ChemFOnt: Showing chemical card for 5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside (CFc000281522)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:59 UTC

Chemfont ID

CFc000281522

Molecule Identification

Common Name

5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside

Definition

5-carboxypyranopelargonidin 3-o-beta-glucopyranoside is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 5-carboxypyranopelargonidin 3-o-beta-glucopyranoside can be found in strawberry, which makes 5-carboxypyranopelargonidin 3-o-beta-glucopyranoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Carboxypyranopelargonidin 3-O-b-glucopyranoside	Generator
5-Carboxypyranopelargonidin 3-O-β-glucopyranoside	Generator

Chemical Formula

C₂₄H₂₁O₁₂

Average Molecular Weight

501.4163

Monoisotopic Molecular Weight

501.103301136

IUPAC Name

7-carboxy-11-hydroxy-3-(4-hydroxyphenyl)-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium

Traditional Name

7-carboxy-11-hydroxy-3-(4-hydroxyphenyl)-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium

CAS Registry Number

680227-23-0

SMILES

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

InChI Identifier

InChI=1S/C24H20O12/c25-8-16-18(28)19(29)20(30)24(35-16)36-22-12-7-15(23(31)32)33-13-5-11(27)6-14(17(12)13)34-21(22)9-1-3-10(26)4-2-9/h1-7,16,18-20,24-25,28-30H,8H2,(H2-,26,27,31,32)/p+1/t16-,18-,19+,20-,24+/m1/s1

InChI Key

AXDSYHMPWOHFSW-KXJGTOPRSA-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
7-hydroxyflavonoid
4'-hydroxyflavonoid
Anthocyanidin
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302006)

Food

Fruit

Berry

Strawberry (FooDB: FOOD00083)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	1.93	ALOGPS
logP	0.89	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.27	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	199.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	129.47 m³·mol⁻¹	ChemAxon
Polarizability	47.76 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	No	ChemAxon

External Links

HMDB ID

HMDB0302006

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001737

KNApSAcK ID

Not Available

Chemspider ID

4482034

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-Carboxypyranopelargonidin 3-O-beta-glucopyranoside (CFc000281522)

MOL for CFc000281522 (5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside)

3D MOL for CFc000281522 (5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside)

3D SDF for CFc000281522 (5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside)

3D-SDF for CFc000281522 (5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside)

PDB for CFc000281522 (5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside)

3D PDB for CFc000281522 (5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside)

SMILES for CFc000281522 (5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside)

INCHI for CFc000281522 (5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside)

Structure for CFc000281522 (5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside)

3D Structure for CFc000281522 (5-Carboxypyranopelargonidin 3-O-beta-glucopyranoside)