ChemFOnt: Showing chemical card for Delphinidin 3-feruloylglucoside (CFc000281185)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:19 UTC

Chemfont ID

CFc000281185

Molecule Identification

Common Name

Delphinidin 3-feruloylglucoside

Definition

Delphinidin 3-feruloylglucoside 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. Delphinidin 3-feruloylglucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Delphinidin 3-feruloylglucoside can be found in common bean, green bean, and yellow wax bean, which makes delphinidin 3-feruloylglucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₁H₂₉O₁₅

Average Molecular Weight

641.553

Monoisotopic Molecular Weight

641.150645258

IUPAC Name

5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

CAS Registry Number

None

SMILES

[H][C@]1(COC(=O)\C=C\C2=CC(OC)=C(O)C=C2)O[C@@]([H])(OC2=C([O+]=C3C=C(O)C=C(O)C3=C2)C2=CC(O)=C(O)C(O)=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C31H28O15/c1-42-22-6-13(2-4-17(22)33)3-5-25(37)43-12-24-27(39)28(40)29(41)31(46-24)45-23-11-16-18(34)9-15(32)10-21(16)44-30(23)14-7-19(35)26(38)20(36)8-14/h2-11,24,27-29,31,39-41H,12H2,1H3,(H5-,32,33,34,35,36,37,38)/p+1/t24-,27-,28+,29-,31-/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301669)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.079 g/L	ALOGPS
logP	2.7	ALOGPS
logP	3.26	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	249.2 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	166.25 m³·mol⁻¹	ChemAxon
Polarizability	62.03 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

HMDB0301669

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000075

KNApSAcK ID

Not Available

Chemspider ID

Not Available

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 Delphinidin 3-feruloylglucoside (CFc000281185)

MOL for CFc000281185 (Delphinidin 3-feruloylglucoside)

3D MOL for CFc000281185 (Delphinidin 3-feruloylglucoside)

3D SDF for CFc000281185 (Delphinidin 3-feruloylglucoside)

3D-SDF for CFc000281185 (Delphinidin 3-feruloylglucoside)

PDB for CFc000281185 (Delphinidin 3-feruloylglucoside)

3D PDB for CFc000281185 (Delphinidin 3-feruloylglucoside)

SMILES for CFc000281185 (Delphinidin 3-feruloylglucoside)

INCHI for CFc000281185 (Delphinidin 3-feruloylglucoside)

Structure for CFc000281185 (Delphinidin 3-feruloylglucoside)

3D Structure for CFc000281185 (Delphinidin 3-feruloylglucoside)