2.02012-05-31 14:54:10 -06002015-06-03 17:20:24 -0600ECMDB21005M2MDB001425CinnavalininateCinnavalininate 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-dicarboxylate2-Amino-3-oxo-3H-phenoxazin-1,9-dicarboxylic acid2-Amino-3H-phenoxazin-one-1,9-dicarboxylate2-Amino-3H-phenoxazin-one-1,9-dicarboxylic acidCinnabarinateCinnabarinic acidCinnavalininic acidC14H8N2O6300.2231300.0382359982-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acidcinnabarinic acidNC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=OInChI=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-NSolidOuter membraneInner membranelogp0.70logs-3.31solubility1.46e-01 g/llogp0.44pka_strongest_acidic2.37pka_strongest_basic-1.7iupac2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acidaverage_mass300.2231mono_mass300.038235998smilesNC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=OformulaC14H8N2O6inchiInChI=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)inchikeyFSBKJYLVDRVPTK-UHFFFAOYSA-Npolar_surface_area139.28refractivity76.9polarizability27.38rotatable_bond_count2acceptor_count8donor_count3physiological_charge-2formal_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
PW000815ec00380MetabolicSpecdb::CMs25286Specdb::CMs38706Specdb::CMs133571Specdb::CMs141305Specdb::NmrOneD258368Specdb::NmrOneD258369Specdb::NmrOneD258370Specdb::NmrOneD258371Specdb::NmrOneD258372Specdb::NmrOneD258373Specdb::NmrOneD258374Specdb::NmrOneD258375Specdb::NmrOneD258376Specdb::NmrOneD258377Specdb::NmrOneD258378Specdb::NmrOneD258379Specdb::NmrOneD258380Specdb::NmrOneD258381Specdb::NmrOneD258382Specdb::NmrOneD258383Specdb::NmrOneD258384Specdb::NmrOneD258385Specdb::NmrOneD258386Specdb::NmrOneD258387Specdb::MsMs28934Specdb::MsMs28935Specdb::MsMs28936Specdb::MsMs35492Specdb::MsMs35493Specdb::MsMs35494Specdb::MsMs2367385Specdb::MsMs2367386Specdb::MsMs2367387Specdb::MsMs2598634Specdb::MsMs2598635Specdb::MsMs2598636HMDB04078114918102864C05640Kanehisa, 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-D114.22080510Catalase-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