ChemFOnt: Showing chemical card for Pelargonidin 3,5-di-O-glucoside (CFc000282420)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:45 UTC

Chemfont ID

CFc000282420

Molecule Identification

Common Name

Pelargonidin 3,5-di-O-glucoside

Definition

Pelargonin 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. Pelargonin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Pelargonin can be found in a number of food items such as green bean, grass pea, pomegranate, and yellow wax bean, which makes pelargonin a potential biomarker for the consumption of these food products. Pelargonin is an anthocyanin. It is the 3,5-O-diglucoside of pelargonidin .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Monardin	HMDB
Pelargonidin 3,5-di-beta-D-glucopyranoside	HMDB
Pelargonidin 3,5-di-beta-D-glucoside	HMDB
Pelargonidin 3,5-diglucoside	HMDB
Pelargonidin 3,5-O-diglucoside	HMDB
Pelargonin?	HMDB
Punicin	HMDB
Salvinin?	HMDB

Chemical Formula

C₂₇H₃₁O₁₅

Average Molecular Weight

595.526

Monoisotopic Molecular Weight

595.166295322

IUPAC Name

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

Traditional Name

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

CAS Registry Number

17334-58-6

SMILES

OCC1OC(OC2=CC(O)=CC3=C2C=C(OC2OC(CO)C(O)C(O)C2O)C(=[O+]3)C2=CC=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C27H30O15/c28-8-17-19(32)21(34)23(36)26(41-17)39-15-6-12(31)5-14-13(15)7-16(25(38-14)10-1-3-11(30)4-2-10)40-27-24(37)22(35)20(33)18(9-29)42-27/h1-7,17-24,26-29,32-37H,8-9H2,(H-,30,31)/p+1

InChI Key

SLCKJKWFULXZBD-UHFFFAOYSA-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
4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0302904)
Extracellular (HMDB: HMDB0302904)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0302904)

Source

Exogenous

Exogenous (HMDB: HMDB0302904)

Food

Food (HMDB: HMDB0302904)

Fruit

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Endogenous

Plant

Plant (HMDB: HMDB0302904)
Fabaceae (HMDB: HMDB0302904)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0302904)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.2 g/L	ALOGPS
logP	-0.03	ALOGPS
logP	-2	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.66	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	252.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.42 m³·mol⁻¹	ChemAxon
Polarizability	57.23 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