ChemFOnt: Showing chemical card for Malvidin 3-(6''-caffeoyl-glucoside) (CFc000281183)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:19 UTC

Chemfont ID

CFc000281183

Molecule Identification

Common Name

Malvidin 3-(6''-caffeoyl-glucoside)

Definition

Malvidin 3-(6''-caffeoyl-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. Malvidin 3-(6''-caffeoyl-glucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Malvidin 3-(6''-caffeoyl-glucoside) can be found in grape wine, which makes malvidin 3-(6''-caffeoyl-glucoside) a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₂H₃₁O₁₅

Average Molecular Weight

655.5795

Monoisotopic Molecular Weight

655.166295322

IUPAC Name

3-{[(3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

3-{[(3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium

CAS Registry Number

None

SMILES

[H][C@]1(COC(=O)\C=C\C2=CC(O)=C(O)C=C2)OC(OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(OC)=C(O)C(OC)=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C32H30O15/c1-42-22-8-15(9-23(43-2)27(22)38)31-24(12-17-19(35)10-16(33)11-21(17)45-31)46-32-30(41)29(40)28(39)25(47-32)13-44-26(37)6-4-14-3-5-18(34)20(36)7-14/h3-12,25,28-30,32,39-41H,13H2,1-2H3,(H4-,33,34,35,36,37,38)/p+1/t25-,28-,29+,30-,32?/m1/s1

InChI Key

LIEHUFTYLLDHTI-FCOFYTSKSA-O

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
Anthocyanin
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Dimethoxybenzene
M-dimethoxybenzene
Methoxyphenol
1-benzopyran
Benzopyran
Styrene
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Catechol
Phenol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Acetal
Polyol
Ether
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301667)

Food

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.056 g/L	ALOGPS
logP	3.31	ALOGPS
logP	3.3	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	238.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	170.73 m³·mol⁻¹	ChemAxon
Polarizability	63.93 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

HMDB0301667

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000055

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

87966935

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Malvidin 3-(6''-caffeoyl-glucoside) (CFc000281183)

MOL for CFc000281183 (Malvidin 3-(6''-caffeoyl-glucoside))

3D MOL for CFc000281183 (Malvidin 3-(6''-caffeoyl-glucoside))

3D SDF for CFc000281183 (Malvidin 3-(6''-caffeoyl-glucoside))

3D-SDF for CFc000281183 (Malvidin 3-(6''-caffeoyl-glucoside))

PDB for CFc000281183 (Malvidin 3-(6''-caffeoyl-glucoside))

3D PDB for CFc000281183 (Malvidin 3-(6''-caffeoyl-glucoside))

SMILES for CFc000281183 (Malvidin 3-(6''-caffeoyl-glucoside))

INCHI for CFc000281183 (Malvidin 3-(6''-caffeoyl-glucoside))

Structure for CFc000281183 (Malvidin 3-(6''-caffeoyl-glucoside))

3D Structure for CFc000281183 (Malvidin 3-(6''-caffeoyl-glucoside))