Identification

PhytoHub ID
PHUB000263
Name
(-)-Epicatechin 3-O-gallate
Systematic Name
Not Available
Synonyms
Not Available
CAS Number
Not Available
Average Mass
442.376
Monoisotopic Mass
442.08999678
Chemical Formula
C22H18O10
IUPAC Name
epicatechin gallate
InChI Key
LSHVYAFMTMFKBA-TZIWHRDSSA-N
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
SMILES
OC1=CC(O)=C2C[[email protected]@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[[email protected]](OC2=C1)C1=CC(O)=C(O)C=C1
Structure

Calculated Properties

Solubility (ALOGPS)
4.43e-02 g/l
LogS (ALOGPS)
-4.00
LogP (ALOGPS)
2.55
Hydrogen Acceptors
9
Hydrogen Donors
7
Rotatable Bond Count
4
Polar Surface Area
177.14
Refractivity
109.76439999999998
Polarizability
41.70577256636102
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-4.923554387075869
pKa (strongest acidic)
8.0322798202448
Number of Rings
4
Rule of Five
No
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavanols

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
Flavans
Direct Parent Name
Catechin gallates
Alternative Parent Names
["1-benzopyrans", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-hydroxyflavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Alkyl aryl ethers", "Benzoyl derivatives", "Carboxylic acid esters", "Catechols", "Galloyl esters", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Oxacyclic compounds", "Polyols", "Pyrogallols and derivatives", "m-Hydroxybenzoic acid esters", "p-Hydroxybenzoic acid alkyl esters"]
External Descriptor Annotations
["Flavans, Flavanols and Leucoanthocyanidins", "catechin", "gallate ester", "polyphenol"]
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Alkyl aryl ether", "Aromatic heteropolycyclic compound", "Benzenetriol", "Benzenoid", "Benzoate ester", "Benzoic acid or derivatives", "Benzopyran", "Benzoyl", "Carboxylic acid derivative", "Carboxylic acid ester", "Catechin gallate", "Catechol", "Chromane", "Ether", "Gallic acid or derivatives", "Galloyl ester", "Hydrocarbon derivative", "Hydroxyflavonoid", "M-hydroxybenzoic acid ester", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "P-hydroxybenzoic acid alkyl ester", "P-hydroxybenzoic acid ester", "Phenol", "Polyol", "Pyrogallol derivative"]

Spectra

No spectra information available

Food Sources

NameGroup
Black teaTeas and herbal teas PublicationsShow
Green teaTeas and herbal teas PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginFormulaMonoisotopic mass
(-)-Epicatechin 3-O-gallate (Epi)catechin 3-O-gallate O-sulfatehumanileal fluid, plasmaNot AvailableC22H18O13S522.4417344 Publications
(-)-Epicatechin 3-O-gallate O-Methyl(epi)catechin-3-O-gallate O-sulfatehumanileal fluidNot AvailableC23H20O13S536.4687232 Publications
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