ChemFOnt: Showing chemical card for (Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate (CFc000281520)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:59 UTC

Chemfont ID

CFc000281520

Molecule Identification

Common Name

(Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate

Definition

(cyanidin 3-o-(3-o-acetyl-beta-glucoside) (kaempferol 3-o-(2-o-beta-glucosyl-beta-glucoside)-7-o-beta-glucosiduronic acid) malonate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). (cyanidin 3-o-(3-o-acetyl-beta-glucoside) (kaempferol 3-o-(2-o-beta-glucosyl-beta-glucoside)-7-o-beta-glucosiduronic acid) malonate can be found in chives, which makes (cyanidin 3-o-(3-o-acetyl-beta-glucoside) (kaempferol 3-o-(2-o-beta-glucosyl-beta-glucoside)-7-o-beta-glucosiduronic acid) malonate a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Cyanidin 3-O-(3-O-acetyl-b-glucoside) (kaempferol 3-O-(2-O-b-glucosyl-b-glucoside)-7-O-b-glucosiduronate) malonate	Generator
(Cyanidin 3-O-(3-O-acetyl-b-glucoside) (kaempferol 3-O-(2-O-b-glucosyl-b-glucoside)-7-O-b-glucosiduronic acid) malonic acid	Generator
(Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronate) malonate	Generator
(Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonic acid	Generator
(Cyanidin 3-O-(3-O-acetyl-β-glucoside) (kaempferol 3-O-(2-O-β-glucosyl-β-glucoside)-7-O-β-glucosiduronate) malonate	Generator
(Cyanidin 3-O-(3-O-acetyl-β-glucoside) (kaempferol 3-O-(2-O-β-glucosyl-β-glucoside)-7-O-β-glucosiduronic acid) malonic acid	Generator

Chemical Formula

C₅₈H₅₉O₃₇

Average Molecular Weight

1348.0669

Monoisotopic Molecular Weight

1347.273517902

IUPAC Name

3-{[(2S,3R,4S,5R,6S)-6-{[(3-{[(2S,3R,4S,5S,6R)-6-carboxy-2-[(3-{[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy]-4,5-dihydroxyoxan-3-yl]oxy}-3-oxopropanoyl)oxy]methyl}-4-(carboxyoxy)-3,5-dihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

Traditional Name

3-{[(2S,3R,4S,5R,6S)-6-{[(3-{[(2S,3R,4S,5S,6R)-6-carboxy-2-[(3-{[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl)oxy]-4,5-dihydroxyoxan-3-yl]oxy}-3-oxopropanoyl)oxy]methyl}-4-(carboxyoxy)-3,5-dihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

CAS Registry Number

289656-02-6

SMILES

OC[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H](CO)O[C@H]2OC2=C(OC3=CC(O[C@@H]4O[C@H]([C@@H](O)[C@H](O)[C@H]4OC(=O)CC(=O)OC[C@@H]4O[C@@H](OC5=C([O+]=C6C=C(O)C=C(O)C6=C5)C5=CC(O)=C(O)C=C5)[C@H](O)[C@@H](OC(O)=O)[C@@H]4O)C(O)=O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C58H58O37/c59-14-30-36(69)40(73)44(77)54(88-30)94-52-41(74)37(70)31(15-60)89-57(52)92-49-39(72)35-26(66)10-21(11-28(35)86-47(49)17-1-4-19(61)5-2-17)84-56-51(43(76)42(75)50(93-56)53(79)80)91-34(68)13-33(67)83-16-32-38(71)48(95-58(81)82)45(78)55(90-32)87-29-12-22-24(64)8-20(62)9-27(22)85-46(29)18-3-6-23(63)25(65)7-18/h1-12,30-32,36-38,40-45,48,50-52,54-57,59-60,69-71,73-78H,13-16H2,(H7-,61,62,63,64,65,66,72,79,80,81,82)/p+1/t30-,31-,32-,36+,37+,38+,40-,41-,42-,43-,44+,45+,48-,50+,51+,52+,54-,55+,56+,57-/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302004)

Food

Herb and spice

Herb

Chives (FooDB: FOOD00009)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.6 g/L	ALOGPS
logP	1.03	ALOGPS
logP	-2.8	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.69	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	33	ChemAxon
Hydrogen Donor Count	19	ChemAxon
Polar Surface Area	593.62 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	305.99 m³·mol⁻¹	ChemAxon
Polarizability	126.1 Å³	ChemAxon
Number of Rings	10	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

HMDB0302004

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001735

KNApSAcK ID

Not Available

Chemspider ID

30780095

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 (Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate (CFc000281520)

MOL for CFc000281520 ((Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate)

3D MOL for CFc000281520 ((Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate)

3D SDF for CFc000281520 ((Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate)

3D-SDF for CFc000281520 ((Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate)

PDB for CFc000281520 ((Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate)

3D PDB for CFc000281520 ((Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate)

SMILES for CFc000281520 ((Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate)

INCHI for CFc000281520 ((Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate)

Structure for CFc000281520 ((Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate)

3D Structure for CFc000281520 ((Cyanidin 3-O-(3-O-acetyl-beta-glucoside) (kaempferol 3-O-(2-O-beta-glucosyl-beta-glucoside)-7-O-beta-glucosiduronic acid) malonate)