PhytoHub: Showing entry for (-)-Epigallocatechin 3-O-gallate

(-)-Epigallocatechin 3-O-gallate

Identification

PhytoHub ID

PHUB000265

Name

(-)-Epigallocatechin 3-O-gallate

Systematic Name

(−)-Epigallocatechin-3-O-gallate

Synonyms

EGCG

CAS Number

Not Available

Average Mass

458.375

Monoisotopic Mass

458.0849114

Chemical Formula

C₂₂H₁₈O₁₁

IUPAC Name

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

InChI Key

WMBWREPUVVBILR-PUUMMNGONA-N

InChI Identifier

InChI=1/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/s2

SMILES

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

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 7.28e-02 g/l
LogS (ALOGPS): -3.80
LogP (ALOGPS): 2.38
Hydrogen Acceptors: 10
Hydrogen Donors: 8
Rotatable Bond Count: 4
Polar Surface Area: 197.36999999999998
Refractivity: 111.74529999999999
Polarizability: 42.62355309481916
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -5.423934990004845
pKa (strongest acidic): 7.992993558286566
Number of Rings: 4
Rule of Five: No
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

No external links

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Flavonoids
Sub-class: Flavanols

Spectra from Online Resources

Record ID	Source	Description	View
TY000083	MassBank	LC-ESI-ITTOF Spectrum - -, [M+H]+	View Spectra

Food Sources

	Name	Group
	Black tea	Teas and herbal teas	Publications	Show
	Green tea	Teas and herbal teas	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food Phytochemical	Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
(-)-Epigallocatechin 3-O-gallate	(-)-Epigallocatechin 3-O-gallate	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₂₂H₁₈O₁₁	458.0849114	Detailed Intervention Studies
(-)-Epigallocatechin 3-O-gallate	(Epi)gallocatechin-3-O-gallate O-sulfate	human	ileal fluid, plasma	Not Available	Not Available	Not Available	Not Available	C₂₂H₁₈O₁₄S	538.4410395		Publications
(-)-Epigallocatechin 3-O-gallate	O-Methyl(epi)gallocatechin-3-O-gallate O-sulfate	human	ileal fluid	Not Available	Not Available	Not Available	Not Available	C₂₃H₂₀O₁₄S	552.4680283		Publications
(-)-Epigallocatechin 3-O-gallate	5-(3’,4’,5’-trihydroxyphenyl)-gamma-valerolactone	human	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₂O₅	224.068473486		Publications
(-)-Epigallocatechin 3-O-gallate	5-(Phenyl)-γ-valerolactone-sulfate-glucuronide	human	plasma, urine	host-gut microbiota co-metabolite	3h-5h	<20 nmol/L	<1%				Publications
Red Wine Flavan-3-ols	(-)-Epigallocatechin 3-O-gallate	human	plasma	unchanged	1h-3h	0.5-2µmol/L	Not Available	C₂₂H₁₈O₁₁	458.0849114		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value
	(-)-Epigallocatechin 3-O-gallate		5-(Phenyl)-γ-valerolactone-sulfate-glucuronide	Microbiota	Effect, clusters	Publications
	Red Wine Flavan-3-ols		(-)-Epigallocatechin 3-O-gallate	Genotype	No effect	Publications

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Showing entry for (-)-Epigallocatechin 3-O-gallate