2.0 2012-05-31 13:53:13 -0600 2015-09-13 12:56:11 -0600 ECMDB01476 M2MDB000396 3-Hydroxyanthranilic acid 3-Hydroxyanthranilic acid is an oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen. 2-Amino-3-hydroxy-Benzoate 2-Amino-3-hydroxy-Benzoic acid 2-Amino-3-hydroxybenzoate 2-Amino-3-hydroxybenzoic acid 3-Hydroxanthranilate 3-Hydroxanthranilic acid 3-Hydroxy-2-aminobenzoate 3-Hydroxy-2-aminobenzoic acid 3-Hydroxy-Anthranilate 3-Hydroxy-Anthranilic acid 3-Hydroxy-anthranilsaeure 3-Hydroxyanthranilate 3-Hydroxyanthranilic acid 3-Hydroxyantranilate 3-Hydroxyantranilic acid 3-OH-anthranilate 3-OH-anthranilic acid 3-OHAA 3-Oxyanthranilate 3-Oxyanthranilic acid C7H7NO3 153.1354 153.042593095 2-amino-3-hydroxybenzoic acid 3-hydroxyanthranilic acid 548-93-6 NC1=C(O)C=CC=C1C(O)=O InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11) WJXSWCUQABXPFS-UHFFFAOYSA-N Solid Outer membrane Inner membrane logp 0.81 ALOGPS logs -1.16 ALOGPS solubility 1.05e+01 g/l ALOGPS logp 1.15 ChemAxon pka_strongest_acidic 1.94 ChemAxon pka_strongest_basic 4.82 ChemAxon iupac 2-amino-3-hydroxybenzoic acid ChemAxon average_mass 153.1354 ChemAxon mono_mass 153.042593095 ChemAxon smiles NC1=C(O)C=CC=C1C(O)=O ChemAxon formula C7H7NO3 ChemAxon inchi InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11) ChemAxon inchikey WJXSWCUQABXPFS-UHFFFAOYSA-N ChemAxon polar_surface_area 83.55 ChemAxon refractivity 40 ChemAxon polarizability 14.18 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Tryptophan metabolism The biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan. The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoA PW000815 ec00380 Metabolic 1,4-Dichlorobenzene degradation ec00627 Microbial metabolism in diverse environments ec01120 Specdb::CMs 753 Specdb::CMs 1560 Specdb::CMs 3326 Specdb::CMs 30440 Specdb::CMs 31338 Specdb::CMs 31860 Specdb::CMs 32255 Specdb::CMs 38087 Specdb::CMs 134190 Specdb::CMs 141924 Specdb::NmrOneD 1713 Specdb::NmrOneD 4675 Specdb::NmrOneD 4700 Specdb::NmrOneD 4811 Specdb::NmrOneD 4812 Specdb::NmrOneD 9402 Specdb::NmrOneD 9403 Specdb::NmrOneD 9404 Specdb::NmrOneD 9405 Specdb::NmrOneD 9406 Specdb::NmrOneD 9407 Specdb::NmrOneD 9408 Specdb::NmrOneD 9409 Specdb::NmrOneD 9410 Specdb::NmrOneD 9411 Specdb::NmrOneD 9412 Specdb::NmrOneD 9413 Specdb::NmrOneD 9414 Specdb::NmrOneD 9415 Specdb::NmrOneD 9416 Specdb::NmrOneD 9417 Specdb::NmrOneD 9418 Specdb::NmrOneD 9419 Specdb::NmrOneD 9420 Specdb::NmrOneD 9421 Specdb::MsMs 1595 Specdb::MsMs 1596 Specdb::MsMs 1597 Specdb::MsMs 178992 Specdb::MsMs 178993 Specdb::MsMs 178994 Specdb::MsMs 181317 Specdb::MsMs 181318 Specdb::MsMs 181319 Specdb::MsMs 374892 Specdb::MsMs 437041 Specdb::MsMs 437042 Specdb::MsMs 437043 Specdb::MsMs 437044 Specdb::MsMs 440146 Specdb::MsMs 445159 Specdb::MsMs 445160 Specdb::MsMs 445161 Specdb::MsMs 445162 Specdb::MsMs 451633 Specdb::MsMs 2226469 Specdb::MsMs 2228237 Specdb::MsMs 2228901 Specdb::MsMs 2230557 Specdb::MsMs 2231340 Specdb::NmrTwoD 1654 HMDB01476 86 84 C00632 15793 3-HYDROXY-ANTHRANILATE 3HA 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 Calandra P: Research on tryptophan metabolites &quot;via kynurenine&quot; in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. 1244085 De Antoni A, Rubaltelli FF, Costa C, Allegri G: Effect of phototherapy on the urinary excretion of tryptophan metabolites in neonatal hyperbilirubinemia. Acta Vitaminol Enzymol. 1975;29(1-6):145-50. 1244083 Hegedus ZL, Frank HA, Altschule MD, Nayak U: Human plasma lipofuscin melanins formed from tryptophan metabolites. Arch Int Physiol Biochim. 1986 Dec;94(5):339-48. 2440410 Werner ER, Lutz H, Fuchs D, Hausen A, Huber C, Niederwieser D, Pfleiderer W, Reibnegger G, Troppmair J, Wachter H: Identification of 3-hydroxyanthranilic acid in mixed lymphocyte cultures. Biol Chem Hoppe Seyler. 1985 Jan;366(1):99-102. 3159398 Teulings FA, Mulder-Kooy GE, Peters HA, Fokkens W, Van Der Werf-Messing B: The excretion of 3-hydroxyanthranilic acid in patients with bladder and kidney carcinoma. Acta Vitaminol Enzymol. 1975;29(1-6):108-12. 1244078 Lopez AS, Alegre E, LeMaoult J, Carosella E, Gonzalez A: Regulatory role of tryptophan degradation pathway in HLA-G expression by human monocyte-derived dendritic cells. Mol Immunol. 2006 Jul;43(14):2151-60. Epub 2006 Feb 21. 16490253 Yeh JK, Brown RR: Effects of vitamin B-6 deficiency and tryptophan loading on urinary excretion of tryptophan metabolites in mammals. J Nutr. 1977 Feb;107(2):261-71. 833687 Herve C, Beyne P, Jamault H, Delacoux E: Determination of tryptophan and its kynurenine pathway metabolites in human serum by high-performance liquid chromatography with simultaneous ultraviolet and fluorimetric detection. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):157-61. 8634758 Teulings FA, Lems PH, Portengen H, Henkelman MS, Blonk DI: The action of 3-hydroxyanthranilic acid and other tryptophan metabolites on stimulated human lymphocytes. Acta Vitaminol Enzymol. 1975;29(1-6):113-6. 1244079 Warnell, J. L. 3-Hydroxyanthranilic acid. Biochemical Preparations (1958), 6 20-4. http://hmdb.ca/system/metabolites/msds/000/001/338/original/HMDB01476.pdf?1358462242 Catalase-peroxidase P13029 KATG_ECOLI katG http://ecmdb.ca/proteins/P13029.xml Catalase HPII P21179 CATE_ECOLI katE http://ecmdb.ca/proteins/P21179.xml 2 3-Hydroxyanthranilic acid + 4 Oxygen <> Cinnavalininate +2 Superoxide anion +2 Hydrogen peroxide +2 Hydrogen ion R02670