2.0 2012-05-31 14:54:10 -0600 2015-06-03 17:20:24 -0600 ECMDB21005 M2MDB001425 Cinnavalininate Cinnavalininate is an intermediate in the tryptophan metabolic pathway [Kegg: C05640]. It is generated from 3-hydroxyanthranilate via the enzyme catalase (EC:1.11.1.6). 2-Amino-3-oxo-3H-phenoxazin-1,9-dicarboxylate 2-Amino-3-oxo-3H-phenoxazin-1,9-dicarboxylic acid 2-Amino-3H-phenoxazin-one-1,9-dicarboxylate 2-Amino-3H-phenoxazin-one-1,9-dicarboxylic acid Cinnabarinate Cinnabarinic acid Cinnavalininic acid C14H8N2O6 300.2231 300.038235998 2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid cinnabarinic acid NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=O InChI=1S/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21) FSBKJYLVDRVPTK-UHFFFAOYSA-N Solid Outer membrane Inner membrane logp 0.70 ALOGPS logs -3.31 ALOGPS solubility 1.46e-01 g/l ALOGPS logp 0.44 ChemAxon pka_strongest_acidic 2.37 ChemAxon pka_strongest_basic -1.7 ChemAxon iupac 2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid ChemAxon average_mass 300.2231 ChemAxon mono_mass 300.038235998 ChemAxon smiles NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=O ChemAxon formula C14H8N2O6 ChemAxon inchi InChI=1S/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21) ChemAxon inchikey FSBKJYLVDRVPTK-UHFFFAOYSA-N ChemAxon polar_surface_area 139.28 ChemAxon refractivity 76.9 ChemAxon polarizability 27.38 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 8 ChemAxon donor_count 3 ChemAxon physiological_charge -2 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 Specdb::CMs 25286 Specdb::CMs 38706 Specdb::CMs 133571 Specdb::CMs 141305 Specdb::NmrOneD 258368 Specdb::NmrOneD 258369 Specdb::NmrOneD 258370 Specdb::NmrOneD 258371 Specdb::NmrOneD 258372 Specdb::NmrOneD 258373 Specdb::NmrOneD 258374 Specdb::NmrOneD 258375 Specdb::NmrOneD 258376 Specdb::NmrOneD 258377 Specdb::NmrOneD 258378 Specdb::NmrOneD 258379 Specdb::NmrOneD 258380 Specdb::NmrOneD 258381 Specdb::NmrOneD 258382 Specdb::NmrOneD 258383 Specdb::NmrOneD 258384 Specdb::NmrOneD 258385 Specdb::NmrOneD 258386 Specdb::NmrOneD 258387 Specdb::MsMs 28934 Specdb::MsMs 28935 Specdb::MsMs 28936 Specdb::MsMs 35492 Specdb::MsMs 35493 Specdb::MsMs 35494 Specdb::MsMs 2367385 Specdb::MsMs 2367386 Specdb::MsMs 2367387 Specdb::MsMs 2598634 Specdb::MsMs 2598635 Specdb::MsMs 2598636 HMDB04078 114918 102864 C05640 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 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