ChemFOnt: Showing chemical card for Peonidin 3-(6''-caffeoyl-glucoside) (CFc000281410)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:46 UTC

Chemfont ID

CFc000281410

Molecule Identification

Common Name

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

Definition

Peonidin 3-(6''-caffeoyl-glucoside) 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. Peonidin 3-(6''-caffeoyl-glucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Peonidin 3-(6''-caffeoyl-glucoside) can be found in common grape, which makes peonidin 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

C₃₁H₂₉O₁₄

Average Molecular Weight

625.5536

Monoisotopic Molecular Weight

625.155730636

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-methoxyphenyl)-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-methoxyphenyl)-1λ⁴-chromen-1-ylium

CAS Registry Number

164584-53-6

SMILES

COC1=C(O)C=CC(=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C31H28O14/c1-41-23-9-15(4-6-19(23)34)30-24(12-17-20(35)10-16(32)11-22(17)43-30)44-31-29(40)28(39)27(38)25(45-31)13-42-26(37)7-3-14-2-5-18(33)21(36)8-14/h2-12,25,27-29,31,38-40H,13H2,1H3,(H4-,32,33,34,35,36,37)/p+1/t25-,27-,28+,29-,31-/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301894)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	3.27	ALOGPS
logP	3.55	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.39	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	228.97 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	164.27 m³·mol⁻¹	ChemAxon
Polarizability	62.11 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

HMDB0301894

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001584

KNApSAcK ID

Not Available

Chemspider ID

9562916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11388006

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Peonidin 3-(6''-caffeoyl-glucoside) (CFc000281410)

MOL for CFc000281410 (Peonidin 3-(6''-caffeoyl-glucoside))

3D MOL for CFc000281410 (Peonidin 3-(6''-caffeoyl-glucoside))

3D SDF for CFc000281410 (Peonidin 3-(6''-caffeoyl-glucoside))

3D-SDF for CFc000281410 (Peonidin 3-(6''-caffeoyl-glucoside))

PDB for CFc000281410 (Peonidin 3-(6''-caffeoyl-glucoside))

3D PDB for CFc000281410 (Peonidin 3-(6''-caffeoyl-glucoside))

SMILES for CFc000281410 (Peonidin 3-(6''-caffeoyl-glucoside))

INCHI for CFc000281410 (Peonidin 3-(6''-caffeoyl-glucoside))

Structure for CFc000281410 (Peonidin 3-(6''-caffeoyl-glucoside))

3D Structure for CFc000281410 (Peonidin 3-(6''-caffeoyl-glucoside))