ChemFOnt: Showing chemical card for Catechin-(4alpha->8)-epicatechin 3'-gallate (CFc000281446)

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

CFc000281446

Molecule Identification

Common Name

Catechin-(4alpha->8)-epicatechin 3'-gallate

Definition

Catechin-(4alpha->8)-epicatechin 3'-gallate, also known as (-)-epicatechin-(4a->8)-(+)-catechin-3'-O-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''. Catechin-(4alpha->8)-epicatechin 3'-gallate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Catechin-(4alpha->8)-epicatechin 3'-gallate can be synthesized from gallic acid. Catechin-(4alpha->8)-epicatechin 3'-gallate can also be synthesized into procyanidin B4. Catechin-(4alpha->8)-epicatechin 3'-gallate can be found in common grape and tea, which makes catechin-(4alpha->8)-epicatechin 3'-gallate a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Epicatechin-(4alpha->8)-(+)-catechin-3'-O-gallate	ChEBI
(-)-Epicatechin-(4a->8)-(+)-catechin-3'-O-gallate	Generator
(-)-Epicatechin-(4a->8)-(+)-catechin-3'-O-gallic acid	Generator
(-)-Epicatechin-(4alpha->8)-(+)-catechin-3'-O-gallic acid	Generator
(-)-Epicatechin-(4α->8)-(+)-catechin-3'-O-gallate	Generator
(-)-Epicatechin-(4α->8)-(+)-catechin-3'-O-gallic acid	Generator
Procyanidin b4 3'-O-gallic acid	Generator
Catechin-(4a->8)-epicatechin 3'-gallate	Generator
Catechin-(4a->8)-epicatechin 3'-gallic acid	Generator
Catechin-(4alpha->8)-epicatechin 3'-gallic acid	Generator
Catechin-(4α->8)-epicatechin 3'-gallate	Generator
Catechin-(4α->8)-epicatechin 3'-gallic acid	Generator

Chemical Formula

C₃₇H₃₀O₁₆

Average Molecular Weight

730.6245

Monoisotopic Molecular Weight

730.153384912

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-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

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-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

CAS Registry Number

89064-33-5

SMILES

O[C@@H]1[C@H](OC2=C([C@H]1C1=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)C(O)=CC(O)=C2)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C37H30O16/c38-16-9-23(44)29-27(10-16)51-35(14-2-4-19(40)22(43)6-14)33(49)31(29)30-24(45)12-20(41)17-11-28(52-37(50)15-7-25(46)32(48)26(47)8-15)34(53-36(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,28,31,33-35,38-49H,11H2/t28-,31+,33+,34-,35-/m1/s1

InChI Key

VLFKNLZNDSEVBZ-GUFPFSRMSA-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:75655 )
gallate ester (CHEBI:75655 )
proanthocyanidin (CHEBI:75655 )
biflavonoid (CHEBI:75655 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301930)

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.074 g/L	ALOGPS
logP	3.32	ALOGPS
logP	4.7	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.03	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	287.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	182.27 m³·mol⁻¹	ChemAxon
Polarizability	69.79 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

HMDB0301930

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001638

KNApSAcK ID

Not Available

Chemspider ID

30785667

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

75655

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Catechin-(4alpha->8)-epicatechin 3'-gallate (CFc000281446)

MOL for CFc000281446 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

3D MOL for CFc000281446 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

3D SDF for CFc000281446 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

3D-SDF for CFc000281446 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

PDB for CFc000281446 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

3D PDB for CFc000281446 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

SMILES for CFc000281446 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

INCHI for CFc000281446 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

Structure for CFc000281446 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

3D Structure for CFc000281446 (Catechin-(4alpha->8)-epicatechin 3'-gallate)