ChemFOnt: Showing chemical card for Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside (CFc000281407)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:45 UTC

Chemfont ID

CFc000281407

Molecule Identification

Common Name

Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside

Definition

Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-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. Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside can be found in sweet potato, which makes cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₅₁H₅₃O₂₇

Average Molecular Weight

1097.9503

Monoisotopic Molecular Weight

1097.27742149

IUPAC Name

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

Traditional Name

CAS Registry Number

170717-21-2

SMILES

OC[C@H]1O[C@@H](OC2=C3C=C(O[C@H]4O[C@H](COC(=O)\C=C\C5=CC(O)=C(O)C=C5)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@H](COC(=O)\C=C\C5=CC(O)=C(O)C=C5)[C@@H](O)[C@H](O)[C@H]4O)C(=[O+]C3=CC(O)=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C51H52O27/c52-17-34-39(62)42(65)45(68)49(75-34)73-32-15-23(53)14-31-24(32)16-33(47(72-31)22-5-8-27(56)30(59)13-22)74-51-48(44(67)41(64)36(77-51)19-71-38(61)10-4-21-2-7-26(55)29(58)12-21)78-50-46(69)43(66)40(63)35(76-50)18-70-37(60)9-3-20-1-6-25(54)28(57)11-20/h1-16,34-36,39-46,48-52,62-69H,17-19H2,(H6-,53,54,55,56,57,58,59,60,61)/p+1/t34-,35-,36-,39-,40-,41-,42+,43+,44+,45-,46-,48-,49-,50+,51+/m1/s1

InChI Key

QROHSXUMSFREKB-GTGMSLJISA-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
Anthocyanidin-5-o-glycoside
Anthocyanin
Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Styrene
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Oxane
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Heteroaromatic compound
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Organic oxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301891)

Food

Vegetable

Tuber

Sweet potato (FooDB: FOOD00092)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	2.43	ALOGPS
logP	1.87	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.65	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	444.8 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	267.87 m³·mol⁻¹	ChemAxon
Polarizability	103.86 Å³	ChemAxon
Number of Rings	8	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

HMDB0301891

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001580

KNApSAcK ID

Not Available

Chemspider ID

30780062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102524409

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside (CFc000281407)

MOL for CFc000281407 (Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside)

3D MOL for CFc000281407 (Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside)

3D SDF for CFc000281407 (Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside)

3D-SDF for CFc000281407 (Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside)

PDB for CFc000281407 (Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside)

3D PDB for CFc000281407 (Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside)

SMILES for CFc000281407 (Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside)

INCHI for CFc000281407 (Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside)

Structure for CFc000281407 (Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside)

3D Structure for CFc000281407 (Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside)