Showing Compound Epicatechin 3-gallate (FDB017114)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:51 UTC

Update date

2019-11-26 03:14:13 UTC

Primary ID

FDB017114

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Epicatechin 3-gallate

Description

(-)-Epicatechin 3-O-gallate, also known as 3-O-galloylepicatechin or ECG, belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin (-)-Epicatechin 3-O-gallate is a bitter tasting compound (-)-Epicatechin 3-O-gallate is found, on average, in the highest concentration within a few different foods, such as red tea, herbal tea, and green tea and in a lower concentration in peppermints (Mentha X piperita), common grapes (Vitis vinifera), and medlars (Mespilus germanica) (-)-Epicatechin 3-O-gallate has also been detected, but not quantified in, several different foods, such as kiwis (Actinidia chinensis), rubus (blackberry, raspberry), sweet oranges (Citrus sinensis), common wheats (Triticum aestivum), and pistachios (Pistacia vera). This could make (-)-epicatechin 3-O-gallate a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on (-)-Epicatechin 3-O-gallate.

CAS Number

1257-08-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallate	ChEBI
3-Gallate(-)-epicatechol	ChEBI
3-O-Galloylepicatechin	ChEBI
ECG	ChEBI
Teatannin	ChEBI
(-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallic acid	Generator
3-Gallic acid(-)-epicatechol	Generator
(-)-Epicatechin 3-O-gallic acid	Generator
(-)-Epicatechin gallate	HMDB
(-)-Epicatechin-3-gallate	HMDB
(-)-Epicatechin-3-O-gallate	HMDB
Epicatechin gallate	HMDB, MeSH
Epicatechin gallate, (2R-cis)-isomer	HMDB, MeSH
Epicatechol, gallate	HMDB
L-Epicatechin gallate	HMDB
Epicatechin-3-O-gallate	MeSH, HMDB
Epicatechin-3-gallate	MeSH, HMDB
Epicatechin-3-galloyl ester	MeSH, HMDB
Epicatechin 3-gallic acid	Generator
(-)-Epicatechin 3-gallate	manual
(-)-Epicatechin 3-O-gallate	manual
Epicatechin 3-gallate	manual
Epicatechol, 3-gallate, (-)-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	2.55	ALOGPS
logP	3.38	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.03	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	4	ChemAxon
Refractivity	109.76 m³·mol⁻¹	ChemAxon
Polarizability	41.64 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

Chemical Formula

C22H18O10

IUPAC name

(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

InChI Identifier

InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1

InChI Key

LSHVYAFMTMFKBA-TZIWHRDSSA-N

Isomeric SMILES

OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1

Average Molecular Weight

442.376

Monoisotopic Molecular Weight

442.08999678

Classification

Description

Belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechin gallates

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:70255 )
gallate ester (CHEBI:70255 )
catechin (CHEBI:70255 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020090 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biofluid and excreta:

Blood

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 59.73%; H 4.10%; O 36.17%	DFC
Melting Point	Mp 257-258° (253°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]23D -160.6 (c, 0.22 in Me2CO)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Epicatechin 3-gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0umi-0920000000-718b2102383cc9dc533e	Spectrum
Predicted GC-MS	Epicatechin 3-gallate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004l-1490224000-de77e2646c7aba3a8def	Spectrum
Predicted GC-MS	Epicatechin 3-gallate, TBDMS_3_23, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epicatechin 3-gallate, TBDMS_4_19, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epicatechin 3-gallate, TBDMS_4_25, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epicatechin 3-gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epicatechin 3-gallate, "(-)-Epicatechin 3-O-gallate,3TBDMS,#23" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0292000000-ece704ccdb047a088d28	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0292000000-d89b96c676e7c3398d8f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0170-0950000000-685c095616785cc82303	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-014i-0940200000-84b58b678cc59833a025	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0290000000-440ff7c7a589e1c058b5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0290000000-8f606522637d9033c95f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0002-0098500000-0c0b2ca06b9e49aa356b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0002-0097500000-7a41879feecb968154e9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0029600000-77ceea44aa3ce7f822f9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0029600000-7f271696d73430ee7463	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0900000000-21da01e01ba7fa12d6cb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-0900000000-1b53eabb63f51dd0886f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-e435428b44afb21a7eee	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0900000000-a3b08dd3f89619c2d4f3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0930000000-19d10b8c4fe8d2256c14	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014u-0960500000-6417fae4919951138986	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0940000000-ce6989df78eb09b24d1f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-cff394f106b307da1857	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0920400000-e7005e91544f51f7efe1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-0910000000-a428a4e56e1884d5b86a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-2900000000-d86fe441a677946b2205	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0310900000-98e9c41598a749627127	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gdl-0913300000-af1ea1d6588fca8f1f9f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-0900000000-60192713dbf412058de2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0130900000-406473c14c03e2f28625	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

97034

ChEMBL ID

CHEMBL36327

KEGG Compound ID

Not Available

Pubchem Compound ID

107905

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

128

DrugBank ID

Not Available

HMDB ID

HMDB37944

CRC / DFC (Dictionary of Food Compounds) ID

CML31-M:KWF59-Y

EAFUS ID

Not Available

Dr. Duke ID

BIGG ID

Not Available

KNApSAcK ID

C00008866

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

128

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
angiotensin converting enzyme inhibitor	35457	An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).	DUKE
acetyl-CoA-carboxylase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
anti cariogenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hepatotoxic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti mutagenic			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti peroxidant			DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
catechol O-methyltransferase inhibitor	48406	An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6).	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
glucosyl-transferase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
immunostimulant	50847	A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.	DUKE
lipoxygenase inhibitor	35856	A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.	DUKE
methyl-guanidine inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
mitogen	52290	A chemical substance that encourages a cell to commence cell division, triggering mitosis.	DUKE
nephroprotective	76595	Any protective agent that is able to prevent damage to the kidney.	DUKE
xanthine oxidase inhibitor	35634	An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).	DUKE
alpha-amylase inhibitor	50627	An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-amylase (EC 3.2.1.1).	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).