ChemFOnt: Showing chemical card for ent-Gallocatechin (CFc000336932)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:22 UTC

Chemfont ID

CFc000336932

Molecule Identification

Common Name

ent-Gallocatechin

Definition

Ent-gallocatechin, also known as (2s,3r)-flavan-3,3',4',5,5',7-hexol or (2s,3r)-gallocatechin, 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. Ent-gallocatechin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ent-gallocatechin can be found in common grape and tea, which makes ent-gallocatechin a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3R)-(-)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol	ChEBI
(2S,3R)-Flavan-3,3',4',5,5',7-hexol	ChEBI
(2S,3R)-Flavan-3,5,7,3',4',5'-hexol	ChEBI
(2S,3R)-Gallocatechin	ChEBI
ent-Gallocatechin	ChEBI

Chemical Formula

C₁₅H₁₄O₇

Average Molecular Weight

306.2675

Monoisotopic Molecular Weight

306.073952802

IUPAC Name

(2S,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

epigallocatechin

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@H]1C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m1/s1

InChI Key

XMOCLSLCDHWDHP-DOMZBBRYSA-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
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
Pyrogallol derivative
Benzenetriol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

gallocatechin (CHEBI:71225 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)
Quince (FooDB: FOOD00069)
Medlar (FooDB: FOOD00114)

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sweet cherry (FooDB: FOOD00145)

Tropical fruit

Berry

Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Strawberry (FooDB: FOOD00083)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Muscadine grape (FooDB: FOOD00203)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Citrus

Grapefruit (FooDB: FOOD00256)
Sweet orange (FooDB: FOOD00057)

Vegetable

Shoot vegetable

Globe artichoke (FooDB: FOOD00071)

Carrot (FooDB: FOOD00245)
Chicory (FooDB: FOOD00049)
Radish (FooDB: FOOD00153)

Mushroom

Common mushroom (FooDB: FOOD00547)

Onion-family vegetable

Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)

Tuber

Potato (FooDB: FOOD00175)

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Cereal and cereal product

Leavened bread

Wheat bread (FooDB: FOOD00808)

Cereal

Corn (FooDB: FOOD00205)
Rice (FooDB: FOOD00125)

Cereal product

Pasta (FooDB: FOOD00273)

Pulse

Bean

Common bean (FooDB: FOOD00134)
Broad bean (FooDB: FOOD00197)

Lentil

Lentils (FooDB: FOOD00098)

Pea

Chickpea (FooDB: FOOD00047)
Common pea (FooDB: FOOD00141)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Other beverage

Fruit-flavor drink (FooDB: FOOD00821)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Coffee and coffee product

Coffee

Gourd

Cocoa and cocoa product

Cocoa product

Hot chocolate (FooDB: FOOD00688)

Cocoa

Cocoa bean (FooDB: FOOD00182)

Confectionery

Candy

Other candy (FooDB: FOOD00679)

Tea

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.87 g/L	ALOGPS
logP	0.71	ALOGPS
logP	1.49	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.73	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	130.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.98 m³·mol⁻¹	ChemAxon
Polarizability	29.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon