2.02012-05-31 13:53:13 -06002015-09-13 12:56:11 -0600ECMDB01476M2MDB0003963-Hydroxyanthranilic acid3-Hydroxyanthranilic acid is an oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.2-Amino-3-hydroxy-Benzoate2-Amino-3-hydroxy-Benzoic acid2-Amino-3-hydroxybenzoate2-Amino-3-hydroxybenzoic acid3-Hydroxanthranilate3-Hydroxanthranilic acid3-Hydroxy-2-aminobenzoate3-Hydroxy-2-aminobenzoic acid3-Hydroxy-Anthranilate3-Hydroxy-Anthranilic acid3-Hydroxy-anthranilsaeure3-Hydroxyanthranilate3-Hydroxyanthranilic acid3-Hydroxyantranilate3-Hydroxyantranilic acid3-OH-anthranilate3-OH-anthranilic acid3-OHAA3-Oxyanthranilate3-Oxyanthranilic acidC7H7NO3153.1354153.0425930952-amino-3-hydroxybenzoic acid3-hydroxyanthranilic acid548-93-6NC1=C(O)C=CC=C1C(O)=OInChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)WJXSWCUQABXPFS-UHFFFAOYSA-NSolidOuter membraneInner membranelogp0.81logs-1.16solubility1.05e+01 g/llogp1.15pka_strongest_acidic1.94pka_strongest_basic4.82iupac2-amino-3-hydroxybenzoic acidaverage_mass153.1354mono_mass153.042593095smilesNC1=C(O)C=CC=C1C(O)=OformulaC7H7NO3inchiInChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)inchikeyWJXSWCUQABXPFS-UHFFFAOYSA-Npolar_surface_area83.55refractivity40polarizability14.18rotatable_bond_count1acceptor_count4donor_count3physiological_charge-1formal_charge0Tryptophan metabolismThe 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
PW000815ec00380Metabolic1,4-Dichlorobenzene degradationec00627Microbial metabolism in diverse environmentsec01120Specdb::CMs753Specdb::CMs1560Specdb::CMs3326Specdb::CMs30440Specdb::CMs31338Specdb::CMs31860Specdb::CMs32255Specdb::CMs38087Specdb::CMs134190Specdb::CMs141924Specdb::NmrOneD1713Specdb::NmrOneD4675Specdb::NmrOneD4700Specdb::NmrOneD4811Specdb::NmrOneD4812Specdb::NmrOneD9402Specdb::NmrOneD9403Specdb::NmrOneD9404Specdb::NmrOneD9405Specdb::NmrOneD9406Specdb::NmrOneD9407Specdb::NmrOneD9408Specdb::NmrOneD9409Specdb::NmrOneD9410Specdb::NmrOneD9411Specdb::NmrOneD9412Specdb::NmrOneD9413Specdb::NmrOneD9414Specdb::NmrOneD9415Specdb::NmrOneD9416Specdb::NmrOneD9417Specdb::NmrOneD9418Specdb::NmrOneD9419Specdb::NmrOneD9420Specdb::NmrOneD9421Specdb::MsMs1595Specdb::MsMs1596Specdb::MsMs1597Specdb::MsMs178992Specdb::MsMs178993Specdb::MsMs178994Specdb::MsMs181317Specdb::MsMs181318Specdb::MsMs181319Specdb::MsMs374892Specdb::MsMs437041Specdb::MsMs437042Specdb::MsMs437043Specdb::MsMs437044Specdb::MsMs440146Specdb::MsMs445159Specdb::MsMs445160Specdb::MsMs445161Specdb::MsMs445162Specdb::MsMs451633Specdb::MsMs2226469Specdb::MsMs2228237Specdb::MsMs2228901Specdb::MsMs2230557Specdb::MsMs2231340Specdb::NmrTwoD1654HMDB014768684C00632157933-HYDROXY-ANTHRANILATE3HAKanehisa, 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-D114.22080510Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60.1244085De 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):145-50.1244083Hegedus ZL, Frank HA, Altschule MD, Nayak U: Human plasma lipofuscin melanins formed from tryptophan metabolites. Arch Int Physiol Biochim. 1986 Dec;94(5):339-48.2440410Werner 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):99-102.3159398Teulings 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):108-12.1244078Lopez 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 21.16490253Yeh 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):261-71.833687Herve 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):157-61.8634758Teulings 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):113-6.1244079Warnell, J. L. 3-Hydroxyanthranilic acid. Biochemical Preparations (1958), 6 20-4.http://hmdb.ca/system/metabolites/msds/000/001/338/original/HMDB01476.pdf?1358462242Catalase-peroxidaseP13029KATG_ECOLIkatGhttp://ecmdb.ca/proteins/P13029.xmlCatalase HPIIP21179CATE_ECOLIkatEhttp://ecmdb.ca/proteins/P21179.xml2 3-Hydroxyanthranilic acid + 4 Oxygen <> Cinnavalininate +2 Superoxide anion +2 Hydrogen peroxide +2 Hydrogen ionR02670