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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:58:54 UTC
Update Date2019-07-23 07:14:14 UTC
HMDB IDHMDB0060389
Secondary Accession Numbers
  • HMDB60389
Metabolite Identification
Common Name4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one
Description4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one, also known as 4-OH-5-PH-O or CCMF CPD, 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. 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one exists in all living organisms, ranging from bacteria to humans. 4-hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one can be converted into 5-phenyl-1,3-oxazinane-2,4-dione through the action of the enzyme alcohol dehydrogenase 1A. In humans, 4-hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one 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. 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one 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?1563866054
Synonyms
ValueSource
4-OH-5-PH-OHMDB
CCMF CPDHMDB
4-Hydroxy-5-phenyl-1,3-oxazaperhydroin-2-oneHMDB
Chemical FormulaC10H11NO3
Average Molecular Weight193.1992
Monoisotopic Molecular Weight193.073893223
IUPAC Name5-phenyl-5,6-dihydro-4H-1,3-oxazine-2,4-diol
Traditional Name5-phenyl-5,6-dihydro-4H-1,3-oxazine-2,4-diol
CAS Registry NumberNot Available
SMILES
OC1N=C(O)OCC1C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H11NO3/c12-9-8(6-14-10(13)11-9)7-4-2-1-3-5-7/h1-5,8-9,12H,6H2,(H,11,13)
InChI KeyXZZMJRBYVRSAOS-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
  • Carbamic acid ester
  • Carbonic acid derivative
  • Alkanolamine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.81 g/LALOGPS
logP0.4ALOGPS
logP1.84ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)7.92ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.05 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.01 m³·mol⁻¹ChemAxon
Polarizability19.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-3900000000-5e80893a8f38061556beSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9542000000-a19beedc712ddd931126Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000y-0900000000-2871d3961ae9c47cd1b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-e4e096245a0bfe98e77dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ugi-5900000000-fcd193c908acbd29a137Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-699a6ff79dbdb21101beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-2900000000-5c875b74d8517b7514a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-360cc92224d8b9fdb337Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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 IDC16595
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound21350392
      PDB IDNot Available
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH 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