ChemFOnt: Showing chemical card for Peonidin 3-(coumaroyl-rutinoside) 5-glucoside (CFc000336246)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:29:16 UTC

Chemfont ID

CFc000336246

Molecule Identification

Common Name

Peonidin 3-(coumaroyl-rutinoside) 5-glucoside

Definition

Peonidin, also known as 3,4',5,7-tetrahydroxy-3'-methoxyflavylium or peonidin cation, is a member of the class of compounds known as 3'-o-methylated flavonoids. 3'-o-methylated flavonoids are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. Thus, peonidin is considered to be a flavonoid lipid molecule. Peonidin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Peonidin can be found in a number of food items such as common bean, alcoholic beverages, french plantain, and sweet potato, which makes peonidin a potential biomarker for the consumption of these food products. Peonidin exists in all eukaryotes, ranging from yeast to humans. Like most anthocyanidins, it is pH sensitive, and changes from red to blue as pH rises because anthocyanidins are highly conjugated chromophores. When the pH is changed, the extent of the conjugation (of the double bonds) is altered, which alters the wavelength of light energy absorbed by the molecule (Natural anthocyanidins are most stable in a very low pH environment; at pH 8.0, most become colorless.) At pH 2.0, peonidin is cherry red; at 3.0 a strong yellowish pink; at 5.0 it is grape red-purple; and at 8.0 it becomes deep blue; unlike many anthocyanidins, however, it is stable at higher pH, and has been isolated as a blue colorant from the brilliant "Heavenly Blue" morning glory (Ipomoea tricolor Cav cv) .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4',5,7-Tetrahydroxy-3'-methoxyflavylium	ChEBI
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-benzopyrylium	ChEBI
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-benzopyrylium chloride	ChEBI
Peonidin cation	ChEBI
Peonidin(1+)	ChEBI

Chemical Formula

C₁₆H₁₃O₆

Average Molecular Weight

301.2708

Monoisotopic Molecular Weight

301.071213148

IUPAC Name

3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium

CAS Registry Number

134-01-0

SMILES

COC1=C(O)C=CC(=C1)C1=C(O)C=C2C(O)=CC(O)=CC2=[O+]1

InChI Identifier

InChI=1S/C16H12O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-7H,1H3,(H3-,17,18,19,20)/p+1

InChI Key

XFDQJKDGGOEYPI-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3'-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
Polyol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin cation (CHEBI:75314 )
Anthocyanidins (C08726 )
Anthocyanidins (LMPK12010006 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0005797)

Food

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	1.9	ALOGPS
logP	3.08	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.01	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	103.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.6 m³·mol⁻¹	ChemAxon
Polarizability	30.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017306

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-15052

BiGG ID

Not Available

Wikipedia Link

Peonidin

METLIN ID

Not Available

PubChem Compound

441773

PDB ID

Not Available

ChEBI ID

75314

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Peonidin 3-(coumaroyl-rutinoside) 5-glucoside (CFc000336246)

MOL for CFc000336246 (Peonidin 3-(coumaroyl-rutinoside) 5-glucoside)

3D MOL for CFc000336246 (Peonidin 3-(coumaroyl-rutinoside) 5-glucoside)

3D SDF for CFc000336246 (Peonidin 3-(coumaroyl-rutinoside) 5-glucoside)

3D-SDF for CFc000336246 (Peonidin 3-(coumaroyl-rutinoside) 5-glucoside)

PDB for CFc000336246 (Peonidin 3-(coumaroyl-rutinoside) 5-glucoside)

3D PDB for CFc000336246 (Peonidin 3-(coumaroyl-rutinoside) 5-glucoside)

SMILES for CFc000336246 (Peonidin 3-(coumaroyl-rutinoside) 5-glucoside)

INCHI for CFc000336246 (Peonidin 3-(coumaroyl-rutinoside) 5-glucoside)

Structure for CFc000336246 (Peonidin 3-(coumaroyl-rutinoside) 5-glucoside)

3D Structure for CFc000336246 (Peonidin 3-(coumaroyl-rutinoside) 5-glucoside)