2.0 2015-06-08 15:28:30 -0600 2015-08-05 16:22:05 -0600 ECMDB23870 M2MDB005520 Aromatic amino acid Amino acids that include an aromatic ring (+-)-5-Hydroxytryptophan (S)-5-Hydroxytryptophan 5-HTP 5-Hydroxy-DL-tryptophan 5-Hydroxy-tryptophan 5-Hydroxyl-L-tryptophan 5-Hydroxytryptophan 5-Hydroxytryptophan DL-form 5-Hydroxytryptophan L form 5-Hydroxytryptophan L-form Cincofarm DL-5-HTP DL-5-Hydroxytryptophan Hydroxytryptophan L-5-Hydroxytryptophan Levothym Levotinine Oxitriptan Oxyfan Oxytryptophan Pretonine Quietim Serotonyl Telesol Triptene C11H12N2O3 220.2246 220.08479226 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid DL-5-hydroxytryptophan NC(CC1=CNC2=C1C=C(O)C=C2)C(O)=O InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16) LDCYZAJDBXYCGN-UHFFFAOYSA-N logp -1.56 ALOGPS logs -1.78 ALOGPS solubility 3.63e+00 g/l ALOGPS logp -1.4 ChemAxon pka_strongest_acidic 2.15 ChemAxon pka_strongest_basic 9.18 ChemAxon iupac 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid ChemAxon average_mass 220.2246 ChemAxon mono_mass 220.08479226 ChemAxon smiles NC(CC1=CNC2=C1C=C(O)C=C2)C(O)=O ChemAxon formula C11H12N2O3 ChemAxon inchi InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16) ChemAxon inchikey LDCYZAJDBXYCGN-UHFFFAOYSA-N ChemAxon polar_surface_area 99.34 ChemAxon refractivity 58.18 ChemAxon polarizability 22.03 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 Tyrosine metabolism ec00350 Phenylalanine metabolism The pathways of the metabolism of phenylalaline begins with the conversion of chorismate to prephenate through a P-protein (chorismate mutase:pheA). Prephenate then interacts with a hydrogen ion through the same previous enzyme resulting in a release of carbon dioxide, water and a phenolpyruvic acid. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosine. Phenolpyruvic acid can also be obtained from a reversivle reaction with ammonia, a reduced acceptor and a D-amino acid dehydrogenase, resulting in a water, an acceptor and a D-phenylalanine, which can be then transported into the periplasmic space by aromatic amino acid exporter. L-phenylalanine also interacts in two reversible reactions, one involved with oxygen through a catalase peroxidase resulting in a carbon dioxide and 2-phenylacetamide. The other reaction involved an interaction with oxygen through a phenylalanine aminotransferase resulting in a oxoglutaric acid and phenylpyruvic acid. L-phenylalanine can be imported into the cytoplasm through an aromatic amino acid:H+ symporter AroP. The compound can also be imported into the periplasmic space through a transporter: L-amino acid efflux transporter. PW000921 ec00360 Metabolic Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Novobiocin biosynthesis ec00401 Isoquinoline alkaloid biosynthesis ec00950 Tropane, piperidine and pyridine alkaloid biosynthesis ec00960 Lysine biosynthesis Lysine is biosynthesized from L-aspartic acid. L-aspartic acid can be incorporated into the cell through various methods: C4 dicarboxylate / orotate:H+ symporter , glutamate / aspartate : H+ symporter GltP, dicarboxylate transporter , C4 dicarboxylate / C4 monocarboxylate transporter DauA, glutamate / aspartate ABC transporter L-aspartic acid is phosphorylated by an ATP-driven Aspartate kinase resulting in ADP and L-aspartyl-4-phosphate. L-aspartyl-4-phosphate is then dehydrogenated through an NADPH driven aspartate semialdehyde dehydrogenase resulting in a release of phosphate, NADP and L-aspartic 4-semialdehyde (involved in methionine biosynthesis). L-aspartic 4-semialdehyde interacts with a pyruvic acid through a 4-hydroxy-tetrahydrodipicolinate synthase resulting in a release of hydrogen ion, water and (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate. The latter compound is then reduced by an NADPH driven 4-hydroxy-tetrahydrodipicolinate reductase resulting in a release of water, NADP and (S)-2,3,4,5-tetrahydrodipicolinate, This compound interacts with succinyl-CoA and water through a tetrahydrodipicolinate succinylase resulting in a release of coenzyme A and N-Succinyl-2-amino-6-ketopimelate. This compound interacts with L-glutamic acid through a N-succinyldiaminopimelate aminotransferase resulting in oxoglutaric acid, N-succinyl-L,L-2,6-diaminopimelate. The latter compound is then desuccinylated by reacting with water through a N-succinyl-L-diaminopimelate desuccinylase resulting in a succinic acid and L,L-diaminopimelate. This compound is then isomerized through a diaminopimelate epimerase resulting in a meso-diaminopimelate (involved in peptidoglyccan biosynthesis I). This compound is then decarboxylated by a diaminopimelate decarboxylase resulting in a release of carbon dioxide and L-lysine. L-lysine is then incorporated into lysine degradation pathway. Lysine also regulate its own biosynthesis by repressing dihydrodipicolinate synthase and also repressing lysine-sensitive aspartokinase 3. A metabolic connection joins synthesis of an amino acid, lysine, to synthesis of cell wall material. Diaminopimelate is a precursor both for lysine and for cell wall components. The synthesis of lysine, methionine and threonine share two reactions at the start of the three pathways, the reactions converting L-aspartate to L-aspartate semialdehyde. The reaction involving aspartate kinase is carried out by three isozymes, one specific for synthesis of each end product amino acid. Each of the three aspartate kinase isozymes is regulated by its corresponding end product amino acid. PW000771 ec00300 Metabolic Metabolic pathways eco01100 Specdb::CMs 13457 Specdb::CMs 32136 Specdb::CMs 37554 Specdb::NmrOneD 1385 Specdb::MsMs 686 Specdb::MsMs 687 Specdb::MsMs 688 Specdb::MsMs 295651 Specdb::MsMs 295652 Specdb::MsMs 295653 Specdb::MsMs 336712 Specdb::MsMs 336713 Specdb::MsMs 336714 Specdb::MsMs 440119 Specdb::MsMs 445332 Specdb::MsMs 445333 Specdb::MsMs 445334 Specdb::MsMs 445335 Specdb::MsMs 451955 Specdb::NmrTwoD 1329 C01021 Aromatic amino acid + alpha-Ketoglutarate <> Aromatic oxo acid + L-Glutamate R03120