ChemFOnt: Showing chemical card for Quercetin 7-glucoside (CFc000281667)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:17 UTC

Chemfont ID

CFc000281667

Molecule Identification

Common Name

Quercetin 7-glucoside

Definition

Quercetin 7-glucoside, also known as quercimeritrin, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Quercetin 7-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Quercetin 7-glucoside can be found in a number of food items such as roman camomile, okra, dandelion, and cottonseed, which makes quercetin 7-glucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-3,5-dihydroxy-4H-1-benzopyran-4-one	ChEBI
3,5-Dihydroxy-2-(3,4-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-4H-1-benzopyran-4-one	ChEBI
Quercetin 7-O-glucoside	ChEBI
Quercimeritrin	ChEBI
Quercimeritroside	ChEBI
2-(3,4-Dihydroxyphenyl)-7-(b-D-glucopyranosyloxy)-3,5-dihydroxy-4H-1-benzopyran-4-one	Generator
2-(3,4-Dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-3,5-dihydroxy-4H-1-benzopyran-4-one	Generator
3,5-Dihydroxy-2-(3,4-dihydroxyphenyl)-7-(b-D-glucopyranosyloxy)-4H-1-benzopyran-4-one	Generator
3,5-Dihydroxy-2-(3,4-dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one	Generator
Quercetin 7-O-b-D-glucoside	Generator
Quercetin 7-O-β-D-glucoside	Generator
Quercetin 7-O-beta-D-glucoside	KEGG

Chemical Formula

C₂₁H₂₀O₁₂

Average Molecular Weight

464.3763

Monoisotopic Molecular Weight

464.095476104

IUPAC Name

2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

quercimeritrin

CAS Registry Number

491-50-9

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)31-8-4-11(25)14-12(5-8)32-20(18(29)16(14)27)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1

InChI Key

BBFYUPYFXSSMNV-HMGRVEAOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3-hydroxyflavone
Hydroxyflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
Benzopyran
1-benzopyran
Catechol
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:28529 )
monosaccharide derivative (CHEBI:28529 )
tetrahydroxyflavone (CHEBI:28529 )
flavonols (CHEBI:28529 )
quercetin O-glucoside (CHEBI:28529 )
flavonols (C12639 )
Flavones and Flavonols (C12639 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302151)

Cottonseed (FooDB: FOOD00341)
Sunflower (FooDB: FOOD00086)

Vegetable

Other vegetable

Okra (FooDB: FOOD00420)

Fruit

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Berry

Common grape (FooDB: FOOD00204)

Not Available

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0302151)

Anti herpetic (HMDB: HMDB0302151)
Insectiphile (HMDB: HMDB0302151)

Industrial application

Antiviral agent (HMDB: HMDB0302151)

Agriculture

Pesticide (HMDB: HMDB0302151)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.61 g/L	ALOGPS
logP	0.62	ALOGPS
logP	-0.11	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.98	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.01 m³·mol⁻¹	ChemAxon
Polarizability	43.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon