ChemFOnt: Showing chemical card for Malvidin 3-(6''-p-caffeyglucoside) (CFc000281420)

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

CFc000281420

Molecule Identification

Common Name

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

Definition

Malvidin 3-(6''-p-caffeyglucoside) is a member of the class of compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. Anthocyanidin 3-o-6-p-coumaroyl glycosides 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. Malvidin 3-(6''-p-caffeyglucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Malvidin 3-(6''-p-caffeyglucoside) can be synthesized from cis-caffeic acid. Malvidin 3-(6''-p-caffeyglucoside) can also be synthesized into malvidin. Malvidin 3-(6''-p-caffeyglucoside) can be found in common grape, which makes malvidin 3-(6''-p-caffeyglucoside) a potential biomarker for the consumption of this food product. Malvidin 3-(6''-p-caffeyglucoside) may be a unique S.cerevisiae (yeast) metabolite.

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-{[(2S,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)-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}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1λ⁴-chromen-1-ylium

CAS Registry Number

129016-23-5

SMILES

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

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-KWNZYCHBSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Methoxybenzene
Anisole
Benzoyl
Aryl ketone
Phenoxy compound
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120285 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301904)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

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	13	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	64.98 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

HMDB0301904

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001594

KNApSAcK ID

Not Available

Chemspider ID

9414258

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

131452

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Malvidin 3-(6''-p-caffeyglucoside) (CFc000281420)

MOL for CFc000281420 (Malvidin 3-(6''-p-caffeyglucoside))

3D MOL for CFc000281420 (Malvidin 3-(6''-p-caffeyglucoside))

3D SDF for CFc000281420 (Malvidin 3-(6''-p-caffeyglucoside))

3D-SDF for CFc000281420 (Malvidin 3-(6''-p-caffeyglucoside))

PDB for CFc000281420 (Malvidin 3-(6''-p-caffeyglucoside))

3D PDB for CFc000281420 (Malvidin 3-(6''-p-caffeyglucoside))

SMILES for CFc000281420 (Malvidin 3-(6''-p-caffeyglucoside))

INCHI for CFc000281420 (Malvidin 3-(6''-p-caffeyglucoside))

Structure for CFc000281420 (Malvidin 3-(6''-p-caffeyglucoside))

3D Structure for CFc000281420 (Malvidin 3-(6''-p-caffeyglucoside))