ChemFOnt: Showing chemical card for Epigallocatechin 3-caffeate (CFc000281442)

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

CFc000281442

Molecule Identification

Common Name

Epigallocatechin 3-caffeate

Definition

Epigallocatechin 3-caffeate is a member of the class of compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety. Thus, epigallocatechin 3-caffeate is considered to be a flavonoid lipid molecule. Epigallocatechin 3-caffeate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Epigallocatechin 3-caffeate can be found in tea, which makes epigallocatechin 3-caffeate a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Epigallocatechin 3-O-caffeic acid	Generator
Epigallocatechin 3-caffeic acid	Generator

Chemical Formula

C₂₄H₂₀O₁₀

Average Molecular Weight

468.4096

Monoisotopic Molecular Weight

468.10564686

IUPAC Name

(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

epigallocatechin 3-O-caffeate

CAS Registry Number

122412-14-0

SMILES

OC1=CC2=C(C[C@@H](OC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1

InChI Identifier

InChI=1S/C24H20O10/c25-13-8-16(27)14-10-21(33-22(31)4-2-11-1-3-15(26)17(28)5-11)24(34-20(14)9-13)12-6-18(29)23(32)19(30)7-12/h1-9,21,24-30,32H,10H2/b4-2+/t21-,24-/m1/s1

InChI Key

BNLVODKLELGOBT-WEDYXYFPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Epigallocatechins

Alternative Parents

Substituents

Epigallocatechin
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Coumaric acid or derivatives
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Benzopyran
1-benzopyran
Chromane
Benzenetriol
Pyrogallol derivative
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020118 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301926)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	2.9	ALOGPS
logP	3.92	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.53	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.51 m³·mol⁻¹	ChemAxon
Polarizability	45.71 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0301926

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001634

KNApSAcK ID

C00008906

Chemspider ID

10252194

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14284598

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Epigallocatechin 3-caffeate (CFc000281442)

MOL for CFc000281442 (Epigallocatechin 3-caffeate)

3D MOL for CFc000281442 (Epigallocatechin 3-caffeate)

3D SDF for CFc000281442 (Epigallocatechin 3-caffeate)

3D-SDF for CFc000281442 (Epigallocatechin 3-caffeate)

PDB for CFc000281442 (Epigallocatechin 3-caffeate)

3D PDB for CFc000281442 (Epigallocatechin 3-caffeate)

SMILES for CFc000281442 (Epigallocatechin 3-caffeate)

INCHI for CFc000281442 (Epigallocatechin 3-caffeate)

Structure for CFc000281442 (Epigallocatechin 3-caffeate)

3D Structure for CFc000281442 (Epigallocatechin 3-caffeate)