ChemFOnt: Showing chemical card for [Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate (CFc000281449)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:50 UTC

Chemfont ID

CFc000281449

Molecule Identification

Common Name

[Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate

Definition

[epicatechin-(4beta->8)]2-epicatechin 3'''-gallate is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. [epicatechin-(4beta->8)]2-epicatechin 3'''-gallate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). [epicatechin-(4beta->8)]2-epicatechin 3'''-gallate can be found in common grape, which makes [epicatechin-(4beta->8)]2-epicatechin 3'''-gallate a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3R)-2-(3,4-Dihydroxyphenyl)-8-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acid	Generator
[Epicatechin-(4b->8)]2-epicatechin 3'''-gallate	Generator
[Epicatechin-(4b->8)]2-epicatechin 3'''-gallic acid	Generator
[Epicatechin-(4beta->8)]2-epicatechin 3'''-gallic acid	Generator
[Epicatechin-(4β->8)]2-epicatechin 3'''-gallate	Generator
[Epicatechin-(4β->8)]2-epicatechin 3'''-gallic acid	Generator

Chemical Formula

C₅₂H₄₂O₂₂

Average Molecular Weight

1018.8767

Monoisotopic Molecular Weight

1018.216773028

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

490-46-0

SMILES

O[C@H]1[C@H](OC2=C([C@@H]1C1=C(O)C=C(O)C3=C1O[C@@H]([C@H](O)[C@H]3C1=C(O)C=C(O)C3=C1O[C@@H]([C@@H](C3)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C1=CC(O)=C(O)C=C1)C(O)=CC(O)=C2)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C52H42O22/c53-21-12-30(61)38-36(13-21)71-48(18-2-5-24(55)28(59)8-18)45(68)42(38)40-32(63)16-33(64)41-43(46(69)49(74-51(40)41)19-3-6-25(56)29(60)9-19)39-31(62)15-26(57)22-14-37(72-52(70)20-10-34(65)44(67)35(66)11-20)47(73-50(22)39)17-1-4-23(54)27(58)7-17/h1-13,15-16,37,42-43,45-49,53-69H,14H2/t37-,42-,43+,45-,46-,47-,48-,49-/m1/s1

InChI Key

FYNOPTDFZIWSDG-SRPXDWQMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

C-type proanthocyanidin
B-type proanthocyanidin
Proanthocyanidin
Bi- and polyflavonoid skeleton
Catechin gallate
Catechin
Hydroxyflavonoid
Flavan-3-ol
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
Benzoate ester
Chromane
Benzopyran
1-benzopyran
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Benzoyl
Catechol
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301933)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	3.86	ALOGPS
logP	6.02	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.03	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	17	ChemAxon
Polar Surface Area	397.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	254.78 m³·mol⁻¹	ChemAxon
Polarizability	96.41 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

HMDB0301933

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001641

KNApSAcK ID

Not Available

Chemspider ID

17297718

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16141214

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for [Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate (CFc000281449)

MOL for CFc000281449 ([Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate)

3D MOL for CFc000281449 ([Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate)

3D SDF for CFc000281449 ([Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate)

3D-SDF for CFc000281449 ([Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate)

PDB for CFc000281449 ([Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate)

3D PDB for CFc000281449 ([Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate)

SMILES for CFc000281449 ([Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate)

INCHI for CFc000281449 ([Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate)

Structure for CFc000281449 ([Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate)

3D Structure for CFc000281449 ([Epicatechin-(4beta->8)]2-epicatechin 3'''-gallate)