ChemFOnt: Showing chemical card for Malvidin 3-caffeoyl-glucoside (CFc000282581)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:04 UTC

Chemfont ID

CFc000282581

Molecule Identification

Common Name

Malvidin 3-caffeoyl-glucoside

Definition

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₄H₃₃O₁₃

Average Molecular Weight

649.618

Monoisotopic Molecular Weight

649.192116142

IUPAC Name

3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3-ethenyl-5-methoxy-4-methylphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

Traditional Name

3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3-ethenyl-5-methoxy-4-methylphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C34H32O13/c1-4-18-10-19(11-25(43-3)16(18)2)33-27(14-21-23(37)12-20(35)13-26(21)45-33)46-34-32(42)31(41)30(40)28(47-34)15-44-29(39)8-6-17-5-7-22(36)24(38)9-17/h4-14,28,30-32,34,40-42H,1,15H2,2-3H3,(H3-,35,36,37,38,39)/p+1/t28-,30-,31+,32-,34-/m1/s1

InChI Key

CTCAOGTXDRBMPF-UAWCLUNRSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position 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

Anthocyanidin 3-O-6-p-coumaroyl glycosides

Alternative Parents

Substituents

Anthocyanidin 3-o-6-p-coumaroyl-glycoside
Anthocyanidin-3-o-glycoside
Anthocyanin
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Styrene
Phenoxy compound
Catechol
Phenol ether
Methoxybenzene
Anisole
1-hydroxy-4-unsubstituted benzenoid
Toluene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Alkyl aryl ether
Monocyclic benzene moiety
Oxane
Fatty acyl
Monosaccharide
Benzenoid
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Carbonyl group
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303065)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	3.81	ALOGPS
logP	5.2	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	208.74 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	177.02 m³·mol⁻¹	ChemAxon
Polarizability	66.65 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

HMDB0303065

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007581

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Malvidin 3-caffeoyl-glucoside (CFc000282581)

MOL for CFc000282581 (Malvidin 3-caffeoyl-glucoside)

3D MOL for CFc000282581 (Malvidin 3-caffeoyl-glucoside)

3D SDF for CFc000282581 (Malvidin 3-caffeoyl-glucoside)

3D-SDF for CFc000282581 (Malvidin 3-caffeoyl-glucoside)

PDB for CFc000282581 (Malvidin 3-caffeoyl-glucoside)

3D PDB for CFc000282581 (Malvidin 3-caffeoyl-glucoside)

SMILES for CFc000282581 (Malvidin 3-caffeoyl-glucoside)

INCHI for CFc000282581 (Malvidin 3-caffeoyl-glucoside)

Structure for CFc000282581 (Malvidin 3-caffeoyl-glucoside)

3D Structure for CFc000282581 (Malvidin 3-caffeoyl-glucoside)