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

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 agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.	DUKE
Acetyl-CoA-carboxylase inhibitor	23924	An agent that blocks the activity of acetyl-CoA-carboxylase, a key enzyme in fatty acid synthesis, reducing lipid production. Therapeutically, it is used to manage obesity, hyperlipidemia, and type 2 diabetes by decreasing fat storage and improving insulin sensitivity.	DUKE
Anti cariogenic	52217	An agent that prevents tooth decay, reducing bacterial acid production and plaque formation. Its biological role is to inhibit the growth of cariogenic bacteria, and its therapeutic applications include preventing dental caries and managing tooth decay. Key medical uses include toothpaste, mouthwashes, and dental varnishes to maintain oral health.	DUKE
Anti hepatotoxic	62868	An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.	DUKE
Anti HIV	22587	An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.	DUKE
Anti-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti peroxidant		An agent that prevents oxygen atom and peroxide formation, reducing oxidative stress and cell damage. It plays a biological role in protecting cells from free radicals. Therapeutically, it's used to manage conditions like cancer, Alzheimer's, and atherosclerosis, with key medical applications in neuroprotection, cardiovascular health, and anti-aging.	DUKE
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Catechol O-methyltransferase inhibitor	48406	An agent that blocks the activity of catechol O-methyltransferase, an enzyme involved in breaking down catecholamines. Therapeutically, it increases dopamine levels, commonly used in managing Parkinson's disease, depression, and anxiety disorders, as well as treating pain and fibromyalgia.	DUKE
Cytotoxic	52209	An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.	DUKE
Glucosyl-transferase inhibitor	23924	An agent that blocks the activity of glucosyl-transferase enzymes, preventing glycoprotein and glycolipid synthesis. It has therapeutic applications in cancer, infectious diseases, and inflammatory disorders, with key medical uses including anti-tumor, anti-viral, and anti-inflammatory treatments.	DUKE
Immunostimulant	50847	An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.	DUKE
Lipoxygenase inhibitor	35856	An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.	DUKE
Methyl-guanidine inhibitor	35222	An agent that blocks the activity of inducible nitric oxide synthase (iNOS), reducing nitric oxide production. Therapeutically, it has anti-inflammatory and neuroprotective effects, commonly used in managing conditions such as arthritis, sepsis, and neurodegenerative diseases.	DUKE
Mitogen	52290	A substance that induces cell division and proliferation, playing a key role in growth and development. Therapeutically, mitogens are used to stimulate tissue repair and regeneration. Medical applications include wound healing, tissue engineering, and cancer treatment, where mitogens can enhance chemotherapy efficacy or support hematopoiesis.	DUKE
Nephroprotective	76595	An agent that protects the kidneys from damage, reducing inflammation and oxidative stress. Therapeutically, it helps prevent or treat kidney diseases, such as nephropathy and acute kidney injury, and is used in managing conditions like diabetes and hypertension to preserve renal function.	DUKE
Xanthine oxidase inhibitor	35634	An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.	DUKE
Alpha-amylase inhibitor	50627	An agent that blocks the activity of alpha-amylase, an enzyme that breaks down carbohydrates. It reduces carbohydrate digestion and absorption, commonly used in managing diabetes, obesity, and weight loss, with potential therapeutic applications in glycemic control and metabolic disorders.	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).