2.02012-05-31 14:52:44 -06002015-06-03 17:20:22 -0600ECMDB20599M2MDB001399PhenylhydantoinPhenylhydantoin is a cyclic ureide and it is believed that E. coli may use these compounds as nutrient sources. The gene hyuA codes for d-stereospecific phenylhydantoinase (465 amino acids) which is a homotetramer. This enzyme belongs to the cyclic amidohydrolase superfamily. E. coli D-phenylhydantoinase exhibits a distinct activity toward phenylhydantoin with an aromatic side chain at the 5' position but does not readily hydrolyze the simple cyclic ureides. D-phenylhydantoinase shares a significant homology (>45%) with those of allantoinase and dihydropyrimidinase.5-Phenyl-(.+-.)-2,4-Imidazolidinedione5-Phenyl-2,4-Imidazolidinedione5-Phenyl-Hydantoin5-PhenylhydantoinHydantoin, 5-phenyl- (8CI)C9H8N2O2176.172176.058577514-phenyl-4H-imidazole-2,5-diol5-phenyl-5H-imidazole-2,4-diol89-24-7OC1=NC(C(O)=N1)C1=CC=CC=C1InChI=1S/C9H8N2O2/c12-8-7(10-9(13)11-8)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12,13)NXQJDVBMMRCKQG-UHFFFAOYSA-NOuter membraneInner membranelogp0.62logs-2.52solubility5.33e-01 g/llogp1.74pka_strongest_acidic4.52pka_strongest_basic0.033iupac4-phenyl-4H-imidazole-2,5-diolaverage_mass176.172mono_mass176.05857751smilesOC1=NC(C(O)=N1)C1=CC=CC=C1formulaC9H8N2O2inchiInChI=1S/C9H8N2O2/c12-8-7(10-9(13)11-8)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12,13)inchikeyNXQJDVBMMRCKQG-UHFFFAOYSA-Npolar_surface_area65.18refractivity46.45polarizability17.17rotatable_bond_count1acceptor_count4donor_count2physiological_charge-1formal_charge0Collection of Reactions without pathwaysPW001891MetabolicSpecdb::CMs106870Specdb::CMs119141Specdb::CMs825526Specdb::CMs825527Specdb::CMs825528Specdb::CMs825529Specdb::CMs825530Specdb::CMs825531Specdb::NmrOneD258348Specdb::NmrOneD258349Specdb::NmrOneD258350Specdb::NmrOneD258351Specdb::NmrOneD258352Specdb::NmrOneD258353Specdb::NmrOneD258354Specdb::NmrOneD258355Specdb::NmrOneD258356Specdb::NmrOneD258357Specdb::NmrOneD258358Specdb::NmrOneD258359Specdb::NmrOneD258360Specdb::NmrOneD258361Specdb::NmrOneD258362Specdb::NmrOneD258363Specdb::NmrOneD258364Specdb::NmrOneD258365Specdb::NmrOneD258366Specdb::NmrOneD258367Specdb::MsMs26843Specdb::MsMs26844Specdb::MsMs26845Specdb::MsMs33401Specdb::MsMs33402Specdb::MsMs33403Specdb::MsMs3407971Specdb::MsMs3407972Specdb::MsMs3407973Specdb::MsMs3407974Specdb::MsMs3407975Specdb::MsMs34079761002977PHENYLHYDANTOINKeseler, 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-D590.21097882Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064D-phenylhydantoinaseQ46806PHYDA_ECOLIhyuAhttp://ecmdb.ca/proteins/Q46806.xmlPhenylhydantoin + Water <> corresponding carbamoyl amino acidRXN0-275Phenylhydantoin + Water <> phenylureidoacetic acidPW_R005870