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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:58:54 UTC
Update Date2021-09-14 15:19:56 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

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 Solubility1.81 g/LALOGPS
logP10(0.4) g/LALOGPS
logP10(1.84) g/LChemAxon
logS10(-2) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.92531661259
DarkChem[M-H]-139.66231661259
DeepCCS[M+H]+137.37730932474
DeepCCS[M-H]-134.80130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-oneOC1N=C(O)OCC1C1=CC=CC=C13036.5Standard polar33892256
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-oneOC1N=C(O)OCC1C1=CC=CC=C11693.8Standard non polar33892256
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-oneOC1N=C(O)OCC1C1=CC=CC=C11852.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one,1TMS,isomer #1C[Si](C)(C)OC1N=C(O)OCC1C1=CC=CC=C11871.3Semi standard non polar33892256
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one,1TMS,isomer #2C[Si](C)(C)OC1=NC(O)C(C2=CC=CC=C2)CO11859.5Semi standard non polar33892256
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one,2TMS,isomer #1C[Si](C)(C)OC1=NC(O[Si](C)(C)C)C(C2=CC=CC=C2)CO11864.2Semi standard non polar33892256
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1N=C(O)OCC1C1=CC=CC=C12072.5Semi standard non polar33892256
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC(O)C(C2=CC=CC=C2)CO12077.2Semi standard non polar33892256
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(O[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)CO12280.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-3900000000-5e80893a8f38061556be2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9542000000-a19beedc712ddd9311262017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one 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 - 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one 10V, Positive-QTOFsplash10-000y-0900000000-2871d3961ae9c47cd1b22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one 20V, Positive-QTOFsplash10-001i-0900000000-e4e096245a0bfe98e77d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one 40V, Positive-QTOFsplash10-0ugi-5900000000-fcd193c908acbd29a1372015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one 10V, Negative-QTOFsplash10-0002-0900000000-699a6ff79dbdb21101be2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one 20V, Negative-QTOFsplash10-006x-2900000000-5c875b74d8517b7514a92015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one 40V, Negative-QTOFsplash10-0006-9300000000-360cc92224d8b9fdb3372015-09-15Wishart 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 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
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