ChemFOnt: Showing chemical card for Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside (CFc000281421)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:47 UTC

Chemfont ID

CFc000281421

Molecule Identification

Common Name

Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside

Definition

Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified 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. Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside can be found in hyssop, which makes malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₄H₄₅O₂₅

Average Molecular Weight

973.8131

Monoisotopic Molecular Weight

973.22499199

IUPAC Name

5-{[(2S,3R,4R,5S,6R)-5-[(2-carboxyacetyl)oxy]-6-{[(2-carboxyacetyl)oxy]methyl}-3,4-dihydroxyoxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

Traditional Name

CAS Registry Number

144940-57-8

SMILES

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

InChI Identifier

InChI=1S/C44H44O25/c1-60-25-9-19(10-26(61-2)35(25)54)41-27(66-43-39(58)37(56)36(55)28(67-43)16-62-32(51)8-5-18-3-6-20(45)7-4-18)13-22-23(64-41)11-21(46)12-24(22)65-44-40(59)38(57)42(69-34(53)15-31(49)50)29(68-44)17-63-33(52)14-30(47)48/h3-13,28-29,36-40,42-44,55-59H,14-17H2,1-2H3,(H4-,45,46,47,48,49,50,51,54)/p+1/t28-,29-,36-,37+,38-,39-,40-,42-,43-,44-/m1/s1

InChI Key

WLRHEJRFVKWTOH-OUOHEMENSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified 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

Flavonoid 3-O-p-coumaroyl glycosides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301905)

Food

Herb and spice

Herb

Hyssop (FooDB: FOOD00089)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.57	ALOGPS
logP	1.49	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	2.94	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	231.89 m³·mol⁻¹	ChemAxon
Polarizability	91.7 Å³	ChemAxon
Number of Rings	6	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

HMDB0301905

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001595

KNApSAcK ID

Not Available

Chemspider ID

30780077

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101633887

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside (CFc000281421)

MOL for CFc000281421 (Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside)

3D MOL for CFc000281421 (Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside)

3D SDF for CFc000281421 (Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside)

3D-SDF for CFc000281421 (Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside)

PDB for CFc000281421 (Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside)

3D PDB for CFc000281421 (Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside)

SMILES for CFc000281421 (Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside)

INCHI for CFc000281421 (Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside)

Structure for CFc000281421 (Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside)

3D Structure for CFc000281421 (Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside)