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Record Information
Version3.6
Creation Date2013-05-17 00:56:47 UTC
Update Date2017-08-18 12:38:58 UTC
HMDB IDHMDB0060367
Secondary Accession Numbers
  • HMDB60367
Metabolite Identification
Common Name3-Carbamoyl-2-phenylpropionic acid
Description3-Carbamoyl-2-phenylpropionic acid 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
Synonyms
ValueSource
3-Carbamoyloxy-2-phenylpropionic acidMeSH
CPPA-3,2MeSH
Chemical FormulaC10H11NO4
Average Molecular Weight209.1986
Monoisotopic Molecular Weight209.068807845
IUPAC Name3-(C-hydroxycarbonimidoyloxy)-2-phenylpropanoic acid
Traditional Name3-(C-hydroxycarbonimidoyloxy)-2-phenylpropanoic acid
CAS Registry NumberNot Available
SMILES
OC(=N)OCC(C(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H11NO4/c11-10(14)15-6-8(9(12)13)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,11,14)(H,12,13)
InChI KeyAYRIVCKWIAUVOO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Carbamic acid ester
  • Carbonic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
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 Solubility0.46 mg/mLALOGPS
logP0.35ALOGPS
logP0.81ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.81ChemAxon
pKa (Strongest Basic)4.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.61 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.75 m3·mol-1ChemAxon
Polarizability20.31 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
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 IDC16591
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0060367
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI 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 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 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