Showing Compound Isosinensetin (FDB016709)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:36 UTC

Update date

2019-11-26 03:13:39 UTC

Primary ID

FDB016709

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Isosinensetin

Description

Isosinensetin 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, isosinensetin is considered to be a flavonoid. Isosinensetin has been detected, but not quantified in, several different foods, such as citrus, fruits, mandarin orange (clementine, tangerine), and sweet oranges (Citrus sinensis). This could make isosinensetin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isosinensetin.

CAS Number

17290-70-9

Structure

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

Synonyms

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Synonym	Source
2-(3,4-Dimethoxyphenyl)-5,7,8-trimethoxy-4H-1-benzopyran-4-one	HMDB
3',4',5,7,8-Pentamethoxyflavone	HMDB
5,7,8,3',4'-Pentamethoxyflavone	HMDB
5783'4'-Pentamethoxyflavone	ChEMBL, HMDB
6-Demethoxynobiletin	HMDB
Isosinensetin	db_source

Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0084 g/L	ALOGPS
logP	2.99	ALOGPS
logP	2.18	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	15.25	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	38.81 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

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

InChI Identifier

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

InChI Key

UYCWETIUOAGWIL-UHFFFAOYSA-N

Isomeric SMILES

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

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

3p-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
Flavone
Chromone
O-dimethoxybenzene
Dimethoxybenzene
Benzopyran
1-benzopyran
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Monocyclic benzene moiety
Vinylogous ester
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111403 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 64.51%; H 5.41%; O 30.08%	DFC
Melting Point	Mp 206-207°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Isosinensetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-0219000000-08268d7096bba0d0e29e	Spectrum
Predicted GC-MS	Isosinensetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isosinensetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-069fbf0e4eecf1da732e	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0009000000-e562c8188cfed501797b	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03du-1479000000-8930f9dcbc6832f2d415	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-dbb9247329632f027aa1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0009000000-8efa187824fc472aef59	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08gr-1295000000-47a4d29ba0d8a6deadb6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-aa9385dbb205bb238b88	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0009000000-005119c3fd0ac1eff959	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06sj-0249000000-546b7368652184854213	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-cef598d38b8dbae9b661	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05i0-0009000000-f174bc75cf6bee81dbda	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

548876

ChEMBL ID

CHEMBL451707

KEGG Compound ID

Not Available

Pubchem Compound ID

632135

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB37599

CRC / DFC (Dictionary of Food Compounds) ID

CNL34-W:KSN53-E

EAFUS ID

Not Available

Dr. Duke ID

ISOSINENSETIN

BIGG ID

Not Available

KNApSAcK ID

C00003912

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Isosinensetin (FDB016709)

Structure for FDB016709 (Isosinensetin)