Compound: (-)-Gallocatechin gallate
SMILES: O=C(O[C@H]1[C@@H](Oc2cc(O)cc(c2C1)O)c3cc(O)c(O)c(c3)O)c4cc(O)c(O)c(c4)O
InChIKey: WMBWREPUVVBILR-NQIIRXRSSA-N
Synonyms: (-)-Gallocatechin gallate, 4233-96-9, (-)-Gallocatechol gallate, Gallocatechin gallate, (-)-, (-)-gallocatechin-3-O-gallate, IRW3C4Y31Q, NVP-XAA 225, CHEBI:156271, DTXSID20195144, RefChem:390964, DTXCID30117635, 636-979-1, (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate, MFCD00214298, (-)-Gallocatechin 3-gallate, CHEMBL264938, (2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate), (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate, (-)-Gallocatechin 3-O-gallate, C22H18O11, (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate, Gallocatechol, 3-gallate, (-)-, GCG, UNII-IRW3C4Y31Q, CCRIS 9286, L-GCG, ent-Gallocatechin 3-gallate, SCHEMBL49461, Benzoic acid, 3,4,5-trihydroxy-, 3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester, (2S-trans)-, orb1303722, orb3140373, SCHEMBL30977114, CHEBI:95002, HY-N0522R, WMBWREPUVVBILR-NQIIRXRSSA-N, (2R,3S)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate, HY-N0522, MSK40201, BDBM50236531, s9058, (-)-Gallocatechin gallate (Standard), AKOS015901852, AC-6044, CCG-269313, CS-7698, EBC-474046, FG40482, NCGC00390250-01, BS-50638, DA-59404, (-)-Gallocatechin gallate, analytical standard, A11681, (-)-Gallocatechin gallate, 98%, from green tea, BRD-K19216856-001-01-9, Q27166763, (-)-Gallocatechin gallate, from green tea, >=98% (HPLC), (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl3,4,5-trihydroxybenzoate, [(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate, BENZOIC ACID, 3,4,5-TRIHYDROXY-, (2S,3R)-3,4-DIHYDRO-5,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-2H-1-BENZOPYRAN-3-YL ESTER
Theoretical properties:
molecular_formula: C22H18O11
molecular_weight: 458.4 g/mol
exact_mass: 458.08491139 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 8
hydrogen_bond_acceptor_count: 11
rotatable_bond_count: 4
heavy_atom_count: 33
topological_polar_surface_area: 197 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: (-)-gallocatechin gallate is a gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of ()-gallocatechin. A natural product found in found in green tea. It has a role as an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, an antineoplastic agent, a plant metabolite and a human xenobiotic metabolite. It is a catechin, a polyphenol and a gallate ester. It is functionally related to a gallic acid and a (-)-gallocatechin. It is an enantiomer of a (+)-gallocatechin gallate.
chebi: A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3<i>R</i>)-hydroxy group of (−)-gallocatechin. A natural product found in found in green tea.
chembl: GALLOCATECHIN GALLATE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Gallocatechin gallate (GCG) is the ester of gallocatechin and gallic acid and a type of catechin. It is an epimer of epigallocatechin gallate (EGCG).  
In a high temperature environment, an epimerization change is likely to occur, because heating results in the conversion from EGCG to GCG. According to the referenced study the resulting GCG (the epimer of EGCG) results in even lower dietary cholesterol absorption than occurs with EGCG. While this may be a beneficial outcome with respect to cholesterol reduction activity, for those wishing to maximize the EGCG content of green tea infusions, it is still appropriate to use high temperatures, as long as it is taking into account that extreme conditions will lead to small reductions in total EGCG, for example a 12.4% reduction in total EGCG when heated for 30 minutes at 100 °C.