2.0 2012-05-31 13:56:21 -0600 2015-09-13 12:56:12 -0600 ECMDB02260 M2MDB000452 Gallic acid Gallic acid (GA) is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. Plants, bacteria and fungi are capable of synthesizing gallic acid. Shikimate dehydrogenase (SDH), a shikimate pathway enzyme essential for aromatic amino acid synthesis, is required for gallic acid production in Escherichia coli. SDH catalyzes NADPH-dependent reduction of 3-DHS (3-dehydroshikimate) to shikimic acid (SA), which is ultimately used to produce the aromatic amino acids l-tyrosine, l-tryptophan, and l-phenylalanine. SDH also catalyzes NADP+-dependent dehydrogenation of SA to 3-DHS, but also the dehydrogenation of 3-DHS to GA. 3,4,5-Trihydroxy-Benzoate 3,4,5-Trihydroxy-Benzoic acid 3,4,5-Trihydroxybenzoate 3,4,5-Trihydroxybenzoate (acd/name 4.0) 3,4,5-Trihydroxybenzoic acid 3,4,5-trihydroxybenzoic acid (ACD/Name 4.0) Gallate Gallate polymer Gallate tech. Gallic acid Gallic acid polymer Gallic acid tech. Galop Pyrogallol-5-carboxylate Pyrogallol-5-carboxylic acid C7H6O5 170.1195 170.021523302 3,4,5-trihydroxybenzoic acid galop 149-91-7 OC(=O)C1=CC(O)=C(O)C(O)=C1 InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12) LNTHITQWFMADLM-UHFFFAOYSA-N Solid Outer membrane Inner membrane logp 1.17 ALOGPS logs -1.54 ALOGPS solubility 4.94e+00 g/l ALOGPS melting_point 258-265 oC logp 0.72 ChemAxon pka_strongest_acidic 3.94 ChemAxon pka_strongest_basic -6 ChemAxon iupac 3,4,5-trihydroxybenzoic acid ChemAxon average_mass 170.1195 ChemAxon mono_mass 170.021523302 ChemAxon smiles OC(=O)C1=CC(O)=C(O)C(O)=C1 ChemAxon formula C7H6O5 ChemAxon inchi InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12) ChemAxon inchikey LNTHITQWFMADLM-UHFFFAOYSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 39.26 ChemAxon polarizability 14.75 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon 1,4-Dichlorobenzene degradation ec00627 Microbial metabolism in diverse environments ec01120 Specdb::CMs 855 Specdb::CMs 1699 Specdb::CMs 3186 Specdb::CMs 28711 Specdb::CMs 30546 Specdb::CMs 31532 Specdb::CMs 31823 Specdb::CMs 38898 Specdb::CMs 137481 Specdb::CMs 145215 Specdb::EiMs 1600 Specdb::NmrOneD 2029 Specdb::NmrOneD 3841 Specdb::NmrOneD 4108 Specdb::NmrOneD 5016 Specdb::NmrOneD 5017 Specdb::NmrOneD 61112 Specdb::NmrOneD 61113 Specdb::NmrOneD 61114 Specdb::NmrOneD 61115 Specdb::NmrOneD 61116 Specdb::NmrOneD 61117 Specdb::NmrOneD 61118 Specdb::NmrOneD 61119 Specdb::NmrOneD 61120 Specdb::NmrOneD 61121 Specdb::NmrOneD 61122 Specdb::NmrOneD 61123 Specdb::NmrOneD 61124 Specdb::NmrOneD 61125 Specdb::NmrOneD 61126 Specdb::NmrOneD 61127 Specdb::NmrOneD 61128 Specdb::NmrOneD 61129 Specdb::NmrOneD 61130 Specdb::NmrOneD 61131 Specdb::MsMs 2454 Specdb::MsMs 2455 Specdb::MsMs 2456 Specdb::MsMs 6086 Specdb::MsMs 6087 Specdb::MsMs 6088 Specdb::MsMs 6089 Specdb::MsMs 6090 Specdb::MsMs 6091 Specdb::MsMs 179640 Specdb::MsMs 179641 Specdb::MsMs 179642 Specdb::MsMs 181974 Specdb::MsMs 181975 Specdb::MsMs 181976 Specdb::MsMs 374050 Specdb::MsMs 374068 Specdb::MsMs 437731 Specdb::MsMs 437732 Specdb::MsMs 437733 Specdb::MsMs 437734 Specdb::MsMs 437735 Specdb::MsMs 439658 Specdb::MsMs 439659 Specdb::MsMs 452005 Specdb::NmrTwoD 1964 HMDB05807 370 361 C01424 30778 CPD-183 Gallic acid Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Cheng K F; Yip C S; Yeung H W; Kong Y C Leonurine, an improved synthesis. Experientia (1979), 35(5), 571-2. PubMed ID 446644 http://hmdb.ca/system/metabolites/msds/000/005/014/original/HMDB05807.pdf?1358462371 Quinate/shikimate dehydrogenase P0A6D5 YDIB_ECOLI ydiB http://ecmdb.ca/proteins/P0A6D5.xml Shikimate dehydrogenase P15770 AROE_ECOLI aroE http://ecmdb.ca/proteins/P15770.xml