ContaminantDB: Epicatechin 3-gallate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 02:35:48 UTC

Update Date

2016-11-09 01:19:15 UTC

Accession Number

CHEM031366

Identification

Common Name

Epicatechin 3-gallate

Class

Small Molecule

Description

A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₂₂H₁₈O₁₀

Average Molecular Mass

442.376 g/mol

Monoisotopic Mass

442.090 g/mol

CAS Registry Number

1257-08-5

IUPAC Name

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

Traditional Name

(-)-epicatechin 3-O-gallate

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

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

Chemical Taxonomy

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0umi-0920000000-718b2102383cc9dc533e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-004l-1490224000-de77e2646c7aba3a8def	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_23) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_19) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_25) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("(-)-Epicatechin 3-O-gallate,3TBDMS,#23" TMS) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0292000000-ece704ccdb047a088d28	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0292000000-d89b96c676e7c3398d8f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0170-0950000000-685c095616785cc82303	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-014i-0940200000-84b58b678cc59833a025	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0290000000-440ff7c7a589e1c058b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0290000000-8f606522637d9033c95f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0002-0098500000-0c0b2ca06b9e49aa356b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0002-0097500000-7a41879feecb968154e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0029600000-77ceea44aa3ce7f822f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0029600000-7f271696d73430ee7463	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0900000000-21da01e01ba7fa12d6cb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-0900000000-1b53eabb63f51dd0886f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-e435428b44afb21a7eee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0900000000-a3b08dd3f89619c2d4f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0930000000-19d10b8c4fe8d2256c14	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014u-0960500000-6417fae4919951138986	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0940000000-ce6989df78eb09b24d1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-cff394f106b307da1857	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-0920400000-e7005e91544f51f7efe1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-0910000000-a428a4e56e1884d5b86a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-2900000000-d86fe441a677946b2205	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0310900000-98e9c41598a749627127	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gdl-0913300000-af1ea1d6588fca8f1f9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-0900000000-60192713dbf412058de2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0130900000-406473c14c03e2f28625	Spectrum