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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:55:43 UTC
Update Date2021-09-14 15:44:54 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

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 Solubility0.51 g/LALOGPS
logP10(0.27) g/LALOGPS
logP10(1.36) g/LChemAxon
logS10(-2.6) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.83331661259
DarkChem[M-H]-141.00231661259
DeepCCS[M+H]+146.23530932474
DeepCCS[M-H]-143.18730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Phenyl-1,3-propanediol monocarbamateOCC(COC(O)=N)C1=CC=CC=C13140.2Standard polar33892256
2-Phenyl-1,3-propanediol monocarbamateOCC(COC(O)=N)C1=CC=CC=C11837.0Standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamateOCC(COC(O)=N)C1=CC=CC=C11844.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Phenyl-1,3-propanediol monocarbamate,1TMS,isomer #1C[Si](C)(C)OCC(COC(=N)O)C1=CC=CC=C11880.6Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,1TMS,isomer #2C[Si](C)(C)OC(=N)OCC(CO)C1=CC=CC=C11869.9Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,1TMS,isomer #3C[Si](C)(C)N=C(O)OCC(CO)C1=CC=CC=C11892.3Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,2TMS,isomer #1C[Si](C)(C)OCC(COC(=N)O[Si](C)(C)C)C1=CC=CC=C11870.7Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,2TMS,isomer #2C[Si](C)(C)N=C(O)OCC(CO[Si](C)(C)C)C1=CC=CC=C11908.3Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,2TMS,isomer #3C[Si](C)(C)N=C(OCC(CO)C1=CC=CC=C1)O[Si](C)(C)C1798.4Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,3TMS,isomer #1C[Si](C)(C)N=C(OCC(CO[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C1810.8Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,3TMS,isomer #1C[Si](C)(C)N=C(OCC(CO[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C1872.3Standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,3TMS,isomer #1C[Si](C)(C)N=C(OCC(CO[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C2198.2Standard polar33892256
2-Phenyl-1,3-propanediol monocarbamate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(COC(=N)O)C1=CC=CC=C12110.5Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=N)OCC(CO)C1=CC=CC=C12094.8Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C(O)OCC(CO)C1=CC=CC=C12136.4Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(COC(=N)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12337.1Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(O)OCC(CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C12348.9Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C(OCC(CO)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2285.2Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(OCC(CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2494.3Semi standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(OCC(CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2410.0Standard non polar33892256
2-Phenyl-1,3-propanediol monocarbamate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(OCC(CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2526.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenyl-1,3-propanediol monocarbamate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-5900000000-995f4eb6e2633b22bcd62017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenyl-1,3-propanediol monocarbamate GC-MS (2 TMS) - 70eV, Positivesplash10-00r6-7930000000-8860ae14d9b0eb3596052017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenyl-1,3-propanediol monocarbamate 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 - 2-Phenyl-1,3-propanediol monocarbamate 10V, Positive-QTOFsplash10-004j-1900000000-81c107fe4ce7a216b46b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenyl-1,3-propanediol monocarbamate 20V, Positive-QTOFsplash10-002r-2900000000-7eb6ccb9e5825420460a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenyl-1,3-propanediol monocarbamate 40V, Positive-QTOFsplash10-0fbl-8900000000-a30281ef0e6c4b25cf102015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenyl-1,3-propanediol monocarbamate 10V, Negative-QTOFsplash10-0006-9300000000-47a0ff21e4406bfd4b5c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenyl-1,3-propanediol monocarbamate 20V, Negative-QTOFsplash10-0006-9100000000-9e1f6a966217a8e230be2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenyl-1,3-propanediol monocarbamate 40V, Negative-QTOFsplash10-0006-9200000000-e6f43d7792d3bc0d17af2015-09-15Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 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
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
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