ChemFOnt: Showing chemical card for Delphinidin 3-caffeoylglucoside (CFc000281415)

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

CFc000281415

Molecule Identification

Common Name

Delphinidin 3-caffeoylglucoside

Definition

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₀H₂₇O₁₅

Average Molecular Weight

627.5264

Monoisotopic Molecular Weight

627.134995194

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-(3,4,5-trihydroxyphenyl)-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-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C30H26O15/c31-14-8-17(33)15-10-22(29(43-21(15)9-14)13-6-19(35)25(38)20(36)7-13)44-30-28(41)27(40)26(39)23(45-30)11-42-24(37)4-2-12-1-3-16(32)18(34)5-12/h1-10,23,26-28,30,39-41H,11H2,(H6-,31,32,33,34,35,36,37,38)/p+1/t23-,26-,27+,28-,30-/m1/s1

InChI Key

CPESTIBYQUOXSA-LHRGPQAGSA-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
Hydroxyflavonoid
3'-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
1-benzopyran
Benzopyran
Pyrogallol derivative
Benzenetriol
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
Phenol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
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
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin glycoside (CHEBI:80474 )
Anthocyanidins (C16367 )
Anthocyanidins and anthocyanins (C16367 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301899)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	2.85	ALOGPS
logP	3.23	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	260.2 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	161.77 m³·mol⁻¹	ChemAxon
Polarizability	61.07 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

HMDB0301899

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

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 Delphinidin 3-caffeoylglucoside (CFc000281415)

MOL for CFc000281415 (Delphinidin 3-caffeoylglucoside)

3D MOL for CFc000281415 (Delphinidin 3-caffeoylglucoside)

3D SDF for CFc000281415 (Delphinidin 3-caffeoylglucoside)

3D-SDF for CFc000281415 (Delphinidin 3-caffeoylglucoside)

PDB for CFc000281415 (Delphinidin 3-caffeoylglucoside)

3D PDB for CFc000281415 (Delphinidin 3-caffeoylglucoside)

SMILES for CFc000281415 (Delphinidin 3-caffeoylglucoside)

INCHI for CFc000281415 (Delphinidin 3-caffeoylglucoside)

Structure for CFc000281415 (Delphinidin 3-caffeoylglucoside)

3D Structure for CFc000281415 (Delphinidin 3-caffeoylglucoside)