2.0 2012-05-31 13:52:45 -0600 2015-06-03 15:54:07 -0600 ECMDB01439 M2MDB000388 Phosphoribosyl formamidocarboxamide Phosphoribosyl formamidocarboxamide is an intermediate in purine metabolism, where it is the byproduct of phosphoribosylaminoimidazolecarboxamide formyltransferase (EC 2.1.2.3) and IMP cyclohydrolase (EC 3.5.4.10). It is also a byproduct of Ligases (EC 6.3.4.-). 5'-p-Ribosyl-5-formamido-4-imidazole carboxamide 5'-p-Ribosyl-5-formamido-4-imidazolecarboxamide 5'-Phosphoribosyl-5-formamido-4-imidazole carboxamide 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide 5-Formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide 5-Formamido-1-(5-phosphoribosyl)-imidazole-4-carboxamide 5-Formylamidoimidazole-4-carboxamide ribonucleotide 5-Phosphoribosyl-5-formamido-4-imid-carboxamide FAICAR Phosphoribosyl-formamido-carboxamide C10H15N4O9P 366.2213 366.05766461 {[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamido-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid [(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamidoimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid NC(=O)C1=C(NC=O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O InChI=1S/C10H15N4O9P/c11-8(18)5-9(13-3-15)14(2-12-5)10-7(17)6(16)4(23-10)1-22-24(19,20)21/h2-4,6-7,10,16-17H,1H2,(H2,11,18)(H,13,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1 ABCOOORLYAOBOZ-KQYNXXCUSA-N Solid Cytosol Cytosol logp -1.83 ALOGPS logs -2.23 ALOGPS solubility 2.14e+00 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 1.21 ChemAxon pka_strongest_basic 6.25 ChemAxon iupac {[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamido-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 366.2213 ChemAxon mono_mass 366.05766461 ChemAxon smiles NC(=O)C1=C(NC=O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O ChemAxon formula C10H15N4O9P ChemAxon inchi InChI=1S/C10H15N4O9P/c11-8(18)5-9(13-3-15)14(2-12-5)10-7(17)6(16)4(23-10)1-22-24(19,20)21/h2-4,6-7,10,16-17H,1H2,(H2,11,18)(H,13,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1 ChemAxon inchikey ABCOOORLYAOBOZ-KQYNXXCUSA-N ChemAxon polar_surface_area 206.46 ChemAxon refractivity 74.81 ChemAxon polarizability 30.52 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 One carbon pool by folate Dihydrofolic acid, a product of the folate biosynthesis pathway, can be metabolized by multiple enzymes. Dihydrofolic acid can be reduced by a NADP-driven dihydrofolate reductase resulting in a NADPH, hydrogen ion and folic acid. Dihydrofolic acid can also be reduced by an NADPH-driven dihydrofolate reductase resulting in a NADP and a tetrahydrofolic acid. Folic acid can also produce a tetrahydrofolic acid through a NADPH-driven dihydrofolate reductase. Dihydrofolic acid also interacts with 5-thymidylic acid through a thymidylate synthase resulting in the release of dUMP and 5,10-methylene-THF Tetrahydrofolic acid can be converted into 5,10-methylene-THF through two different reversible reactions. Tetrahydrofolic acid interacts with a S-Aminomethyldihydrolipoylprotein through a aminomethyltransferase resulting in the release of ammonia, a dihydrolipoylprotein and 5,10-Methylene-THF Tetrahydrofolic acid interacts with L-serine through a glycine hydroxymethyltransferase resulting in a glycine, water and 5,10-Methylene-THF. The compound 5,10-methylene-THF reacts with an NADPH dependent methylenetetrahydrofolate reductase [NAD(P)H] resulting in NADP and 5-Methyltetrahydrofolic acid. This compound interacts with homocysteine through a methionine synthase resulting in L-methionine and tetrahydrofolic acid. Tetrahydrofolic acid can be metabolized into 10-formyltetrahydrofolate through 4 different enzymes: 1.- Tetrahydrofolic acid interacts with FAICAR through a phosphoribosylaminoimidazolecarboxamide formyltransferase resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide and a 10-formyltetrahydrofolate 2.-Tetrahydrofolic acid interacts with 5'-Phosphoribosyl-N-formylglycinamide through a phosphoribosylglycinamide formyltransferase 2 resulting in a Glycineamideribotide and a 10-formyltetrahydrofolate 3.-Tetrahydrofolic acid interacts with Formic acid through a formyltetrahydrofolate hydrolase resulting in water and a 10-formyltetrahydrofolate 4.-Tetrahydrofolic acid interacts with N-formylmethionyl-tRNA(fMet) through a 10-formyltetrahydrofolate:L-methionyl-tRNA(fMet) N-formyltransferase resulting in a L-methionyl-tRNA(Met) and a 10-formyltetrahydrofolate 10-formyltetrahydrofolate can interact with a hydrogen ion through a bifunctional 5,10-methylene-tetrahydrofolate dehydrogenase resulting in water and 5,10-methenyltetrahydrofolic acid. Tetrahydrofolic acid can be metabolized into 5,10-methenyltetrahydrofolic acid by reacting with a 5'-phosphoribosyl-a-N-formylglycineamidine through a phosphoribosylglycinamide formyltransferase 2 resulting in water, glycineamideribotide and 5,10-methenyltetrahydrofolic acid. The latter compound can either interact with water through an aminomethyltransferase resulting in a N5-Formyl-THF, or it can interact with a NADPH driven bifunctional 5,10-methylene-tetrahydrofolate dehydrogenase resulting in a NADP and 5,10-Methylene THF. PW000773 ec00670 Metabolic Metabolic pathways eco01100 inosine-5'-phosphate biosynthesis I PWY-6123 Specdb::CMs 13626 Specdb::CMs 38074 Specdb::CMs 132938 Specdb::CMs 140672 Specdb::NmrOneD 96098 Specdb::NmrOneD 96099 Specdb::NmrOneD 96100 Specdb::NmrOneD 96101 Specdb::NmrOneD 96102 Specdb::NmrOneD 96103 Specdb::NmrOneD 96104 Specdb::NmrOneD 96105 Specdb::NmrOneD 96106 Specdb::NmrOneD 96107 Specdb::NmrOneD 96108 Specdb::NmrOneD 96109 Specdb::NmrOneD 96110 Specdb::NmrOneD 96111 Specdb::NmrOneD 96112 Specdb::NmrOneD 96113 Specdb::NmrOneD 96114 Specdb::NmrOneD 96115 Specdb::NmrOneD 96116 Specdb::NmrOneD 96117 Specdb::MsMs 27839 Specdb::MsMs 27840 Specdb::MsMs 27841 Specdb::MsMs 34397 Specdb::MsMs 34398 Specdb::MsMs 34399 Specdb::MsMs 2354284 Specdb::MsMs 2354285 Specdb::MsMs 2354286 Specdb::MsMs 2607372 Specdb::MsMs 2607373 Specdb::MsMs 2607374 HMDB01439 1011 145893 C04734 18381 PHOSPHORIBOSYL-FORMAMIDO-CARBOXAMIDE FAI 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 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Adenylosuccinate lyase P0AB89 PUR8_ECOLI purB http://ecmdb.ca/proteins/P0AB89.xml Bifunctional purine biosynthesis protein purH P15639 PUR9_ECOLI purH http://ecmdb.ca/proteins/P15639.xml Imidazole glycerol phosphate synthase subunit hisH P60595 HIS5_ECOLI hisH http://ecmdb.ca/proteins/P60595.xml Imidazole glycerol phosphate synthase subunit hisF P60664 HIS6_ECOLI hisF http://ecmdb.ca/proteins/P60664.xml L-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ion SAICAR <> Phosphoribosyl formamidocarboxamide + Fumaric acid Water + Inosinic acid <> Phosphoribosyl formamidocarboxamide R01127 IMPCYCLOHYDROLASE-RXN N10-Formyl-THF + Phosphoribosyl formamidocarboxamide <> Phosphoribosyl formamidocarboxamide + Tetrahydrofolic acid N10-Formyl-THF + Phosphoribosyl formamidocarboxamide <> Phosphoribosyl formamidocarboxamide + Tetrahydrofolic acid N10-Formyl-THF + AICAR <> Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide R04560 N10-Formyl-THF + AICAR > Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide R04560 AICARTRANSFORM-RXN Inosinic acid + Water > Phosphoribosyl formamidocarboxamide Water + Inosinic acid <> Phosphoribosyl formamidocarboxamide N10-Formyl-THF + AICAR <> Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide Water + Inosinic acid <> Phosphoribosyl formamidocarboxamide