precursor

Showing entry for (-)-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-WIYYLYMNSA-N
InChI Identifier
InChI=1S/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-/m1/s1
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

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavan-3-ols

Spectra from Phytohub

Spectrum TypeInstrument TypeTechnologyIon ModeCollision EnergyView
LC-MS/MSLC-ESI-QTOFBruker MaxisPositive40VView Spectrum
LC-MS/MSLC-ESI-QTOFBruker MaxisNegative40VView Spectrum
LC-MS/MSLC-ESI-QTOFBruker MaxisNegative20VView Spectrum
LC-MS/MSLC-ESI-QTOFBruker MaxisPositive20VView Spectrum
LC-MS/MSLC-ESI-QTOFBruker MaxisPositive10VView Spectrum
LC-MS/MSLC-ESI-QTOFBruker MaxisNegative10VView Spectrum
LC-MS/MSLC-ESI-QTOFBruker Impact HDNegative30VView Spectrum
LC-MS/MSLC-ESI-QTOFBruker Impact HDNegative10VView Spectrum
LC-MS/MSLC-ESI-QTOFBruker Impact HDNegative50VView Spectrum
LC-MS/MSLC-ESI-QTOFBruker Impact HDNegative40VView Spectrum
LC-MS/MSLC-ESI-QTOFBruker Impact HDNegative20VView Spectrum
LC-MS/MSLC-ESI-QFTThermo Fisher Scientific Q-ExactivePositive60VView Spectrum
LC-MS/MSLC-ESI-QFTThermo Fisher Scientific Q-ExactiveNegative45VView Spectrum
LC-MS/MSLC-ESI-QFTThermo Fisher Scientific Q-ExactivePositive45VView Spectrum
LC-MS/MSLC-ESI-QFTThermo Fisher Scientific Q-ExactiveNegative60VView Spectrum
LC-MS/MSLC-ESI-QFTThermo Fisher Scientific Q-ExactiveNegative15VView Spectrum
LC-MS/MSLC-ESI-QFTThermo Fisher Scientific Q-ExactivePositive15VView Spectrum
LC-MS/MSLC-ESI-QFTThermo Fisher Scientific Q-ExactiveNegative30VView Spectrum
LC-MS/MSLC-ESI-QTOFWaters Xevo G2Positive6VView Spectrum
LC-MS/MSLC-ESI-QTOFWaters Xevo G2Negative6VView Spectrum
LC-MS/MSLC-ESI-QTOFWaters Xevo G2Negative6VView Spectrum
LC-MS/MSLC-ESI-QTOFWaters Xevo G2Negative6VView Spectrum
LC-MS/MSLC-ESI-QTOFWaters Xevo G2Positive6VView Spectrum
LC-MS/MSLC-ESI-QTOFWaters Xevo G2Positive6VView Spectrum
LC-MS/MSLC-ESI-QTOFWaters Xevo G2Positive6VView Spectrum

Food Sources

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

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
(-)-Epigallocatechin 3-O-gallate (-)-Epigallocatechin 3-O-gallatehumanplasmaunchanged1h-3h0.5-2µmol/LNot AvailableC22H18O11458.0849114 Detailed Intervention Studies Publications
(-)-Epigallocatechin 3-O-gallate (Epi)gallocatechin-3-O-gallate O-sulfatehumanileal fluid, plasmaNot AvailableNot AvailableNot AvailableNot AvailableC22H18O14S538.4410395 Publications
(-)-Epigallocatechin 3-O-gallate O-Methyl(epi)gallocatechin-3-O-gallate O-sulfatehumanileal fluidNot AvailableNot AvailableNot AvailableNot AvailableC23H20O14S552.4680283 Publications
(-)-Epigallocatechin 3-O-gallate 5-(3’,4’,5’-trihydroxyphenyl)-gamma-valerolactonehumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC11H12O5224.068473486 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
(-)-Epigallocatechin 3-O-gallate (-)-Epigallocatechin 3-O-gallateGenotypeNo effect Publications
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