ChemFOnt: Showing chemical card for Peonidin 3-galactoside (CFc000283166)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:11 UTC

Chemfont ID

CFc000283166

Molecule Identification

Common Name

Peonidin 3-galactoside

Definition

Peonidin 3-galactoside 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. Peonidin 3-galactoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Peonidin 3-galactoside can be found in a number of food items such as mango, red raspberry, rubus (blackberry, raspberry), and bilberry, which makes peonidin 3-galactoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₂H₂₃O₁₁

Average Molecular Weight

463.4114

Monoisotopic Molecular Weight

463.124036578

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

Traditional Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

CAS Registry Number

28148-89-2

SMILES

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

InChI Identifier

InChI=1S/C22H22O11/c1-30-15-4-9(2-3-12(15)25)21-16(7-11-13(26)5-10(24)6-14(11)31-21)32-22-20(29)19(28)18(27)17(8-23)33-22/h2-7,17-20,22-23,27-29H,8H2,1H3,(H2-,24,25,26)/p+1/t17-,18+,19+,20-,22-/m1/s1

InChI Key

ZZWPMFROUHHAKY-VRRLNDPFSA-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
3p-methoxyflavonoid-skeleton
7-hydroxyflavonoid
Hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Anthocyanidin
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
1-benzopyran
Benzopyran
Methoxybenzene
Phenoxy compound
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Oxane
Heteroaromatic compound
Secondary alcohol
Polyol
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Primary alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303650)

Food

Fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Blackcurrant (FooDB: FOOD00155)
Lingonberry (FooDB: FOOD00194)
Strawberry (FooDB: FOOD00083)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Red raspberry (FooDB: FOOD00162)
Black crowberry (FooDB: FOOD00075)
Black chokeberry (FooDB: FOOD00136)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Canada blueberry (FooDB: FOOD00211)
Summer grape (FooDB: FOOD00227)
Rabbiteye blueberry (FooDB: FOOD00898)

Tropical fruit

Mango (FooDB: FOOD00106)

Pome

Pear (FooDB: FOOD00152)

Drupe

Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.42 g/L	ALOGPS
logP	1.18	ALOGPS
logP	0.42	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	182.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.74 m³·mol⁻¹	ChemAxon
Polarizability	45.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0303650

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017307

KNApSAcK ID

Not Available

Chemspider ID

9628877

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11454027

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Peonidin 3-galactoside (CFc000283166)

MOL for CFc000283166 (Peonidin 3-galactoside)

3D MOL for CFc000283166 (Peonidin 3-galactoside)

3D SDF for CFc000283166 (Peonidin 3-galactoside)

3D-SDF for CFc000283166 (Peonidin 3-galactoside)

PDB for CFc000283166 (Peonidin 3-galactoside)

3D PDB for CFc000283166 (Peonidin 3-galactoside)

SMILES for CFc000283166 (Peonidin 3-galactoside)

INCHI for CFc000283166 (Peonidin 3-galactoside)

Structure for CFc000283166 (Peonidin 3-galactoside)

3D Structure for CFc000283166 (Peonidin 3-galactoside)