Record Information
Version2.0
Creation Date2012-08-09 09:25:23 -0600
Update Date2015-06-03 17:21:44 -0600
Secondary Accession Numbers
  • ECMDB21541
Identification
Name:Hydroxyphenylhydantoin
DescriptionHydroxyphenylhydantoin is a member of the chemical class known as Ureides. These are compounds containing an ureide group with the general structure R-CO-NH-CO-N(R)R'', formally derived by the acylation of urea. Hydroxyphenylhydantoin is a substrate that is processed by D-phenylhydantoinase (HyuA gene) (in vitro).
Structure
Thumb
Synonyms:
  • 5-(4-Hydroxyphenyl)-2,4-imidazolidinedione, 5-(4-hydroxyphenyl)imidazolidine-2,4-dione
  • 5-(p-Hydroxyphenyl)hydantoin
Chemical Formula:C9H8N2O3
Weight:Average: 192.1714
Monoisotopic: 192.053492132
InChI Key:IEUWJBJXAOXHGF-UHFFFAOYSA-N
InChI:InChI=1S/C9H8N2O3/c12-8-6-10(9(13)11(8)14)7-4-2-1-3-5-7/h1-5,14H,6H2
CAS number:Not Available
IUPAC Name:3-hydroxy-1-phenylimidazolidine-2,4-dione
Traditional IUPAC Name:3-hydroxy-1-phenylimidazolidine-2,4-dione
SMILES:ON1C(=O)CN(C1=O)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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentPhenylhydantoins
Alternative Parents
Substituents
  • 1-phenylhydantoin
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboximide
  • Carbonic acid derivative
  • Hydroxamic acid
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.02 g/LALOGPS
logP0.04ALOGPS
logP0.43ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.12ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.85 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.48 m³·mol⁻¹ChemAxon
Polarizability18.06 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-b3a4534bf25d462ed701View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-44ef9878073063b4418fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-5900000000-e091746e83c715b365c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-0befb7df262e4ac9b595View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9400000000-290c0e0731a1b5d596e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-da179b28137e102439baView in MoNA
References
References:
  • 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
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID53429923
Kegg IDNot Available
ChemSpider ID26559222
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in cyclic amides
Specific function:
Catalyzes the stereospecific hydrolysis of the cyclic amide bond of D-hydantoin derivatives with an aromatic side chains at the 5'-position. Has no activity on dihydropyrimidines. The physiological function is unknown
Gene Name:
hyuA
Uniprot ID:
Q46806
Molecular weight:
51025