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

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	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0ue9-0958000000-95f79379a8770cf234f4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0952000000-385e0c59e575279d1929	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0962000000-4ce20f8bebfb893364c7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0950000000-e79b83fbcdc12ca4342b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0972000000-83a368b34c5d8037313d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0f6t-0092000000-92f00f21de9842c77822	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-a7c011cb08d063f98b3f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-a7c8c2980e91305fecf4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-5acd0f1ad174af992dfb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000t-0009000000-35763dc54f1cba9960fd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-557dbb4d489762f5c6c4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-e5388c8cb4caef8a8398	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-052f-0009000000-59afa2bdabbf2a62b6ee	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4l-0009000000-8f99cd4efaf456f16bd1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-0579000000-a6a3232db05025b3a8ec	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-0359000000-37d7e88884dbac30de10	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0489000000-2315290c34940c8911af	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-006x-0009000000-ade42d3073bd96a1c4e1	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-af49c5c40b1713ce986a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0009000000-ed0776ee5a241620324c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-0249000000-1ea96f27298b5874e53b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-297810d36d9613c636c8	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0009000000-f9cba6ad31aa4a2c1f91	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-1269000000-2c95b789a68359ce6e70	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

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	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 histaminic	37956	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-lymphocytic		An antibody that targets T cells, used to prevent rejection in organ transplantation and treat autoimmune diseases by suppressing the immune system.	DUKE
Anti metastatic	35610	An agent that inhibits cancer cell spread, reducing tumor metastasis. It plays a biological role in blocking cell migration and invasion, and has therapeutic applications in cancer treatment. Key medical uses include preventing cancer recurrence and improving survival rates in patients with various types of cancer.	DUKE
Anti-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti proliferant		An agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.	DUKE
Apoptotic		An agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.	DUKE
Cancer preventive	35610	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
ERK1 inhibitor	23924	An agent that blocks the activity of ERK1, a key enzyme in cell signaling pathways, reducing cell proliferation and inflammation. Therapeutically, it has applications in cancer, neurodegenerative, and inflammatory diseases, with potential uses in treating tumors, Alzheimer's, and autoimmune disorders.	DUKE
ERK2 inhibitor	23924	An agent that blocks the activity of ERK2, a key enzyme in cell signaling pathways, reducing cell proliferation and inflammation. Therapeutically, it has applications in cancer, autoimmune diseases, and neurodegenerative disorders, with potential uses in treating tumors, multiple sclerosis, and Alzheimer's disease.	DUKE
Fungicide	24127	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
Hypolipidemic		An agent that lowers lipid levels, treating hyperlipidemias by reducing cholesterol and triglyceride production, with therapeutic applications in managing cardiovascular disease, atherosclerosis, and stroke, commonly used to prevent heart attacks and improve overall cardiovascular health.	DUKE
Multidrug resistance inhibitor	35222	An agent that blocks the efflux pumps in cancer cells, restoring sensitivity to chemotherapy drugs and overcoming drug resistance, commonly used in cancer treatment to enhance efficacy of anticancer medications.	DUKE
Neuroprotective	63726	An agent that protects nerve cells from damage or degeneration, reducing the risk of neurodegenerative diseases. Therapeutically, it helps manage conditions like Alzheimer's, Parkinson's, and stroke, promoting neuronal survival and function.	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.