ChemFOnt: Showing chemical card for Quercetin 3-O-caffeyl-glucoside (CFc000282012)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:57 UTC

Chemfont ID

CFc000282012

Molecule Identification

Common Name

Quercetin 3-O-caffeyl-glucoside

Definition

Quercetin 3-o-caffeyl-glucoside is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Quercetin 3-o-caffeyl-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Quercetin 3-o-caffeyl-glucoside can be found in caraway, which makes quercetin 3-o-caffeyl-glucoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₃₀H₂₆O₁₅

Average Molecular Weight

626.5184

Monoisotopic Molecular Weight

626.127170162

IUPAC Name

[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

None

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)O[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H26O15/c31-14-9-19(36)23-20(10-14)43-28(13-3-5-16(33)18(35)8-13)29(25(23)39)45-30-27(41)26(40)24(38)21(44-30)11-42-22(37)6-2-12-1-4-15(32)17(34)7-12/h1-10,21,24,26-27,30-36,38,40-41H,11H2/b6-2+/t21-,24-,26+,27-,30+/m1/s1

InChI Key

IHBVMUCQCZEAPW-PFNFWJRHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 3-O-p-coumaroyl glycosides

Alternative Parents

Substituents

Flavonoid 3-o-6-p-coumaroyl-glycoside
Flavonoid-3-o-glycoside
Flavone
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Chromone
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Pyranone
Benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Fatty acyl
Pyran
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302496)

Food

Herb and spice

Spice

Caraway (FooDB: FOOD00043)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	2.58	ALOGPS
logP	2.28	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	253.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	152.8 m³·mol⁻¹	ChemAxon
Polarizability	60.52 Å³	ChemAxon
Number of Rings	5	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

HMDB0302496

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004800

KNApSAcK ID

Not Available

Chemspider ID

8207461

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10031891

PDB ID

Not Available

ChEBI ID

141137

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Quercetin 3-O-caffeyl-glucoside (CFc000282012)

MOL for CFc000282012 (Quercetin 3-O-caffeyl-glucoside)

3D MOL for CFc000282012 (Quercetin 3-O-caffeyl-glucoside)

3D SDF for CFc000282012 (Quercetin 3-O-caffeyl-glucoside)

3D-SDF for CFc000282012 (Quercetin 3-O-caffeyl-glucoside)

PDB for CFc000282012 (Quercetin 3-O-caffeyl-glucoside)

3D PDB for CFc000282012 (Quercetin 3-O-caffeyl-glucoside)

SMILES for CFc000282012 (Quercetin 3-O-caffeyl-glucoside)

INCHI for CFc000282012 (Quercetin 3-O-caffeyl-glucoside)

Structure for CFc000282012 (Quercetin 3-O-caffeyl-glucoside)

3D Structure for CFc000282012 (Quercetin 3-O-caffeyl-glucoside)