2.0 2012-05-31 14:52:44 -0600 2015-06-03 17:20:22 -0600 ECMDB20599 M2MDB001399 Phenylhydantoin Phenylhydantoin 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-Imidazolidinedione 5-Phenyl-2,4-Imidazolidinedione 5-Phenyl-Hydantoin 5-Phenylhydantoin Hydantoin, 5-phenyl- (8CI) C9H8N2O2 176.172 176.05857751 4-phenyl-4H-imidazole-2,5-diol 5-phenyl-5H-imidazole-2,4-diol 89-24-7 OC1=NC(C(O)=N1)C1=CC=CC=C1 InChI=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-N Outer membrane Inner membrane logp 0.62 ALOGPS logs -2.52 ALOGPS solubility 5.33e-01 g/l ALOGPS logp 1.74 ChemAxon pka_strongest_acidic 4.52 ChemAxon pka_strongest_basic 0.033 ChemAxon iupac 4-phenyl-4H-imidazole-2,5-diol ChemAxon average_mass 176.172 ChemAxon mono_mass 176.05857751 ChemAxon smiles OC1=NC(C(O)=N1)C1=CC=CC=C1 ChemAxon formula C9H8N2O2 ChemAxon inchi InChI=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) ChemAxon inchikey NXQJDVBMMRCKQG-UHFFFAOYSA-N ChemAxon polar_surface_area 65.18 ChemAxon refractivity 46.45 ChemAxon polarizability 17.17 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Collection of Reactions without pathways PW001891 Metabolic Specdb::CMs 106870 Specdb::CMs 119141 Specdb::CMs 825526 Specdb::CMs 825527 Specdb::CMs 825528 Specdb::CMs 825529 Specdb::CMs 825530 Specdb::CMs 825531 Specdb::NmrOneD 258348 Specdb::NmrOneD 258349 Specdb::NmrOneD 258350 Specdb::NmrOneD 258351 Specdb::NmrOneD 258352 Specdb::NmrOneD 258353 Specdb::NmrOneD 258354 Specdb::NmrOneD 258355 Specdb::NmrOneD 258356 Specdb::NmrOneD 258357 Specdb::NmrOneD 258358 Specdb::NmrOneD 258359 Specdb::NmrOneD 258360 Specdb::NmrOneD 258361 Specdb::NmrOneD 258362 Specdb::NmrOneD 258363 Specdb::NmrOneD 258364 Specdb::NmrOneD 258365 Specdb::NmrOneD 258366 Specdb::NmrOneD 258367 Specdb::MsMs 26843 Specdb::MsMs 26844 Specdb::MsMs 26845 Specdb::MsMs 33401 Specdb::MsMs 33402 Specdb::MsMs 33403 Specdb::MsMs 3407971 Specdb::MsMs 3407972 Specdb::MsMs 3407973 Specdb::MsMs 3407974 Specdb::MsMs 3407975 Specdb::MsMs 3407976 1002 977 PHENYLHYDANTOIN 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 Winder, 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. 18331064 D-phenylhydantoinase Q46806 PHYDA_ECOLI hyuA http://ecmdb.ca/proteins/Q46806.xml Phenylhydantoin + Water <> corresponding carbamoyl amino acid RXN0-275 Phenylhydantoin + Water <> phenylureidoacetic acid PW_R005870