ChemFOnt: Showing chemical card for Malvidin 3-(6''-p-coumarylglucoside) (CFc000281419)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:47 UTC

Chemfont ID

CFc000281419

Molecule Identification

Common Name

Malvidin 3-(6''-p-coumarylglucoside)

Definition

Malvidin 3-(6''-p-coumarylglucoside) 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''-p-coumarylglucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Malvidin 3-(6''-p-coumarylglucoside) can be synthesized from cis-4-coumaric acid. Malvidin 3-(6''-p-coumarylglucoside) can also be synthesized into malvidin. Malvidin 3-(6''-p-coumarylglucoside) can be found in common grape and grape, which makes malvidin 3-(6''-p-coumarylglucoside) a potential biomarker for the consumption of these food products. Malvidin 3-(6''-p-coumarylglucoside) may be a unique S.cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Malvidin-3-O-(6-O-cis-p-coumaryl-beta-D-glucoside)	ChEBI
Malvidin-3-O-(6-O-cis-p-coumaryl-b-D-glucoside)	Generator
Malvidin-3-O-(6-O-cis-p-coumaryl-β-D-glucoside)	Generator

Chemical Formula

C₃₂H₃₁O₁₄

Average Molecular Weight

639.5801

Monoisotopic Molecular Weight

639.1713807

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

Traditional Name

5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

CAS Registry Number

156577-22-9

SMILES

COC1=CC(=CC(OC)=C1O)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O)=CC(O)=C2

InChI Identifier

InChI=1S/C32H30O14/c1-41-22-9-16(10-23(42-2)27(22)37)31-24(13-19-20(35)11-18(34)12-21(19)44-31)45-32-30(40)29(39)28(38)25(46-32)14-43-26(36)8-5-15-3-6-17(33)7-4-15/h3-13,25,28-30,32,38-40H,14H2,1-2H3,(H3-,33,34,35,36,37)/p+1/t25-,28-,29+,30-,32-/m1/s1

InChI Key

HXQOVGDXCHFLOP-KWNZYCHBSA-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
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Cinnamic acid or derivatives
Glycosyl compound
O-glycosyl compound
Dimethoxybenzene
M-dimethoxybenzene
1-benzopyran
Methoxyphenol
Benzopyran
Phenoxy compound
Phenol ether
Styrene
Anisole
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
Phenol
Fatty acid ester
1-hydroxy-2-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

aromatic ether (CHEBI:75691 )
beta-D-glucoside (CHEBI:75691 )
anthocyanin cation (CHEBI:75691 )
cinnamate ester (CHEBI:75691 )
polyphenol (CHEBI:75691 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301903)

Food

Fruit

Berry

Grape (FooDB: FOOD00369)
Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	3.41	ALOGPS
logP	3.58	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	217.97 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	168.75 m³·mol⁻¹	ChemAxon
Polarizability	64.11 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

HMDB0301903

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001593

KNApSAcK ID

Not Available

Chemspider ID

30779237

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

75691

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Malvidin 3-(6''-p-coumarylglucoside) (CFc000281419)

MOL for CFc000281419 (Malvidin 3-(6''-p-coumarylglucoside))

3D MOL for CFc000281419 (Malvidin 3-(6''-p-coumarylglucoside))

3D SDF for CFc000281419 (Malvidin 3-(6''-p-coumarylglucoside))

3D-SDF for CFc000281419 (Malvidin 3-(6''-p-coumarylglucoside))

PDB for CFc000281419 (Malvidin 3-(6''-p-coumarylglucoside))

3D PDB for CFc000281419 (Malvidin 3-(6''-p-coumarylglucoside))

SMILES for CFc000281419 (Malvidin 3-(6''-p-coumarylglucoside))

INCHI for CFc000281419 (Malvidin 3-(6''-p-coumarylglucoside))

Structure for CFc000281419 (Malvidin 3-(6''-p-coumarylglucoside))

3D Structure for CFc000281419 (Malvidin 3-(6''-p-coumarylglucoside))