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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:59:47 UTC
Update Date2021-09-14 15:47:40 UTC
HMDB IDHMDB0060400
Secondary Accession Numbers
  • HMDB60400
Metabolite Identification
Common Name5-Phenyl-1,3-oxazinane-2,4-dione
Description5-Phenyl-1,3-oxazinane-2,4-dione, also known as 5-phenyl-oxzd, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 5-Phenyl-1,3-oxazinane-2,4-dione is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Phenyl-1,3-oxazinane-2,4-dione exists in all living organisms, ranging from bacteria to humans. 5-phenyl-1,3-oxazinane-2,4-dione can be biosynthesized from 4-hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one; which is mediated by the enzyme alcohol dehydrogenase 1A. In humans, 5-phenyl-1,3-oxazinane-2,4-dione is involved in felbamate metabolism pathway. It is used to treat partial seizures (with and without generalization) in adults and partial and generalized seizures associated with Lennox-Gastaut syndrome in children. Felbamate (marketed under the brand name Felbatol by MedPointe) is an anti-epileptic drug used in the treatment of epilepsy. 5-Phenyl-1,3-oxazinane-2,4-dione is a metabolite of felbamate. However, an increased risk of potentially fatal aplastic anemia and/or liver failure limit the drugs usage to severe refractory epilepsy.
Structure
Data?1563866055
Synonyms
ValueSource
5-Phenyl-oxzdHMDB
Chemical FormulaC10H9NO3
Average Molecular Weight191.1834
Monoisotopic Molecular Weight191.058243159
IUPAC Name4-hydroxy-5-phenyl-5,6-dihydro-2H-1,3-oxazin-2-one
Traditional Name4-hydroxy-5-phenyl-5,6-dihydro-1,3-oxazin-2-one
CAS Registry NumberNot Available
SMILES
OC1=NC(=O)OCC1C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H9NO3/c12-9-8(6-14-10(13)11-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,12,13)
InChI KeyYPIQXPKZXKWWSZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • 1,3-oxazinane
  • Monocyclic benzene moiety
  • Oxazinane
  • Dicarboximide
  • Carbamic acid ester
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP10(1.19) g/LALOGPS
logP10(1.56) g/LChemAxon
logS10(-2.6) g/LALOGPS
pKa (Strongest Acidic)6.25ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.89 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.79 m³·mol⁻¹ChemAxon
Polarizability18.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.6631661259
DarkChem[M-H]-140.56531661259
DeepCCS[M+H]+136.14930932474
DeepCCS[M-H]-133.53930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Phenyl-1,3-oxazinane-2,4-dioneOC1=NC(=O)OCC1C1=CC=CC=C13022.8Standard polar33892256
5-Phenyl-1,3-oxazinane-2,4-dioneOC1=NC(=O)OCC1C1=CC=CC=C11877.5Standard non polar33892256
5-Phenyl-1,3-oxazinane-2,4-dioneOC1=NC(=O)OCC1C1=CC=CC=C11955.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Phenyl-1,3-oxazinane-2,4-dione,1TMS,isomer #1C[Si](C)(C)OC1=NC(=O)OCC1C1=CC=CC=C11850.1Semi standard non polar33892256
5-Phenyl-1,3-oxazinane-2,4-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(=O)OCC1C1=CC=CC=C12059.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phenyl-1,3-oxazinane-2,4-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-7900000000-5d278c88e45e375325c72017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phenyl-1,3-oxazinane-2,4-dione GC-MS (1 TMS) - 70eV, Positivesplash10-0f6x-9720000000-71a378ec4edf16eeb59f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phenyl-1,3-oxazinane-2,4-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phenyl-1,3-oxazinane-2,4-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenyl-1,3-oxazinane-2,4-dione 10V, Positive-QTOFsplash10-0006-0900000000-8a1b4b15aa4986cc19a22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenyl-1,3-oxazinane-2,4-dione 20V, Positive-QTOFsplash10-0006-0900000000-bbcbc7de8308513d1fa22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenyl-1,3-oxazinane-2,4-dione 40V, Positive-QTOFsplash10-0ufu-9700000000-a25c0f8a2b9a722b169b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenyl-1,3-oxazinane-2,4-dione 10V, Negative-QTOFsplash10-0005-0900000000-1bf03af330e48c6283bd2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenyl-1,3-oxazinane-2,4-dione 20V, Negative-QTOFsplash10-0006-1900000000-7721f5ba3311d43324682015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenyl-1,3-oxazinane-2,4-dione 40V, Negative-QTOFsplash10-0006-9200000000-7de3050a4ce64112c5142015-09-15Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16596
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21350393
PDB IDNot Available
ChEBI ID80594
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular weight:
40221.335
Reactions
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one + NAD → 5-Phenyl-1,3-oxazinane-2,4-dione + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
Reactions
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one + NAD → 5-Phenyl-1,3-oxazinane-2,4-dione + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
Reactions
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one + NAD → 5-Phenyl-1,3-oxazinane-2,4-dione + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular weight:
41480.985
Reactions
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one + NAD → 5-Phenyl-1,3-oxazinane-2,4-dione + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37
Reactions
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one + NAD → 5-Phenyl-1,3-oxazinane-2,4-dione + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular weight:
39072.275
Reactions
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one + NAD → 5-Phenyl-1,3-oxazinane-2,4-dione + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular weight:
39867.27
Reactions
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one + NAD → 5-Phenyl-1,3-oxazinane-2,4-dione + NADH + Hydrogen Iondetails