ChemFOnt: Showing chemical card for Quercetin 3-O-glucosyl-rhamnosyl-galactoside (CFc000332871)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:25 UTC

Chemfont ID

CFc000332871

Molecule Identification

Common Name

Quercetin 3-O-glucosyl-rhamnosyl-galactoside

Definition

Hyperin 6''-[glucosyl-(1->3)-rhamnoside], also known as Q-glu-rha-gal or quercetin-3-glu-rha-gal, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Hyperin 6''-[glucosyl-(1->3)-rhamnoside] is soluble (in water) and a very weakly acidic compound (based on its pKa). Hyperin 6''-[glucosyl-(1->3)-rhamnoside] can be found in tea, which makes hyperin 6''-[glucosyl-(1->3)-rhamnoside] a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Q-Glu-rha-gal	HMDB
Quercetin 3-glucosyl(1-3)rhamnosyl(1-6)galactoside	HMDB
Quercetin 3-glucosyl-(1->3)-rhamnosyl-(1->6)-galactoside	HMDB
Quercetin-3-glu-rha-gal	HMDB

Chemical Formula

C₃₃H₄₀O₂₁

Average Molecular Weight

772.6581

Monoisotopic Molecular Weight

772.206208342

IUPAC Name

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

Traditional Name

CAS Registry Number

134953-93-8

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O

InChI Identifier

InChI=1S/C33H40O21/c1-9-19(39)29(53-32-25(45)23(43)20(40)16(7-34)51-32)27(47)31(49-9)48-8-17-21(41)24(44)26(46)33(52-17)54-30-22(42)18-14(38)5-11(35)6-15(18)50-28(30)10-2-3-12(36)13(37)4-10/h2-6,9,16-17,19-21,23-27,29,31-41,43-47H,7-8H2,1H3/t9-,16+,17+,19-,20+,21-,23-,24-,25+,26+,27+,29+,31+,32-,33-/m0/s1

InChI Key

XEFNBVWDOQCMSG-GJHFDJSNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0039375)
Extracellular (HMDB: HMDB0039375)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039375)

Source

Exogenous

Exogenous (HMDB: HMDB0039375)

Food

Food (HMDB: HMDB0039375)

Tea

Tea (FooDB: FOOD00038)
Black tea (FooDB: FOOD00907)
Green tea (FooDB: FOOD00908)

Endogenous

Plant

Plant (HMDB: HMDB0039375)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039375)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	10.4 g/L	ALOGPS
logP	-0.56	ALOGPS
logP	-2.6	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	344.67 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	172.56 m³·mol⁻¹	ChemAxon
Polarizability	71.82 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0039375

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5492482

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Quercetin 3-O-glucosyl-rhamnosyl-galactoside (CFc000332871)

MOL for CFc000332871 (Quercetin 3-O-glucosyl-rhamnosyl-galactoside)

3D MOL for CFc000332871 (Quercetin 3-O-glucosyl-rhamnosyl-galactoside)

3D SDF for CFc000332871 (Quercetin 3-O-glucosyl-rhamnosyl-galactoside)

3D-SDF for CFc000332871 (Quercetin 3-O-glucosyl-rhamnosyl-galactoside)

PDB for CFc000332871 (Quercetin 3-O-glucosyl-rhamnosyl-galactoside)

3D PDB for CFc000332871 (Quercetin 3-O-glucosyl-rhamnosyl-galactoside)

SMILES for CFc000332871 (Quercetin 3-O-glucosyl-rhamnosyl-galactoside)

INCHI for CFc000332871 (Quercetin 3-O-glucosyl-rhamnosyl-galactoside)

Structure for CFc000332871 (Quercetin 3-O-glucosyl-rhamnosyl-galactoside)

3D Structure for CFc000332871 (Quercetin 3-O-glucosyl-rhamnosyl-galactoside)