2.0 2012-05-31 14:26:38 -0600 2015-09-17 15:41:54 -0600 ECMDB20085 M2MDB000933 4-Amino-4-deoxychorismate 4-amino-4-deoxychorismate (or ADC) can be classified as a member of the Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups. ADC is involved in antibiotic biosynthesis. In some antibiotic producers, p-aminobenzoic acid (PABA) or its immediate precursor, 4-amino-4-deoxychorismate (ADC), is involved in primary metabolism and antibiotic biosynthesis. (PMID 19389784) In Escherichia coli, the production of PABA is catalyzed by the PabC protein, a beta-lyase that converts 4-amino-4-deoxychorismate (ADC)--the reaction product of the PabA and PabB enzymes--to PABA and pyruvate. (PMID 15500462) 4-Amino-4-deoxychorismate lyase (ADCL) is a member of the fold-type IV of PLP dependent enzymes that converts 4-amino-4-deoxychorismate (ADC) to p-aminobenzoate and pyruvate. (PMID 10876155) 4-Amino-4-deoxychorismic acid ADC ADCA C10H10NO5 224.193 224.056446006 (3R,4R)-4-amino-3-[(1-carboxyeth-1-en-1-yl)oxy]cyclohexa-1,5-diene-1-carboxylic acid 4-amino-4-deoxychorismic acid 133442-18-9 [H][C@@]1(N)C=CC(=C[C@@]1([H])OC(=C)C([O-])=O)C(O)=O InChI=1S/C10H11NO5/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8H,1,11H2,(H,12,13)(H,14,15)/p-1/t7-,8-/m1/s1 OIUJHGOLFKDBSU-HTQZYQBOSA-M Cytosol logp -2.33 ALOGPS logs -1.29 ALOGPS solubility 1.16e+01 g/l ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 3.24 ChemAxon pka_strongest_basic 9.12 ChemAxon iupac (3R,4R)-4-amino-3-[(1-carboxyeth-1-en-1-yl)oxy]cyclohexa-1,5-diene-1-carboxylic acid ChemAxon average_mass 224.193 ChemAxon mono_mass 224.056446006 ChemAxon smiles [H][C@@]1(N)C=CC(=C[C@@]1([H])OC(=C)C([O-])=O)C(O)=O ChemAxon formula C10H10NO5 ChemAxon inchi InChI=1S/C10H11NO5/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8H,1,11H2,(H,12,13)(H,14,15)/p-1/t7-,8-/m1/s1 ChemAxon inchikey OIUJHGOLFKDBSU-HTQZYQBOSA-M ChemAxon polar_surface_area 109.85 ChemAxon refractivity 55.97 ChemAxon polarizability 20.91 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Folate biosynthesis The biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate. Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid. (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate. This product goes on to a one carbon pool by folate pathway. PW000908 ec00790 Metabolic <i>p</i>-aminobenzoate biosynthesis PWY-6543 Specdb::CMs 2729 Specdb::NmrOneD 247848 Specdb::NmrOneD 247849 Specdb::NmrOneD 247850 Specdb::NmrOneD 247851 Specdb::NmrOneD 247852 Specdb::NmrOneD 247853 Specdb::NmrOneD 247854 Specdb::NmrOneD 247855 Specdb::NmrOneD 247856 Specdb::NmrOneD 247857 Specdb::NmrOneD 247858 Specdb::NmrOneD 247859 Specdb::NmrOneD 247860 Specdb::NmrOneD 247861 Specdb::NmrOneD 247862 Specdb::NmrOneD 247863 Specdb::NmrOneD 247864 Specdb::NmrOneD 247865 Specdb::NmrOneD 247866 Specdb::NmrOneD 247867 Specdb::MsMs 24866 Specdb::MsMs 24867 Specdb::MsMs 24868 Specdb::MsMs 31424 Specdb::MsMs 31425 Specdb::MsMs 31426 Specdb::MsMs 3608122 Specdb::MsMs 3608123 Specdb::MsMs 3608124 Specdb::MsMs 3608125 Specdb::MsMs 3608126 Specdb::MsMs 3608127 443142 391414 C11355 35181 4-AMINO-4-DEOXYCHORISMATE 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Zhang, Y., Bai, L., Deng, Z. (2009). "Functional characterization of the first two actinomycete 4-amino-4-deoxychorismate lyase genes." Microbiology 155:2450-2459. 19389784 Basset, G. J., Ravanel, S., Quinlivan, E. P., White, R., Giovannoni, J. J., Rebeille, F., Nichols, B. P., Shinozaki, K., Seki, M., Gregory, J. F. 3rd, Hanson, A. D. (2004). "Folate synthesis in plants: the last step of the p-aminobenzoate branch is catalyzed by a plastidial aminodeoxychorismate lyase." Plant J 40:453-461. 15500462 Para-aminobenzoate synthase glutamine amidotransferase component II P00903 PABA_ECOLI pabA http://ecmdb.ca/proteins/P00903.xml Para-aminobenzoate synthase component 1 P05041 PABB_ECOLI pabB http://ecmdb.ca/proteins/P05041.xml Aminodeoxychorismate lyase P28305 PABC_ECOLI pabC http://ecmdb.ca/proteins/P28305.xml Chorismate + L-Glutamine <> 4-Amino-4-deoxychorismate + L-Glutamate R01716 PABASYN-RXN 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acid R05553 ADCLY-RXN 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Pyruvic acid R05553 Chorismate + L-Glutamine > 4-Amino-4-deoxychorismate + L-Glutamate 4-Amino-4-deoxychorismate > p-Aminobenzoic acid + Pyruvic acid 4-amino-4-deoxychorismate + 4-Amino-4-deoxychorismate > Pyruvic acid + Hydrogen ion + p-Aminobenzoic acid PW_R003402 Chorismate + L-Glutamine > L-Glutamic acid + 4-amino-4-deoxychorismate + L-Glutamate + 4-Amino-4-deoxychorismate PW_R003403 Chorismate + L-Glutamine <>4 4-Amino-4-deoxychorismate + L-Glutamate 4 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acid Chorismate + L-Glutamine <>4 4-Amino-4-deoxychorismate + L-Glutamate