ChemFOnt: Showing chemical card for Peonidin acetyl 3,5-diglucoside (CFc000281411)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:46 UTC

Chemfont ID

CFc000281411

Molecule Identification

Common Name

Peonidin acetyl 3,5-diglucoside

Definition

Peonidin acetyl 3,5-diglucoside is a member of the class of compounds known as anthocyanidin-5-o-glycosides. Anthocyanidin-5-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Peonidin acetyl 3,5-diglucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Peonidin acetyl 3,5-diglucoside can be found in common grape, which makes peonidin acetyl 3,5-diglucoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₀H₃₅O₁₇

Average Molecular Weight

667.5887

Monoisotopic Molecular Weight

667.187424694

IUPAC Name

3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-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

None

SMILES

COC1=C(O)C=CC(=C1)C1=[O+]C2=CC(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2C=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H34O17/c1-11(32)42-10-21-23(36)25(38)27(40)30(47-21)45-19-8-14-16(43-28(19)12-3-4-15(34)18(5-12)41-2)6-13(33)7-17(14)44-29-26(39)24(37)22(35)20(9-31)46-29/h3-8,20-27,29-31,35-40H,9-10H2,1-2H3,(H-,33,34)/p+1/t20-,21-,22-,23-,24+,25+,26-,27-,29-,30-/m1/s1

InChI Key

KOJLDSZARRTMAS-FYBHVKCMSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-5-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-5-o-glycoside
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Methoxyphenol
1-benzopyran
Benzopyran
Anisole
Methoxybenzene
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Polyol
Acetal
Ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Primary alcohol
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301895)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.69 g/L	ALOGPS
logP	0.64	ALOGPS
logP	-1.8	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.66	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	267.66 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	162.04 m³·mol⁻¹	ChemAxon
Polarizability	64.29 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001585

KNApSAcK ID

Not Available

Chemspider ID

Not Available

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 Peonidin acetyl 3,5-diglucoside (CFc000281411)

MOL for CFc000281411 (Peonidin acetyl 3,5-diglucoside)

3D MOL for CFc000281411 (Peonidin acetyl 3,5-diglucoside)

3D SDF for CFc000281411 (Peonidin acetyl 3,5-diglucoside)

3D-SDF for CFc000281411 (Peonidin acetyl 3,5-diglucoside)

PDB for CFc000281411 (Peonidin acetyl 3,5-diglucoside)

3D PDB for CFc000281411 (Peonidin acetyl 3,5-diglucoside)

SMILES for CFc000281411 (Peonidin acetyl 3,5-diglucoside)

INCHI for CFc000281411 (Peonidin acetyl 3,5-diglucoside)

Structure for CFc000281411 (Peonidin acetyl 3,5-diglucoside)

3D Structure for CFc000281411 (Peonidin acetyl 3,5-diglucoside)