2.0 2012-05-31 13:51:31 -0600 2015-09-13 12:56:11 -0600 ECMDB01392 M2MDB000367 p-Aminobenzoic acid 4-Aminobenzoic acid, para-aminobenzoic acid, or simply PABA, is an organic compound with molecular formula C7H7NO2. PABA is a white crystalline substance that is only slightly soluble in water. It consists of a benzene ring substituted with an amino group and a carboxylic acid.; PABA is an essential nutrient for some bacteria and is sometimes called Vitamin Bx. PABA is an intermediate in the bacterial synthesis of folate. E. coli generate PABA from chorismate in a complex, multistep reaction. Note that sulfonamide drugs are structurally similar to PABA, and their antibacterial activity is due to their ability to interfere with the conversion of PABA to folate by the enzyme dihydropteroate synthetase. 1-Amino-4-carboxybenzene 4-Aminobenzoate 4-Aminobenzoic acid 4-Carboxyaniline 4-Carboxyphenylamine <i>p</i>-aminobenzoate ABEE Acido p-aminobenzoico Acidum paraminobenzoicum Actipol Amben Aminobenzoate Aminobenzoic acid Aniline-4-carboxylate Aniline-4-carboxylic acid Anti-Chromotrichia factor Anticanitic vitamin Anticantic vitamin Antichromotrichia factor Bacterial vitamin H1 Chromotrichia factor g-Aminobenzoate g-Aminobenzoic acid Gamma-Aminobenzoate Gamma-Aminobenzoic acid Hachemina Kyselina p-aminobenzoova P-Amino-Benzoate P-Amino-Benzoic acid P-Aminobenzoate P-Aminobenzoic acid P-Carboxyaniline P-Carboxyphenylamine PAB PABA Pabacyd Pabafilm Pabagel Pabamine Pabanol Papacidum Para-aminobenzoate Para-Aminobenzoic acid Paraminol Paranate Paranic acid Potaba Romavit Rvpaba RVPaba Lipstick Sunbrella Super Shade by Coppertone Trichochromogenic factor Trochromogenic factor Vitamin BX Vitamin H' γ-Aminobenzoate γ-Aminobenzoic acid C7H7NO2 137.136 137.047678473 4-aminobenzoic acid sunbrella 150-13-0 NC1=CC=C(C=C1)C(O)=O InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10) ALYNCZNDIQEVRV-UHFFFAOYSA-N Solid Cytosol logp 0.78 ALOGPS logs -1.49 ALOGPS solubility 4.41e+00 g/l ALOGPS melting_point 188.5 oC logp 0.8 ChemAxon pka_strongest_acidic 4.77 ChemAxon pka_strongest_basic 2.69 ChemAxon iupac 4-aminobenzoic acid ChemAxon average_mass 137.136 ChemAxon mono_mass 137.047678473 ChemAxon smiles NC1=CC=C(C=C1)C(O)=O ChemAxon formula C7H7NO2 ChemAxon inchi InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10) ChemAxon inchikey ALYNCZNDIQEVRV-UHFFFAOYSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 38.01 ChemAxon polarizability 13.44 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 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 1,4-Dichlorobenzene degradation ec00627 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 <i>p</i>-aminobenzoate biosynthesis PWY-6543 tetrahydrofolate biosynthesis PWY-6614 Specdb::CMs 738 Specdb::CMs 1324 Specdb::CMs 1512 Specdb::CMs 3087 Specdb::CMs 29667 Specdb::CMs 30450 Specdb::CMs 31320 Specdb::CMs 31321 Specdb::CMs 32042 Specdb::CMs 38052 Specdb::CMs 133068 Specdb::CMs 140802 Specdb::EiMs 1958 Specdb::NmrOneD 1694 Specdb::NmrOneD 3843 Specdb::NmrOneD 4897 Specdb::MsMs 1550 Specdb::MsMs 1551 Specdb::MsMs 1552 Specdb::MsMs 5237 Specdb::MsMs 5238 Specdb::MsMs 5239 Specdb::MsMs 5240 Specdb::MsMs 5241 Specdb::MsMs 5242 Specdb::MsMs 5243 Specdb::MsMs 5244 Specdb::MsMs 5245 Specdb::MsMs 5246 Specdb::MsMs 5248 Specdb::MsMs 179463 Specdb::MsMs 179464 Specdb::MsMs 179465 Specdb::MsMs 181791 Specdb::MsMs 181792 Specdb::MsMs 181793 Specdb::MsMs 437149 Specdb::MsMs 437150 Specdb::MsMs 437151 Specdb::MsMs 437152 Specdb::MsMs 437153 Specdb::NmrTwoD 1066 Specdb::NmrTwoD 1635 HMDB01392 978 953 C00568 30753 P-AMINO-BENZOATE PAB p-Aminobenzoic 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 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 Derewlany LO, Knie B, Koren G: Arylamine N-acetyltransferase activity of the human placenta. J Pharmacol Exp Ther. 1994 May;269(2):756-60. 8182542 Laufer D, Cleghorn G, Forstner G, Ellis L, Koren G, Durie P: The bentiromide test using plasma p-aminobenzoic acid for diagnosing pancreatic insufficiency in young children. The effect of two different doses and a liquid meal. Gastroenterology. 1991 Jul;101(1):207-13. 2044909 Nathan D, Sakr A, Lichtin JL, Bronaugh RL: In vitro skin absorption and metabolism of benzoic acid, p-aminobenzoic acid, and benzocaine in the hairless guinea pig. Pharm Res. 1990 Nov;7(11):1147-51. 2293213 Lankisch PG, Brauneis J, Otto J, Goke B: Pancreolauryl and NBT-PABA tests. Are serum tests more practicable alternatives to urine tests in the diagnosis of exocrine pancreatic insufficiency? Gastroenterology. 1986 Feb;90(2):350-4. 3484456 Szewczuk A, Wellman-Bednawska M: The use of gamma-glutamyl-p-aminobenzoic acid as the substrate for determination of gamma-glutamyltranspeptidase activity in blood serum. Clin Chim Acta. 1978 Mar 1;84(1-2):19-26. 25149 Kiss Z, Wolfling J, Csati S, Nagy F, Lonovics J, Schneider G: [The ursodeoxycholic acid-p-aminobenzoic acid test in the diagnosis of small bowel bacterial overgrowth syndrome] Orv Hetil. 1997 May 18;138(20):1255-8. 9244859 Szewczuk A, Wellman-Bednawska M: Acyl derivatives of p-aminobenzoic acid as new substrates for the assay of serum acylase activity. Clin Chim Acta. 1978 Mar 1;84(1-2):27-31. 305833 Derewlany LO, Knie B, Koren G: Human placental transfer and metabolism of p-aminobenzoic acid. J Pharmacol Exp Ther. 1994 May;269(2):761-5. 8182543 Ito S, Maruta K, Imai Y, Kato T, Ito M, Nakajima S, Fujita K, Kurahashi T: Urinary p-aminobenzoic acid determined in the pancreatic function test by liquid chromatography, with electrochemical detection. Clin Chem. 1982 Feb;28(2):323-6. 6976857 Durie PR, Yung-Jato LY, Soldin SJ, Verjee Z, Ellis L: Bentiromide test using liquid-chromatographic measurement of p-aminobenzoic acid and its metabolites for diagnosing pancreatic insufficiency in childhood. J Pediatr. 1992 Sep;121(3):413-6. 1517919 Sato, Ryu; Kimura, Koichi; Takahashi, Akira. Preparation of p-aminobenzoic acid from styrene polymers. Jpn. Kokai Tokkyo Koho (2007), 13pp. http://hmdb.ca/system/metabolites/msds/000/001/254/original/HMDB01392.pdf?1358461266 Dihydropteroate synthase P0AC13 DHPS_ECOLI folP http://ecmdb.ca/proteins/P0AC13.xml Aminodeoxychorismate lyase P28305 PABC_ECOLI pabC http://ecmdb.ca/proteins/P28305.xml 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acid R05553 ADCLY-RXN p-Aminobenzoic acid + 6-Hydroxymethyl-dihydropterin pyrophosphate > 7,8-Dihydropteroic acid + Pyrophosphate H2PTEROATESYNTH-RXN 6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <> 7,8-Dihydropteroic acid + Water R03066 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + p-Aminobenzoic acid + (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate <> Pyrophosphate + 7,8-Dihydropteroic acid R03067 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Pyruvic acid R05553 Water + p-Aminobenzoyl glutamate > p-Aminobenzoic acid + L-Glutamate RXN0-5040 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine diphosphate + p-Aminobenzoic acid > Pyrophosphate + 7,8-Dihydropteroic acid 4-Amino-4-deoxychorismate > p-Aminobenzoic acid + Pyruvic acid 6-Hydroxymethyl-dihydropterin pyrophosphate + p-Aminobenzoic acid > Pyrophosphate + 7,8-Dihydropteroic acid PW_R003401 4-amino-4-deoxychorismate + 4-Amino-4-deoxychorismate > Pyruvic acid + Hydrogen ion + p-Aminobenzoic acid PW_R003402 4 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acid 6 6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <>7 7,8-Dihydropteroic acid + Water 6 6-Hydroxymethyl dihydropterin + p-Aminobenzoic acid <>7 7,8-Dihydropteroic acid + Water