2.0 2012-07-30 14:54:47 -0600 2015-06-03 17:20:49 -0600 ECMDB21180 M2MDB001589 6-Carboxy-5,6,7,8-tetrahydropterin 6-carboxy-5,6,7,8-tetrahydropterin is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).6-carboxy-5,6,7,8-tetrahydropterin is catalyzed by QueD. Escherichia coli QueD is a 6-carboxy-5,6,7,8-tetrahydropterin synthase. (PMID 19231875) 2-Amino-4-oxo-3,4,5,6,7,8-hexahydropteridine-6-carboxylate 2-Amino-4-oxo-3,4,5,6,7,8-hexahydropteridine-6-carboxylic acid 5,6,7,8-Tetrahydropterin-6-carboxylate anion 5,6,7,8-Tetrahydropterin-6-carboxylate(1) 5,6,7,8-Tetrahydropterin-6-carboxylic acid anion 5,6,7,8-Tetrahydropterin-6-carboxylic acid(1) 6-Carboxy-5,6,7,8-tetrahydropterin 6-Carboxylato-5,6,7,8-tetrahydropterin 6-Carboxylato-5,6,7,8-tetrahydropterin anion 6-Carboxylato-5,6,7,8-tetrahydropterin(1) 6-Carboxytetrahydropterin C7H9N5O3 211.1781 211.070539179 2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridine-6-carboxylic acid 2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridine-6-carboxylic acid NC1=NC2=C(NC(CN2)C(O)=O)C(=O)N1 InChI=1S/C7H9N5O3/c8-7-11-4-3(5(13)12-7)10-2(1-9-4)6(14)15/h2,10H,1H2,(H,14,15)(H4,8,9,11,12,13) QSIYONWVWDSRRO-UHFFFAOYSA-N Cytosol logp -1.87 ALOGPS logs -2.24 ALOGPS solubility 1.21e+00 g/l ALOGPS logp -3 ChemAxon pka_strongest_acidic 3.67 ChemAxon pka_strongest_basic 4.84 ChemAxon iupac 2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridine-6-carboxylic acid ChemAxon average_mass 211.1781 ChemAxon mono_mass 211.070539179 ChemAxon smiles NC1=NC2=C(NC(CN2)C(O)=O)C(=O)N1 ChemAxon formula C7H9N5O3 ChemAxon inchi InChI=1S/C7H9N5O3/c8-7-11-4-3(5(13)12-7)10-2(1-9-4)6(14)15/h2,10H,1H2,(H,14,15)(H4,8,9,11,12,13) ChemAxon inchikey QSIYONWVWDSRRO-UHFFFAOYSA-N ChemAxon polar_surface_area 128.84 ChemAxon refractivity 58.12 ChemAxon polarizability 19 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Folate biosynthesis The biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate. Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid. (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate. This product goes on to a one carbon pool by folate pathway. PW000908 ec00790 Metabolic Metabolic pathways eco01100 preQ0 metabolism PreQ0 or 7-cyano-7-carbaguanine is biosynthesized by degrading GTP. GTP first interacts with water through a GTP cyclohydrolase resulting in the release of a formate, a hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound then interacts with water through a 6-carboxy-5,6,7,8-tetrahydropterin synthase resulting in a acetaldehyde, triphosphate, 2 hydrogen ion and 6-carboxy-5,6,7,8-tetrahydropterin. The latter compound then reacts spontaneously with a hydrogen ion resulting in the release of a ammonium molecule and a 7-carboxy-7-deazaguanine. This compound then interacts with ATP and ammonium through 7-cyano-7-deazaguanine synthase resulting in the release of water, phosphate, ADP, hydrogen ion and a 7-cyano-7-carbaguanine. The degradation of 7-cyano-7-deazaguanine can lead to produce a preQ1 or a queuine by reacting with 3 hydrogen ions and 2 NADPH through a 7-cyano-7-deazaguanine reductase. PreQ1 then interacts with a guanine 34 in tRNA through a tRNA-guanine transglycosylase resulting in a release of a guanine and a 7-aminomethyl-7-deazaguanosine 34 in tRNA. This nucleic acid then interacts with SAM through a S-adenosylmethionine tRNA ribosyltransferase-isomerase resulting in a release of a hydrogen ion, L-methionine, adenine and an epoxyqueuosine PW001893 Metabolic preQ₀ biosynthesis PWY-6703 Specdb::CMs 37160 Specdb::CMs 48190 Specdb::CMs 173525 Specdb::NmrOneD 58092 Specdb::NmrOneD 58093 Specdb::NmrOneD 58094 Specdb::NmrOneD 58095 Specdb::NmrOneD 58096 Specdb::NmrOneD 58097 Specdb::NmrOneD 58098 Specdb::NmrOneD 58099 Specdb::NmrOneD 58100 Specdb::NmrOneD 58101 Specdb::NmrOneD 58102 Specdb::NmrOneD 58103 Specdb::NmrOneD 58104 Specdb::NmrOneD 58105 Specdb::NmrOneD 58106 Specdb::NmrOneD 58107 Specdb::NmrOneD 58108 Specdb::NmrOneD 58109 Specdb::NmrOneD 58110 Specdb::NmrOneD 58111 Specdb::MsMs 24839 Specdb::MsMs 24840 Specdb::MsMs 24841 Specdb::MsMs 31397 Specdb::MsMs 31398 Specdb::MsMs 31399 44123380 26332086 C20239 61032 CPD0-1699 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 6-carboxy-5,6,7,8-tetrahydropterin synthase P65870 QUED_ECOLI queD http://ecmdb.ca/proteins/P65870.xml 7-carboxy-7-deazaguanine synthase; queosine biosynthesis P64554 queE http://ecmdb.ca/proteins/P64554.xml Dihydroneopterin triphosphate + Water > Acetaldehyde + 6-Carboxy-5,6,7,8-tetrahydropterin + Hydrogen ion + Triphosphate RXN0-5507 6-Carboxy-5,6,7,8-tetrahydropterin <> 7-Carboxy-7-carbaguanine + Ammonia + 7-Deaza-7-carboxyguanine R10002 6-Carboxy-5,6,7,8-tetrahydropterin + S-Adenosylmethionine + Hydrogen ion > 7-carboxy-7-deazaguanine + 5'-Deoxyadenosine + L-Methionine + Ammonia RXN0-6575 Dihydroneopterin triphosphate + Water > 6-Carboxy-5,6,7,8-tetrahydropterin + Acetaldehyde + Triphosphate 6-Carboxy-5,6,7,8-tetrahydropterin > 7-Deaza-7-carboxyguanine + Ammonia 7,8-dihydroneopterin 3'-triphosphate + Water > Acetaldehyde + Triphosphate +2 Hydrogen ion + 6-Carboxy-5,6,7,8-tetrahydropterin + Triphosphate PW_R005178