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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:56:43 UTC
Update Date2017-10-23 19:15:41 UTC
HMDB IDHMDB0060366
Secondary Accession Numbers
  • HMDB60366
Metabolite Identification
Common Name3-Carbamoyl-2-phenylpropionaldehyde
Description3-Carbamoyl-2-phenylpropionaldehyde is a metabolite of felbamate. Felbamate (marketed under the brand name Felbatol by MedPointe) is an anti-epileptic drug used in the treatment of epilepsy. 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. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC10H11NO3
Average Molecular Weight193.1992
Monoisotopic Molecular Weight193.073893223
IUPAC Name3-(C-hydroxycarbonimidoyloxy)-2-phenylpropanal
Traditional Name3-(C-hydroxycarbonimidoyloxy)-2-phenylpropanal
CAS Registry NumberNot Available
SMILES
OC(=N)OCC(C=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H11NO3/c11-10(13)14-7-9(6-12)8-4-2-1-3-5-8/h1-6,9H,7H2,(H2,11,13)
InChI KeyXUCMSYZLYLONTH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • Carbamic acid ester
  • Carbonic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

  Organ and components:

Source:

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 Solubility0.41 g/LALOGPS
logP0.79ALOGPS
logP1.61ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)8.13ChemAxon
pKa (Strongest Basic)4.67ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity61.82 m³·mol⁻¹ChemAxon
Polarizability19.33 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-6900000000-fa874ebe5fa0b2992a34View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-5910000000-2ab47f25286068a97430View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-861f03fd06b28adf2d72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-3900000000-859068b6eca74fe65e60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kc6-9500000000-a623a0b728a68f882045View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9300000000-d41c87d7b6b803965ef7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-11125679c7a2d9d81380View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-46659e8588bdd7fe72ecView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Felbamate Metabolism PathwayPw000609Pw000609 greyscalePw000609 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
      DrugBank Metabolite IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16587
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound0
      PDB IDNot Available
      ChEBI ID80586
      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 oxidoreductase activity
      Specific function:
      ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
      Gene Name:
      ALDH3A1
      Uniprot ID:
      P30838
      Molecular weight:
      50394.57
      Reactions
      3-Carbamoyl-2-phenylpropionaldehyde + NAD + Water → 3-Carbamoyl-2-phenylpropionic acid + NADH + Hydrogen Iondetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
      Gene Name:
      ALDH1A3
      Uniprot ID:
      P47895
      Molecular weight:
      56107.995
      Reactions
      3-Carbamoyl-2-phenylpropionaldehyde + NAD + Water → 3-Carbamoyl-2-phenylpropionic acid + NADH + Hydrogen Iondetails
      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 oxidoreductase activity
      Specific function:
      Not Available
      Gene Name:
      ALDH3B2
      Uniprot ID:
      P48448
      Molecular weight:
      42623.62
      Reactions
      3-Carbamoyl-2-phenylpropionaldehyde + NAD + Water → 3-Carbamoyl-2-phenylpropionic acid + NADH + Hydrogen Iondetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
      Gene Name:
      ALDH3B1
      Uniprot ID:
      P43353
      Molecular weight:
      51839.245
      Reactions
      3-Carbamoyl-2-phenylpropionaldehyde + NAD + Water → 3-Carbamoyl-2-phenylpropionic acid + 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