1.0 2010-04-08 22:14:02 UTC 2019-11-26 03:16:54 UTC FDB018932 Vescalagincarboxylic acid Vescalagincarboxylic acid is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Vescalagincarboxylic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Vescalagincarboxylic acid can be found in guava, which makes vescalagincarboxylic acid a potential biomarker for the consumption of this food product. Vescalagin carboxylic acid Vescalagincarboxylic acid C42H26O27 962.6396 962.066145626 7,8,9,12,13,14,25,26,27,30,31,32,35,36,37-pentadecahydroxy-4,17,22,40,44-pentaoxo-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-46-carboxylic acid 7,8,9,12,13,14,25,26,27,30,31,32,35,36,37-pentadecahydroxy-4,17,22,40,44-pentaoxo-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-46-carboxylic acid 118964-19-5 OC(=O)C1C2OC(=O)C3=C(C(O)=C(O)C(O)=C13)C1=C3C(=C(O)C(O)=C1O)C1=C(C=C(O)C(O)=C1O)C(=O)OC1COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)OC1C2OC3=O InChI=1S/C42H26O27/c43-8-1-5-12(25(49)22(8)46)13-6(2-9(44)23(47)26(13)50)40(62)67-34-11(4-65-38(5)60)66-39(61)7-3-10(45)24(48)27(51)14(7)15-19-16(29(53)32(56)28(15)52)17-20-18(31(55)33(57)30(17)54)21(37(58)59)35(68-41(20)63)36(34)69-42(19)64/h1-3,11,21,34-36,43-57H,4H2,(H,58,59) ZTOKIAYQNMCRRX-UHFFFAOYSA-N belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Hydrolyzable tannins Organic compounds Phenylpropanoids and polyketides Tannins Hydrolyzable tannins Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 2-benzopyrans Carbonyl compounds Carboxylic acid esters Carboxylic acids Gallic acid and derivatives Hexacarboxylic acids and derivatives Hydrocarbon derivatives Lactones Organic oxides Oxacyclic compounds Polyols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2-benzopyran Aromatic heteropolycyclic compound Benzenoid Benzopyran Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Gallic acid or derivatives Hexacarboxylic acid or derivatives Hydrocarbon derivative Hydrolyzable tannin Isochromane Lactone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Polyol logp 3.07 ALOGPS logs -2.14 ALOGPS solubility 7.01e+00 g/l ALOGPS melting_point Mp 180° dec. logp 2.32 ChemAxon pka_strongest_acidic 2.92 ChemAxon pka_strongest_basic -6.2 ChemAxon iupac 7,8,9,12,13,14,25,26,27,30,31,32,35,36,37-pentadecahydroxy-4,17,22,40,44-pentaoxo-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-46-carboxylic acid ChemAxon average_mass 962.6396 ChemAxon mono_mass 962.066145626 ChemAxon smiles OC(=O)C1C2OC(=O)C3=C(C(O)=C(O)C(O)=C13)C1=C3C(=C(O)C(O)=C1O)C1=C(C=C(O)C(O)=C1O)C(=O)OC1COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)OC1C2OC3=O ChemAxon formula C42H26O27 ChemAxon inchi InChI=1S/C42H26O27/c43-8-1-5-12(25(49)22(8)46)13-6(2-9(44)23(47)26(13)50)40(62)67-34-11(4-65-38(5)60)66-39(61)7-3-10(45)24(48)27(51)14(7)15-19-16(29(53)32(56)28(15)52)17-20-18(31(55)33(57)30(17)54)21(37(58)59)35(68-41(20)63)36(34)69-42(19)64/h1-3,11,21,34-36,43-57H,4H2,(H,58,59) ChemAxon inchikey ZTOKIAYQNMCRRX-UHFFFAOYSA-N ChemAxon polar_surface_area 472.25 ChemAxon refractivity 217.56 ChemAxon polarizability 84.13 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 22 ChemAxon donor_count 16 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 83205 Specdb::MsMs 83206 Specdb::MsMs 83207 Specdb::MsMs 144753 Specdb::MsMs 144754 Specdb::MsMs 144755 Specdb::MsMs 3606413 Specdb::MsMs 3606414 Specdb::MsMs 3606415 Specdb::MsMs 3606416 Specdb::MsMs 3606417 Specdb::MsMs 3606418 Guava Type 1 specific Psidium guajava 120290 Topoisomerase-II inhibitor 1366 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.