ChemFOnt: Showing chemical card for 5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside) (CFc000281466)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:52 UTC

Chemfont ID

CFc000281466

Molecule Identification

Common Name

5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside)

Definition

5-carboxypyranocyanidin 3-o-(6''-o-malonyl-beta-glucopyranoside) is a member of the class of compounds known as anthocyanidin-3-o-glycosides. Anthocyanidin-3-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. 5-carboxypyranocyanidin 3-o-(6''-o-malonyl-beta-glucopyranoside) is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 5-carboxypyranocyanidin 3-o-(6''-o-malonyl-beta-glucopyranoside) can be found in garden onion, which makes 5-carboxypyranocyanidin 3-o-(6''-o-malonyl-beta-glucopyranoside) a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-b-glucopyranoside)	Generator
5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-β-glucopyranoside)	Generator

Chemical Formula

C₂₇H₂₃O₁₆

Average Molecular Weight

603.4619

Monoisotopic Molecular Weight

603.098609688

IUPAC Name

7-carboxy-4-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-3-(3,4-dihydroxyphenyl)-11-hydroxy-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium

Traditional Name

CAS Registry Number

566942-53-8

SMILES

O[C@@H]1[C@@H](COC(=O)CC(O)=O)O[C@@H](OC2=C3C=C(OC4=CC(O)=CC([O+]=C2C2=CC(O)=C(O)C=C2)=C34)C(O)=O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H22O16/c28-10-4-14-20-11(6-16(40-14)26(37)38)25(24(41-15(20)5-10)9-1-2-12(29)13(30)3-9)43-27-23(36)22(35)21(34)17(42-27)8-39-19(33)7-18(31)32/h1-6,17,21-23,27,34-36H,7-8H2,(H4-,28,29,30,31,32,37,38)/p+1/t17-,21-,22+,23-,27+/m1/s1

InChI Key

QYGZGEVHEDPHDA-VFTFQOQOSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-3-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Tricarboxylic acid or derivatives
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Oxane
Monocyclic benzene moiety
Benzenoid
1,3-dicarbonyl compound
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Oxacycle
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301950)

Food

Vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.34 g/L	ALOGPS
logP	2.21	ALOGPS
logP	0.9	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.16	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	263.11 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	146.94 m³·mol⁻¹	ChemAxon
Polarizability	55.38 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

HMDB0301950

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001663

KNApSAcK ID

Not Available

Chemspider ID

10190893

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 5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside) (CFc000281466)

MOL for CFc000281466 (5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D MOL for CFc000281466 (5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D SDF for CFc000281466 (5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D-SDF for CFc000281466 (5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

PDB for CFc000281466 (5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D PDB for CFc000281466 (5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

SMILES for CFc000281466 (5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

INCHI for CFc000281466 (5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

Structure for CFc000281466 (5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D Structure for CFc000281466 (5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))