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Showing Compound Nobiletin (FDB000683)

Record Information
Version1.0
Creation date2010-04-08 22:04:40 UTC
Update date2020-02-24 19:10:12 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. 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. Based on a literature review a significant number of articles have been published on Nobiletin.
CAS Number478-01-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNobiletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dr-0109000000-1083a97d47bd665e7e3eSpectrum
Predicted GC-MSNobiletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNobiletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0001900000-33c32e9e66704097c76a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kb-4930000000-6905f538e3d50304566b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06rf-0039000000-1f10f3c85ebc9576e9e82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-ec4f0760bcd6e1c1fcec2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-a07fe56ebf78505155132017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dr-0009000000-f517eba98f7a9c2ef6dc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-26380311919f21cc12642017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-a1ea51facc9a617005d92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-ed668e0372bef20e7e1e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0003900000-abbce9b6fc298b405ea62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0uki-0009600000-6e113107c7038d9754bf2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-c7bb5f00231de50384482017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0017900000-76a74f58aaa8107742e62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0001900000-33c32e9e66704097c76a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1449000000-515986740b5064496d802017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0001900000-27af360ec486a6c3d9c32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0fki-0009200000-4319c91ac3c4b550666e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0009700000-3eec55e1b3cc7eef561a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0129000000-56a5cc483729ca41cd8c2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-4cb76fd70e9da24d2d792015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0001900000-1e46aabd07d48fdf18122015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ml-0249000000-571e1067224eee3521402015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-7349cf45f0a975c8fa0d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0006900000-635ddb31cf10fc1ba6872015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rl-0169000000-608732c8f7b6ff2359742015-04-25View Spectrum
NMRNot Available
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 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.DUKE
Anti histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.DUKE
Anti-proliferativeAn agent that inhibits cell growth and division, particularly in cancer cells, preventing tumor expansion. It plays a biological role in regulating cell cycles and has therapeutic applications in cancer treatment, such as chemotherapy and targeted therapy, with key medical uses in managing various types of cancer and other proliferative diseases.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Cholinergic38323 An agent that stimulates the parasympathetic nervous system by mimicking acetylcholine, enhancing muscle contraction, and regulating various bodily functions. Therapeutically, it treats conditions like glaucoma, myasthenia gravis, and Alzheimer's disease, improving muscle tone, cognition, and eye pressure.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
FungistatAn agent that inhibits fungal growth, used to prevent fungal infections, commonly applied in therapeutic applications such as treating skin and nail infections, and managing fungal diseases in immunocompromised patients.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.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.