1.0 2010-04-08 22:12:51 UTC 2019-11-26 03:14:13 UTC FDB017114 Epicatechin 3-gallate Isolated from tea and numerous other plant subspecies inc. rhubarb and grapes. Epicatechin 3-gallate is found in many foods, some of which are cucumber, muskmelon, black raspberry, and cashew nut. (-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallate (-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallic acid (-)-Epicatechin 3-gallate (-)-Epicatechin 3-O-gallate (-)-Epicatechin gallate (-)-Epicatechin-3-gallate (-)-Epicatechin-3-O-gallate 3-Gallate(-)-epicatechol 3-Gallic acid(-)-epicatechol 3-O-Galloylepicatechin ECG Epicatechin 3-gallate Epicatechin gallate Epicatechin gallate, (2R-cis)-isomer Epicatechol, 3-gallate, (-)- Epicatechol, gallate L-Epicatechin gallate Teatannin C22H18O10 442.376 442.08999678 (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate (-)-epicatechin 3-O-gallate 1257-08-5 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=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 LSHVYAFMTMFKBA-TZIWHRDSSA-N belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin. Catechin gallates Organic compounds Phenylpropanoids and polyketides Flavonoids Flavans Aromatic heteropolycyclic compounds 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 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 Flavans, Flavanols and Leucoanthocyanidins catechin gallate ester polyphenol logp 2.55 ALOGPS logs -4.00 ALOGPS solubility 4.43e-02 g/l ALOGPS melting_point Mp 257-258° (253°) logp 3.38 ChemAxon pka_strongest_acidic 8.03 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate ChemAxon average_mass 442.376 ChemAxon mono_mass 442.08999678 ChemAxon 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 ChemAxon formula C22H18O10 ChemAxon inchi 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 ChemAxon inchikey LSHVYAFMTMFKBA-TZIWHRDSSA-N ChemAxon polar_surface_area 177.14 ChemAxon refractivity 109.76 ChemAxon polarizability 41.64 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18610 Specdb::CMs 45602 Specdb::CMs 155707 Specdb::CMs 155709 Specdb::CMs 155711 Specdb::CMs 168469 Specdb::CMs 280058 Specdb::MsMs 79422 Specdb::MsMs 79423 Specdb::MsMs 79424 Specdb::MsMs 140013 Specdb::MsMs 140014 Specdb::MsMs 140015 Specdb::MsMs 439785 Specdb::MsMs 439786 Specdb::MsMs 440504 Specdb::MsMs 440505 Specdb::MsMs 449946 Specdb::MsMs 449947 Specdb::MsMs 449948 Specdb::MsMs 449949 Specdb::MsMs 449950 Specdb::MsMs 449951 Specdb::MsMs 452117 Specdb::MsMs 2252527 Specdb::MsMs 2253941 Specdb::MsMs 2254567 Specdb::MsMs 2256018 Specdb::MsMs 2256610 Specdb::MsMs 2257963 Specdb::MsMs 2259933 Specdb::MsMs 2343779 HMDB37944 #<Reference:0x000055ce3244c6d0> Almond Type 1 specific Prunus dulcis 3755 0.0 0.0 0.0 mg/100 g Apple Type 1 specific Malus pumila 283210 0.007125 0.01425 0.0 mg/100 g Apple cider Type 2 specific 0.0 0.0 0.0 mg/100 g Apricot Type 1 specific Prunus armeniaca 36596 0.0 0.0 0.0 mg/100 g Arabica coffee Type 1 specific Coffea arabica 13443 0.0 0.0 0.0 mg/100 g Avocado Type 1 specific Persea americana 3435 0.0 0.0 0.0 mg/100 g Banana Type 1 specific Musa acuminata 4641 0.0 0.0 0.0 mg/100 g Beer Type 2 specific 0.0 0.0 0.0 mg/100 g Black raspberry Type 1 specific Rubus occidentalis 75079 0.0 0.0 0.0 mg/100 g Black tea Type 1 390.700868 1551.0 0.553333322 mg/100 g Blackcurrant Type 1 specific Ribes nigrum 78511 0.0 0.0 0.0 mg/100 g Brazil nut Type 1 specific Bertholletia excelsa 3645 0.0 0.0 0.0 mg/100 g Broad bean Type 1 specific Vicia faba 3906 0.0 0.0 0.0 mg/100 g Broccoli Type 1 specific Brassica oleracea var. italica 36774 0.0 0.0 0.0 mg/100 g Brussel sprouts Type 1 specific Brassica oleracea var. gemmifera 178616 0.0 0.0 0.0 mg/100 g Carob Type 1 specific Ceratonia siliqua 20340 Carrot Type 1 specific Daucus carota ssp. sativus 79200 0.0 0.0 0.0 mg/100 g Cashew nut Type 1 specific Anacardium occidentale 171929 0.2 0.200000008 0.200000008 mg/100 g Cauliflower Type 1 specific Brassica oleracea var. botrytis 3715 0.0 0.0 0.0 mg/100 g Chestnut Type 1 specific Castanea 21019 0.0 0.0 0.0 mg/100 g Chickpea Type 1 specific Cicer arietinum 3827 0.0 0.0 0.0 mg/100 g Chocolate Type 2 specific 0.0 0.0 0.0 mg/100 g Coffee Type 1 generic Coffea 13442 0.0 0.0 0.0 mg/100 g Common bean Type 1 specific Phaseolus vulgaris 3885 0.0 0.0 0.0 mg/100 g Common buckwheat Type 1 specific Fagopyrum esculentum 3617 Common cabbage Type 1 specific Brassica oleracea 3712 0.0 0.0 0.0 mg/100 g Common grape Type 1 specific Vitis vinifera 29760 0.962143 1.678571395 0.24571429 mg/100 g Common hazelnut Type 1 specific Corylus avellana 13451 0.0 0.0 0.0 mg/100 g Common pea Type 1 specific Pisum sativum 3888 0.0 0.0 0.0 mg/100 g Common walnut Type 1 specific Juglans regia 51240 0.0 0.0 0.0 mg/100 g Common wheat Type 1 specific Triticum aestivum 4565 0.0 0.0 0.0 mg/100 g Corn Type 1 specific Zea mays 4577 0.0 0.0 0.0 mg/100 g Cucumber Type 1 specific Cucumis sativus 3659 0.0 0.0 0.0 mg/100 g Cucurbita Type 1 specific Cucurbita 3660 0.0 0.0 0.0 mg/100 g Custard apple Type 1 specific Annona reticulata 301862 0.04 0.039999999 0.039999999 mg/100 g Eggplant Type 1 specific Solanum melongena 4111 0.0 0.0 0.0 mg/100 g European cranberry Type 1 specific Vaccinium oxycoccos 516948 0.0 0.0 0.0 mg/100 g European plum Type 1 specific Prunus domestica 3758 0.0 0.0 0.0 mg/100 g Fig Type 1 specific Ficus carica 3494 0.0 0.0 0.0 mg/100 g Garden rhubarb Type 1 specific Rheum rhabarbarum 3621 0.6 0.600000024 0.600000024 mg/100 g Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 0.0 0.0 0.0 mg/100 g German camomile Type 1 specific Matricaria recutita 127986 0.78 0.780000016 0.780000016 mg/100 g Gooseberry Type 1 specific Ribes uva-crispa 135518 0.0 0.0 0.0 mg/100 g Grape wine Type 2 specific 0.263079 0.768402894 0.0 mg/100 g Green bean Type 1 specific Phaseolus vulgaris 3885 0.0 0.0 0.0 mg/100 g Green bell pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Green tea Type 1 390.700868 1551.0 0.553333322 mg/100 g Green vegetables Unknown generic Green zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.0 0.0 0.0 mg/100 g Herbal tea Type 1 1551.0 1551.0 1551.0 mg/100 g Highbush blueberry Type 1 specific Vaccinium corymbosum 69266 0.0 0.0 0.0 mg/100 g Hot chocolate Type 2 specific 0.0 0.0 0.0 mg/100 g Italian sweet red pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Japanese persimmon Type 1 specific Diospyros kaki 35925 0.0 0.0 0.0 mg/100 g Kiwi Type 1 specific Actinidia chinensis 3625 0.0 0.0 0.0 mg/100 g Lentils Type 1 generic Lens culinaris 3864 0.0 0.0 0.0 mg/100 g Lettuce Type 1 specific Lactuca sativa 4236 0.0 0.0 0.0 mg/100 g Macadamia nut (M. tetraphylla) Type 1 specific Macadamia tetraphylla 512563 0.0 0.0 0.0 mg/100 g Mango Type 1 specific Mangifera indica 29780 0.0 0.0 0.0 mg/100 g Medlar Type 1 specific Mespilus germanica 36616 0.23 0.229999999 0.229999999 mg/100 g Muskmelon Type 1 specific Cucumis melo 3656 0.0 0.0 0.0 mg/100 g Nectarine Type 1 specific Prunus persica var. nucipersica 323851 0.0 0.0 0.0 mg/100 g Olive Type 1 specific Olea europaea 4146 0.0 0.0 0.0 mg/100 g Oxheart cabbage Type 1 specific Brassica oleracea var. conica 0.0 0.0 0.0 mg/100 g Peach (var.) Type 1 specific Prunus persica var. persica 323852 0.005 0.01 0.0 mg/100 g Peanut Type 1 specific Arachis hypogaea 3818 0.0 0.0 0.0 mg/100 g Pear Type 1 specific Pyrus communis 23211 0.0 0.0 0.0 mg/100 g Pecan nut Type 1 specific Carya illinoinensis 32201 0.0 0.0 0.0 mg/100 g Pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Peppermint Type 1 specific Mentha X piperita 34256 9.24 9.240000129 9.240000129 mg/100 g Pine nut Type 1 specific Pinus 3337 0.0 0.0 0.0 mg/100 g Pineapple Type 1 specific Ananas comosus 4615 0.0 0.0 0.0 mg/100 g Pistachio Type 1 specific Pistacia vera 55513 0.0 0.0 0.0 mg/100 g Pomegranate Type 1 specific Punica granatum 22663 0.0 0.0 0.0 mg/100 g Potato Type 1 specific Solanum tuberosum 4113 0.0 0.0 0.0 mg/100 g Quince Type 1 specific Cydonia oblonga 36610 0.0 0.0 0.0 mg/100 g Red beetroot Type 1 specific Beta vulgaris var. rubra 0.0 0.0 0.0 mg/100 g Red bell pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Red raspberry Type 1 specific Rubus idaeus 32247 0.0 0.0 0.0 mg/100 g Red tea Type 1 1551.0 1551.0 1551.0 mg/100 g Redcurrant Type 1 specific Ribes rubrum 175228 0.0 0.0 0.0 mg/100 g Robusta coffee Type 1 specific Coffea canephora 49390 0.0 0.0 0.0 mg/100 g Rubus (Blackberry, Raspberry) Type 1 specific Rubus 23216 0.0 0.0 0.0 mg/100 g Star fruit Type 1 specific Averrhoa carambola 28974 Strawberry Type 1 specific Fragaria X ananassa 3747 0.141429 0.282857146 0.0 mg/100 g Sweet cherry Type 1 specific Prunus avium 42229 0.085714 0.085714289 0.085714289 mg/100 g Sweet orange Type 1 specific Citrus sinensis 2711 0.0 0.0 0.0 mg/100 g Tea Type 1 specific Camellia sinensis 4442 224.943849 1551.0 0.553333322 mg/100 g Wheat bread Type 2 specific 0.0 0.0 0.0 mg/100 g White wine Type 2 1.52 1.52 1.52 mg/100 g Yellow wax bean Type 1 specific Phaseolus vulgaris 3885 0.0 0.0 0.0 mg/100 g Yellow zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.0 0.0 0.0 mg/100 g bitter Acetyl-CoA-carboxylase inhibitor 19 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Alpha-amylase inhibitor 44 An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-amylase (EC 3.2.1.1). Angiotensin converting enzyme inhibitor 18 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). Anti cariogenic 165 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti hepatotoxic 328 Any compound that is able to prevent damage to the liver. Anti HIV 333 A substance that destroys or inhibits replication of viruses. Anti peroxidant 519 Anti-mutagenic 451 Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Anti-viral 689 A substance that destroys or inhibits replication of viruses. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Catechol O-methyltransferase inhibitor 782 An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6). Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. Glucosyl-transferase inhibitor 953 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Immunostimulant 1032 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity. Lipoxygenase inhibitor 1077 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. Methyl-guanidine inhibitor 1103 A substance that diminishes the rate of a chemical reaction. Mitogen 1107 A chemical substance that encourages a cell to commence cell division, triggering mitosis. Nephroprotective 1147 Any protective agent that is able to prevent damage to the kidney. Xanthine oxidase inhibitor 1431 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).