaa8107742e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0001900000-33c32e9e66704097c76aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1449000000-515986740b5064496d80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-4cb76fd70e9da24d2d79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0001900000-1e46aabd07d48fdf1812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ml-0249000000-571e1067224eee352140View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-7349cf45f0a975c8fa0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0006900000-635ddb31cf10fc1ba687View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rl-0169000000-608732c8f7b6ff235974View in MoNA
ChemSpider ID65283
ChEMBL IDCHEMBL76447
KEGG Compound IDC10112
Pubchem Compound ID72344
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID237
DrugBank IDNot Available
HMDB IDHMDB29540
CRC / DFC (Dictionary of Food Compounds) IDBFN32-P:BFN32-P
EAFUS IDNot Available
Dr. Duke IDNOBILETIN|NOBELITIN
BIGG IDNot Available
KNApSAcK IDC00001076
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNobiletin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti proliferativeDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cholinergic38323 Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
fungistatDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.