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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:55:43 UTC
Update Date2019-07-23 07:14:08 UTC
HMDB IDHMDB0060351
Secondary Accession Numbers
  • HMDB60351
Metabolite Identification
Common Name2-Phenyl-1,3-propanediol monocarbamate
Description2-Phenyl-1,3-propanediol monocarbamate 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. 2-Phenyl-1,3-propanediol monocarbamate is a strong basic compound (based on its pKa). 2-Phenyl-1,3-propanediol monocarbamate exists in all living organisms, ranging from bacteria to humans. 2-phenyl-1,3-propanediol monocarbamate can be converted into 3-carbamoyl-2-phenylpropionaldehyde through the action of the enzyme alcohol dehydrogenase 1A. In humans, 2-phenyl-1,3-propanediol monocarbamate 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. However, an increased risk of potentially fatal aplastic anemia and/or liver failure limit the drugs usage to severe refractory epilepsy. Felbamate (marketed under the brand name Felbatol by MedPointe) is an anti-epileptic drug used in the treatment of epilepsy. 2-Phenyl-1,3-propanediol monocarbamate is a metabolite of felbamate.
Structure
Data?1563866048
Synonyms
ValueSource
2-Phenyl-1,3-propanediol monocarbamic acidGenerator
Chemical FormulaC10H13NO3
Average Molecular Weight195.2151
Monoisotopic Molecular Weight195.089543287
IUPAC Name3-(C-hydroxycarbonimidoyloxy)-2-phenylpropan-1-ol
Traditional Name3-(C-hydroxycarbonimidoyloxy)-2-phenylpropan-1-ol
CAS Registry NumberNot Available
SMILES
OCC(COC(O)=N)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H13NO3/c11-10(13)14-7-9(6-12)8-4-2-1-3-5-8/h1-5,9,12H,6-7H2,(H2,11,13)
InChI KeyJQVQIZWJBLGVRW-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
  • Monocyclic benzene moiety
  • Carbamic acid ester
  • Carbonic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.51 g/LALOGPS
logP0.27ALOGPS
logP1.36ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.36ChemAxon
pKa (Strongest Basic)4.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.54 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.96 m³·mol⁻¹ChemAxon
Polarizability20.24 ųChemAxon
Number of Rings1ChemAxon
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-5900000000-995f4eb6e2633b22bcd6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00r6-7930000000-8860ae14d9b0eb359605Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1900000000-81c107fe4ce7a216b46bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-2900000000-7eb6ccb9e5825420460aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbl-8900000000-a30281ef0e6c4b25cf10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9300000000-47a0ff21e4406bfd4b5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-9e1f6a966217a8e230beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-e6f43d7792d3bc0d17afSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 IDC16586
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound213060
      PDB IDNot Available
      ChEBI ID80585
      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
      2-Phenyl-1,3-propanediol monocarbamate + NAD → 3-Carbamoyl-2-phenylpropionaldehyde + 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
      2-Phenyl-1,3-propanediol monocarbamate + NAD → 3-Carbamoyl-2-phenylpropionaldehyde + 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
      2-Phenyl-1,3-propanediol monocarbamate + NAD → 3-Carbamoyl-2-phenylpropionaldehyde + 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
      2-Phenyl-1,3-propanediol monocarbamate + NAD → 3-Carbamoyl-2-phenylpropionaldehyde + 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
      2-Phenyl-1,3-propanediol monocarbamate + NAD → 3-Carbamoyl-2-phenylpropionaldehyde + 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
      2-Phenyl-1,3-propanediol monocarbamate + NAD → 3-Carbamoyl-2-phenylpropionaldehyde + 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
      2-Phenyl-1,3-propanediol monocarbamate + NAD → 3-Carbamoyl-2-phenylpropionaldehyde + NADH + Hydrogen Iondetails