Showing Compound Nobiletin (FDB000683)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:40 UTC

Update date

2020-02-24 19:10:12 UTC

Primary ID

FDB000683

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Nobiletin

Description

Nobiletin 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 Number

478-01-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
5,6,7,8,3',4'-Hexamethoxyflavone	ChEBI
Hexamethoxyflavone	ChEBI
2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9ci	HMDB
Flavone, 5,6,7,8,3',4'-hexamethoxy	HMDB
2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9CI	db_source
Nobiletin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.0092 g/L	ALOGPS
logP	2.62	ALOGPS
logP	2.02	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	15.13	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	81.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.75 m³·mol⁻¹	ChemAxon
Polarizability	41.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C21H22O8

IUPAC name

2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one

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 Key

MRIAQLRQZPPODS-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC

Average Molecular Weight

402.3946

Monoisotopic Molecular Weight

402.13146768

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyflavone (CHEBI:7602 )
flavones (C10112 )
Flavones and Flavonols (LMPK12111468 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Plant

Role

Industrial application:

Pharmaceutical industry:

Anti-inflammatory

Antineoplastic agent:

Antitumor

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 62.68%; H 5.51%; O 31.81%	DFC
Melting Point	Mp 134°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Nobiletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dr-0109000000-1083a97d47bd665e7e3e	Spectrum
Predicted GC-MS	Nobiletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nobiletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-0001900000-33c32e9e66704097c76a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00kb-4930000000-6905f538e3d50304566b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-06rf-0039000000-1f10f3c85ebc9576e9e8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0079-0009000000-ec4f0760bcd6e1c1fcec	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0079-0009000000-a07fe56ebf7850515513	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00dr-0009000000-f517eba98f7a9c2ef6dc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0079-0009000000-26380311919f21cc1264	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0079-0009000000-a1ea51facc9a617005d9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0079-0009000000-ed668e0372bef20e7e1e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0003900000-abbce9b6fc298b405ea6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0uki-0009600000-6e113107c7038d9754bf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0079-0009000000-c7bb5f00231de5038448	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-0017900000-76a74f58aaa8107742e6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-0001900000-33c32e9e66704097c76a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-1449000000-515986740b5064496d80	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0001900000-27af360ec486a6c3d9c3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0fki-0009200000-4319c91ac3c4b550666e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-0009700000-3eec55e1b3cc7eef561a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0129000000-56a5cc483729ca41cd8c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000900000-4cb76fd70e9da24d2d79	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0001900000-1e46aabd07d48fdf1812	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02ml-0249000000-571e1067224eee352140	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000900000-7349cf45f0a975c8fa0d	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0006900000-635ddb31cf10fc1ba687	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06rl-0169000000-608732c8f7b6ff235974	2015-04-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

237

DrugBank ID

Not Available

HMDB ID

HMDB29540

CRC / DFC (Dictionary of Food Compounds) ID

BFN32-P:BFN32-P

EAFUS ID

Not Available

Dr. Duke ID

NOBILETIN|NOBELITIN

BIGG ID

Not Available

KNApSAcK ID

C00001076

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Nobiletin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti histaminic	37956	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 proliferative			DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cholinergic	38323	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
fungicide	24127	A substance used to destroy fungal pests.	DUKE
fungistat			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	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

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not 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.