Showing Compound Quercetagetin (FDB011897)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:53 UTC

Update date

2020-02-24 19:11:05 UTC

Primary ID

FDB011897

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Quercetagetin

Description

2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one, also known as 6-hydroxyquercetin or 3,3',4',5,6,7-hexahydroxyflavone, is a member of the class of compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one can be synthesized from quercetin. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, axillarin, eupatin, and patuletin. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is a bitter tasting compound found in sweet orange, which makes 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one a potential biomarker for the consumption of this food product.

CAS Number

90-18-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-(3,4-Dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4-benzopyrone	ChEBI
3,3',4',5,6,7-Hexahydroxyflavone	ChEBI
6-Hydroxyquercetin	ChEBI
3,5,6,7,3',4'-Hexamethoxyflavone	MeSH
3,5,6,7-Tetrahydroxy-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one	MeSH
Quercetogetin	MeSH
2-(3,4-Dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4H-1-benzopyran-4-one, 9CI	db_source
3',4',5,6,7-Pentahydroxyflavonol	db_source
Quercetagetin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	1.7	ALOGPS
logP	1.85	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.56	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.84 m³·mol⁻¹	ChemAxon
Polarizability	29.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H10O8

IUPAC name

2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4H-chromen-4-one

InChI Identifier

InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)15-14(22)13(21)10-9(23-15)4-8(18)11(19)12(10)20/h1-4,16-20,22H

InChI Key

ZVOLCUVKHLEPEV-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC2=C(C(O)=C1O)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C=C1

Average Molecular Weight

318.2351

Monoisotopic Molecular Weight

318.037567296

Classification

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
6-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavonols (CHEBI:8695 )
hexahydroxyflavone (CHEBI:8695 )
flavonols (C10122 )
Flavones and Flavonols (C10122 )
Flavones and Flavonols (LMPK12112983 )

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 56.61%; H 3.17%; O 40.22%	DFC
Melting Point	Not Available
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	361 (e 21877) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Quercetagetin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0900-1212109000-3d0cb1e71bc3f80f051e	Spectrum
Predicted GC-MS	Quercetagetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f79-0792000000-663986ef797f12ea62e8	Spectrum
Predicted GC-MS	Quercetagetin, 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-QFT 22V, positive	splash10-01b9-0397000000-9ad48bd249a3aa567ce0	2020-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 22V, positive	splash10-0g4j-0492000000-c7770d50d16d1d0b8084	2020-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-e0804a88f8274e655f90	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0349000000-4d74a79028a275bf77d7	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0l6r-4920000000-691c34c0f5798b9cc754	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0119000000-1642b5f1d7c819f7c757	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0479000000-ed9d9b0a589026bce21b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xr-7940000000-0ef9c3a3a5bb3639b66c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-4329fbc3ab22500675af	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0619000000-3882a151bd0697d162f2	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06di-1920000000-e89690a0c34929e973b8	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-9dd1047022f2116af963	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0009000000-c73aca74b75a03dfe2c4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1912000000-282b925a12b2ab6547aa	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

354

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HBP96-H:HBP96-H

EAFUS ID

Not Available

Dr. Duke ID

QUERCETAGETIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

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
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	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
dye	37958		DUKE
HIV-reverse-transcriptase 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
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).