2.02012-05-31 13:52:45 -06002015-06-03 15:54:07 -0600ECMDB01439M2MDB000388Phosphoribosyl formamidocarboxamidePhosphoribosyl 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 carboxamide5'-p-Ribosyl-5-formamido-4-imidazolecarboxamide5'-Phosphoribosyl-5-formamido-4-imidazole carboxamide5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide5-Formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide5-Formamido-1-(5-phosphoribosyl)-imidazole-4-carboxamide5-Formylamidoimidazole-4-carboxamide ribonucleotide5-Phosphoribosyl-5-formamido-4-imid-carboxamideFAICARPhosphoribosyl-formamido-carboxamideC10H15N4O9P366.2213366.05766461{[(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 acidNC(=O)C1=C(NC=O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1OInChI=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/s1ABCOOORLYAOBOZ-KQYNXXCUSA-NSolidCytosolCytosollogp-1.83logs-2.23solubility2.14e+00 g/llogp-4.1pka_strongest_acidic1.21pka_strongest_basic6.25iupac{[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamido-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acidaverage_mass366.2213mono_mass366.05766461smilesNC(=O)C1=C(NC=O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1OformulaC10H15N4O9PinchiInChI=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/s1inchikeyABCOOORLYAOBOZ-KQYNXXCUSA-Npolar_surface_area206.46refractivity74.81polarizability30.52rotatable_bond_count6acceptor_count9donor_count6physiological_charge-2formal_charge0Purine metabolismec00230One carbon pool by folateDihydrofolic 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.
PW000773ec00670MetabolicMetabolic pathwayseco01100inosine-5'-phosphate biosynthesis IPWY-6123Specdb::CMs13626Specdb::CMs38074Specdb::CMs132938Specdb::CMs140672Specdb::NmrOneD96098Specdb::NmrOneD96099Specdb::NmrOneD96100Specdb::NmrOneD96101Specdb::NmrOneD96102Specdb::NmrOneD96103Specdb::NmrOneD96104Specdb::NmrOneD96105Specdb::NmrOneD96106Specdb::NmrOneD96107Specdb::NmrOneD96108Specdb::NmrOneD96109Specdb::NmrOneD96110Specdb::NmrOneD96111Specdb::NmrOneD96112Specdb::NmrOneD96113Specdb::NmrOneD96114Specdb::NmrOneD96115Specdb::NmrOneD96116Specdb::NmrOneD96117Specdb::MsMs27839Specdb::MsMs27840Specdb::MsMs27841Specdb::MsMs34397Specdb::MsMs34398Specdb::MsMs34399Specdb::MsMs2354284Specdb::MsMs2354285Specdb::MsMs2354286Specdb::MsMs2607372Specdb::MsMs2607373Specdb::MsMs2607374HMDB014391011145893C0473418381PHOSPHORIBOSYL-FORMAMIDO-CARBOXAMIDEFAIKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Adenylosuccinate lyaseP0AB89PUR8_ECOLIpurBhttp://ecmdb.ca/proteins/P0AB89.xmlBifunctional purine biosynthesis protein purHP15639PUR9_ECOLIpurHhttp://ecmdb.ca/proteins/P15639.xmlImidazole glycerol phosphate synthase subunit hisHP60595HIS5_ECOLIhisHhttp://ecmdb.ca/proteins/P60595.xmlImidazole glycerol phosphate synthase subunit hisFP60664HIS6_ECOLIhisFhttp://ecmdb.ca/proteins/P60664.xmlL-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ionSAICAR <> Phosphoribosyl formamidocarboxamide + Fumaric acidWater + Inosinic acid <> Phosphoribosyl formamidocarboxamideR01127IMPCYCLOHYDROLASE-RXNN10-Formyl-THF + Phosphoribosyl formamidocarboxamide <> Phosphoribosyl formamidocarboxamide + Tetrahydrofolic acidN10-Formyl-THF + Phosphoribosyl formamidocarboxamide <> Phosphoribosyl formamidocarboxamide + Tetrahydrofolic acidN10-Formyl-THF + AICAR <> Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamideR04560N10-Formyl-THF + AICAR > Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamideR04560AICARTRANSFORM-RXNInosinic acid + Water > Phosphoribosyl formamidocarboxamideWater + Inosinic acid <> Phosphoribosyl formamidocarboxamideN10-Formyl-THF + AICAR <> Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamideWater + Inosinic acid <> Phosphoribosyl formamidocarboxamide