ChemFOnt: Showing chemical card for Peonidin 3-feruloyl-diglucoside 5-glucoside (CFc000281413)

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

CFc000281413

Molecule Identification

Common Name

Peonidin 3-feruloyl-diglucoside 5-glucoside

Definition

Peonidin 3-feruloyl-diglucoside 5-glucoside is a member of the class of compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. Anthocyanidin 3-o-6-p-coumaroyl glycosides are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Peonidin 3-feruloyl-diglucoside 5-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Peonidin 3-feruloyl-diglucoside 5-glucoside can be found in sweet potato, which makes peonidin 3-feruloyl-diglucoside 5-glucoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₄H₅₁O₂₄

Average Molecular Weight

963.8613

Monoisotopic Molecular Weight

963.27702756

IUPAC Name

3-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-({[(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxy}methyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-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

144093-82-3

SMILES

COC1=C(O)C=C(\C=C\C(=O)OC[C@H]2O[C@@H](OC3=CC4=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C=C(O)C=C4[O+]=C3C3=CC(OC)=C(O)C=C3)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@@H]2O)C=C1

InChI Identifier

InChI=1S/C44H50O24/c1-59-23-7-3-17(9-22(23)49)4-8-31(50)61-16-30-34(53)37(56)41(68-43-39(58)36(55)33(52)29(15-46)66-43)44(67-30)64-27-13-20-24(62-40(27)18-5-6-21(48)26(10-18)60-2)11-19(47)12-25(20)63-42-38(57)35(54)32(51)28(14-45)65-42/h3-13,28-30,32-39,41-46,51-58H,14-16H2,1-2H3,(H2-,47,48,49)/p+1/b8-4+/t28-,29-,30-,32-,33-,34-,35+,36+,37+,38-,39-,41-,42-,43+,44-/m1/s1

InChI Key

UQSLQWFUWYJIMM-AEGWHFIMSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin 3-O-6-p-coumaroyl glycosides

Alternative Parents

Substituents

Anthocyanidin 3-o-6-p-coumaroyl-glycoside
Anthocyanin
Anthocyanidin-5-o-glycoside
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
7-hydroxyflavonoid
4'-hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
Cinnamic acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
O-glycosyl compound
Disaccharide
Glycosyl compound
Benzopyran
Methoxyphenol
1-benzopyran
Methoxybenzene
Styrene
Phenoxy compound
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxane
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Ether
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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: HMDB0301897)

Food

Vegetable

Tuber

Sweet potato (FooDB: FOOD00092)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	1.33	ALOGPS
logP	-1.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.66	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	376.27 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	233.31 m³·mol⁻¹	ChemAxon
Polarizability	94.09 Å³	ChemAxon
Number of Rings	7	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

HMDB0301897

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001587

KNApSAcK ID

Not Available

Chemspider ID

30780071

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157009777

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Peonidin 3-feruloyl-diglucoside 5-glucoside (CFc000281413)

MOL for CFc000281413 (Peonidin 3-feruloyl-diglucoside 5-glucoside)

3D MOL for CFc000281413 (Peonidin 3-feruloyl-diglucoside 5-glucoside)

3D SDF for CFc000281413 (Peonidin 3-feruloyl-diglucoside 5-glucoside)

3D-SDF for CFc000281413 (Peonidin 3-feruloyl-diglucoside 5-glucoside)

PDB for CFc000281413 (Peonidin 3-feruloyl-diglucoside 5-glucoside)

3D PDB for CFc000281413 (Peonidin 3-feruloyl-diglucoside 5-glucoside)

SMILES for CFc000281413 (Peonidin 3-feruloyl-diglucoside 5-glucoside)

INCHI for CFc000281413 (Peonidin 3-feruloyl-diglucoside 5-glucoside)

Structure for CFc000281413 (Peonidin 3-feruloyl-diglucoside 5-glucoside)

3D Structure for CFc000281413 (Peonidin 3-feruloyl-diglucoside 5-glucoside)