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Record Information
Version	2.0
Creation Date	2012-05-31 14:52:44 -0600
Update Date	2015-06-03 17:20:22 -0600
Secondary Accession Numbers	ECMDB20599
Identification
Name:	Phenylhydantoin
Description	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.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa9560dac> Close
Synonyms:	5-Phenyl-(.+-.)-2,4-Imidazolidinedione 5-Phenyl-2,4-Imidazolidinedione 5-Phenyl-Hydantoin 5-Phenylhydantoin Hydantoin, 5-phenyl- (8CI)
Chemical Formula:	C9H8N2O2
Weight:	Average: 176.172 Monoisotopic: 176.05857751
InChI Key:	NXQJDVBMMRCKQG-UHFFFAOYSA-N
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)
CAS number:	89-24-7
IUPAC Name:	4-phenyl-4H-imidazole-2,5-diol
Traditional IUPAC Name:	5-phenyl-5H-imidazole-2,4-diol
SMILES:	OC1=NC(C(O)=N1)C1=CC=CC=C1
Chemical Taxonomy
Description	belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Azolidines
Sub Class	Imidazolidines
Direct Parent	Phenylhydantoins
Alternative Parents	Phenylimidazolidines Alpha amino acids and derivatives 5-monosubstituted hydantoins N-acyl ureas Benzene and substituted derivatives Dicarboximides Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	5-phenylhydantoin Phenylimidazolidine Alpha-amino acid or derivatives 5-monosubstituted hydantoin N-acyl urea Ureide Monocyclic benzene moiety Benzenoid Dicarboximide Urea Carbonic acid derivative Carboxylic acid derivative Azacycle Hydrocarbon derivative Organic oxide Organooxygen compound Organonitrogen compound Organopnictogen compound Organic nitrogen compound Carbonyl group Organic oxygen compound Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	a small molecule (PHENYLHYDANTOIN )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.53 g/L ALOGPS logP 0.62 ALOGPS logP 1.74 ChemAxon logS -2.5 ALOGPS pKa (Strongest Acidic) 4.52 ChemAxon pKa (Strongest Basic) 0.033 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 65.18 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 46.45 m³·mol⁻¹ ChemAxon Polarizability 17.17 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Phenylhydantoin + Water <> corresponding carbamoyl amino acid Phenylhydantoin + Water <> phenylureidoacetic acid
SMPDB Pathways:	Collection of Reactions without pathways PW001891
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-001i-2900000000-29031da4f3df492b09a7 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0900000000-b8ee69b6ad9468557700 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0zi0-0900000000-2608f617a5a27f1e6151 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0zfr-6900000000-0c826d2a1ec8a246a52d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-2900000000-2fd3b420a7b79ffe7263 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-002f-9700000000-5ba49553bdd1e846ac2d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0f6x-9500000000-396218cd005d46fe3c61 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0900000000-72b2beb77ff784d05490 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0ugi-2900000000-0c30a9d25db568f80182 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udi-4900000000-accbe98700d8ea46df6e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4i-0900000000-ca891ec865f0b18f774e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-054o-9700000000-2b7dcd52fe2a35e704b3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9300000000-2eec2b1f43ac2ef28d16 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 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. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID HMDB0246838 Pubchem Compound ID 1002 Kegg ID Not Available ChemSpider ID 977 Wikipedia ID Not Available BioCyc ID PHENYLHYDANTOIN EcoCyc ID PHENYLHYDANTOIN

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