ChemFOnt: Showing chemical card for Peonidin 3,5-diglucoside (CFc000281671)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:17 UTC

Chemfont ID

CFc000281671

Molecule Identification

Common Name

Peonidin 3,5-diglucoside

Definition

Peonidin 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 3,5-diglucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Peonidin 3,5-diglucoside can be found in chives, common grape, pineapple, and sea-buckthornberry, which makes peonidin 3,5-diglucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₈H₃₃O₁₆

Average Molecular Weight

625.552

Monoisotopic Molecular Weight

625.176860008

IUPAC Name

7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1λ⁴-chromen-1-ylium

Traditional Name

7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1λ⁴-chromen-1-ylium

CAS Registry Number

132-37-6

SMILES

COC1=C(O)C=CC(=C1)C1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C2C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=CC2=[O+]1

InChI Identifier

InChI=1S/C28H32O16/c1-39-16-4-10(2-3-13(16)32)26-17(42-28-25(38)23(36)21(34)19(9-30)44-28)7-12-14(40-26)5-11(31)6-15(12)41-27-24(37)22(35)20(33)18(8-29)43-27/h2-7,18-25,27-30,33-38H,8-9H2,1H3,(H-,31,32)/p+1/t18-,19-,20-,21-,22+,23+,24-,25-,27-,28-/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302155)

Food

Herb and spice

Herb

Chives (FooDB: FOOD00009)

Fruit

Tropical fruit

Pineapple (FooDB: FOOD00012)

Berry

Common grape (FooDB: FOOD00204)
Sea-buckthornberry (FooDB: FOOD00087)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.97 g/L	ALOGPS
logP	-0.08	ALOGPS
logP	-2.2	ChemAxon
logS	-2.8	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	10	ChemAxon
Polar Surface Area	261.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	152.88 m³·mol⁻¹	ChemAxon
Polarizability	60.27 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

HMDB0302155

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002754

KNApSAcK ID

Not Available

Chemspider ID

4589999

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5488811

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Peonidin 3,5-diglucoside (CFc000281671)

MOL for CFc000281671 (Peonidin 3,5-diglucoside)

3D MOL for CFc000281671 (Peonidin 3,5-diglucoside)

3D SDF for CFc000281671 (Peonidin 3,5-diglucoside)

3D-SDF for CFc000281671 (Peonidin 3,5-diglucoside)

PDB for CFc000281671 (Peonidin 3,5-diglucoside)

3D PDB for CFc000281671 (Peonidin 3,5-diglucoside)

SMILES for CFc000281671 (Peonidin 3,5-diglucoside)

INCHI for CFc000281671 (Peonidin 3,5-diglucoside)

Structure for CFc000281671 (Peonidin 3,5-diglucoside)

3D Structure for CFc000281671 (Peonidin 3,5-diglucoside)