Showing Compound Tangeritin (FDB002412)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:22 UTC

Update date

2020-02-24 19:10:29 UTC

Primary ID

FDB002412

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Tangeritin

Description

Tangeritin 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, tangeritin is considered to be a flavonoid. Tangeritin is a bitter tasting compound. Tangeritin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Tangeritin has also been detected, but not quantified in, several different foods, such as lemons (Citrus limon), fruits, broccolis (Brassica oleracea var. italica), mandarin orange (clementine, tangerine), and sweet bays (Laurus nobilis). This could make tangeritin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Tangeritin.

CAS Number

481-53-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4',5,6,7,8-Pentamethoxyflavone	ChEBI
5,6,7,8,4'-Pentamethoxyflavone	ChEBI
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Tangeritin	ChEBI
4',5,6,7,8-Pentamethoxy-flavone	HMDB, MeSH
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4-benzopyrone	HMDB
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one	HMDB
Flavone, 4',5,6,7,8-pentamethoxy- (7ci,8ci)	HMDB
Flavone, 5,6,7,8,4'-pentamethoxy	HMDB
Pentamethoxyflavone	HMDB
Ponkanetin	HMDB
Tangeretin (6ci)	HMDB
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CI	db_source
5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one	biospider
Flavone, 4',5,6,7,8-pentamethoxy-	biospider
Flavone, 4',5,6,7,8-pentamethoxy- (7CI,8CI)	biospider
Tangeretin	db_source
Tangeretin (6CI)	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.0093 g/L	ALOGPS
logP	2.88	ALOGPS
logP	2.18	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	15.26	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.29 m³·mol⁻¹	ChemAxon
Polarizability	38.8 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

C20H20O7

IUPAC name

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

InChI Identifier

InChI=1S/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3

InChI Key

ULSUXBXHSYSGDT-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1

Average Molecular Weight

372.3686

Monoisotopic Molecular Weight

372.120902994

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

4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
Flavone
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pentamethoxyflavone (CHEBI:9400 )
flavones (C10190 )
Flavones and Flavonols (C10190 )
Flavones and Flavonols (LMPK12111443 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Plant

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 64.51%; H 5.41%; O 30.08%	DFC
Melting Point	Mp 154°	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	Tangeritin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-0229000000-e6e9ad7413b10f4d2f60	Spectrum
Predicted GC-MS	Tangeritin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0udi-0009000000-ee2b46e43857d53e36ea	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0ue9-0958000000-95f79379a8770cf234f4	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0952000000-385e0c59e575279d1929	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0962000000-4ce20f8bebfb893364c7	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0950000000-e79b83fbcdc12ca4342b	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0972000000-83a368b34c5d8037313d	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0f6t-0092000000-92f00f21de9842c77822	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-a7c011cb08d063f98b3f	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-a7c8c2980e91305fecf4	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-5acd0f1ad174af992dfb	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000t-0009000000-35763dc54f1cba9960fd	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-557dbb4d489762f5c6c4	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-e5388c8cb4caef8a8398	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-052f-0009000000-59afa2bdabbf2a62b6ee	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-8f99cd4efaf456f16bd1	Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-0579000000-a6a3232db05025b3a8ec	Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-0359000000-37d7e88884dbac30de10	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0489000000-2315290c34940c8911af	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-006x-0009000000-ade42d3073bd96a1c4e1	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-af49c5c40b1713ce986a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0009000000-ed0776ee5a241620324c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-0249000000-1ea96f27298b5874e53b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-297810d36d9613c636c8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0009000000-f9cba6ad31aa4a2c1f91	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-1269000000-2c95b789a68359ce6e70	Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

9400

Phenol-Explorer ID

238

DrugBank ID

Not Available

HMDB ID

HMDB30539

CRC / DFC (Dictionary of Food Compounds) ID

CLQ65-R:CLQ65-R

EAFUS ID

Not Available

Dr. Duke ID

TANGERITIN|TANGERETIN|PONKANETIN

BIGG ID

Not Available

KNApSAcK ID

C00001105

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

Not Available

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 lymphocytic			DUKE
anti metastatic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti mutagenic			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti proliferant			DUKE
apoptotic			DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
ERK1 inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
ERK2 inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hypolipidemic			DUKE
multidrug resistance inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
neuroprotective	63726	Any compound that can be used for the treatment of neurodegenerative disorders.	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

— 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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.