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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:56:47 UTC
Update Date2021-09-14 15:47:01 UTC
HMDB IDHMDB0060367
Secondary Accession Numbers
  • HMDB60367
Metabolite Identification
Common Name3-Carbamoyl-2-phenylpropionic acid
Description3-Carbamoyl-2-phenylpropionic acid, also known as cppa-3,2, 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. 3-Carbamoyl-2-phenylpropionic acid is a strong basic compound (based on its pKa). 3-Carbamoyl-2-phenylpropionic acid exists in all living organisms, ranging from bacteria to humans. 3-carbamoyl-2-phenylpropionic acid can be biosynthesized from 3-carbamoyl-2-phenylpropionaldehyde through its interaction with the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In humans, 3-carbamoyl-2-phenylpropionic acid 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. 3-Carbamoyl-2-phenylpropionic acid 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?1563866050
Synonyms
ValueSource
3-Carbamoyl-2-phenylpropionateGenerator
3-Carbamoyloxy-2-phenylpropionic acidHMDB
CPPA-3,2HMDB
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
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
  • 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
Disposition

Biological location

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 Solubility0.46 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.75 m³·mol⁻¹ChemAxon
Polarizability20.31 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]+148.60331661259
DarkChem[M-H]-142.15831661259
DeepCCS[M+H]+145.24830932474
DeepCCS[M-H]-142.85230932474
DeepCCS[M-2H]-176.8630932474
DeepCCS[M+Na]+151.43630932474
AllCCS[M+H]+145.032859911
AllCCS[M+H-H2O]+141.032859911
AllCCS[M+NH4]+148.732859911
AllCCS[M+Na]+149.832859911
AllCCS[M-H]-144.232859911
AllCCS[M+Na-2H]-144.632859911
AllCCS[M+HCOO]-145.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Carbamoyl-2-phenylpropionic acidOC(=N)OCC(C(O)=O)C1=CC=CC=C13501.5Standard polar33892256
3-Carbamoyl-2-phenylpropionic acidOC(=N)OCC(C(O)=O)C1=CC=CC=C11886.1Standard non polar33892256
3-Carbamoyl-2-phenylpropionic acidOC(=N)OCC(C(O)=O)C1=CC=CC=C11956.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Carbamoyl-2-phenylpropionic acid,1TMS,isomer #1C[Si](C)(C)OC(=N)OCC(C(=O)O)C1=CC=CC=C11948.4Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(COC(=N)O)C1=CC=CC=C11922.0Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,1TMS,isomer #3C[Si](C)(C)N=C(O)OCC(C(=O)O)C1=CC=CC=C11931.1Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,2TMS,isomer #1C[Si](C)(C)OC(=N)OCC(C(=O)O[Si](C)(C)C)C1=CC=CC=C11928.8Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,2TMS,isomer #2C[Si](C)(C)N=C(OCC(C(=O)O)C1=CC=CC=C1)O[Si](C)(C)C1872.2Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,2TMS,isomer #3C[Si](C)(C)N=C(O)OCC(C(=O)O[Si](C)(C)C)C1=CC=CC=C11937.2Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,3TMS,isomer #1C[Si](C)(C)N=C(OCC(C(=O)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C1887.4Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,3TMS,isomer #1C[Si](C)(C)N=C(OCC(C(=O)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C1878.9Standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,3TMS,isomer #1C[Si](C)(C)N=C(OCC(C(=O)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C2318.1Standard polar33892256
3-Carbamoyl-2-phenylpropionic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=N)OCC(C(=O)O)C1=CC=CC=C12203.2Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(COC(=N)O)C1=CC=CC=C12149.5Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C(O)OCC(C(=O)O)C1=CC=CC=C12185.4Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=N)OCC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12374.6Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(OCC(C(=O)O)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2366.8Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C(O)OCC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12371.7Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(OCC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2534.7Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(OCC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2451.1Standard non polar33892256
3-Carbamoyl-2-phenylpropionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(OCC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2646.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7900000000-21d0cabcf402c9fcc8852017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid GC-MS (2 TMS) - 70eV, Positivesplash10-05g0-9370000000-1e4048ff289bd86a17902017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 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 - 3-Carbamoyl-2-phenylpropionic acid 10V, Positive-QTOFsplash10-03dl-1950000000-2429ecc36f5e673faff62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 20V, Positive-QTOFsplash10-0gvp-2900000000-f529830b39f6b2c6658a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 40V, Positive-QTOFsplash10-0udl-4900000000-04f47cc7b100beec223a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 10V, Negative-QTOFsplash10-0006-9210000000-1347d51503da39e8e2c72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 20V, Negative-QTOFsplash10-0006-9000000000-2e99ea03877cdcb942f42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 40V, Negative-QTOFsplash10-0006-9200000000-84539f83871e571267f22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-f65f41ca302d0729f2382021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 20V, Positive-QTOFsplash10-0zfr-0900000000-d775a2d92e3064970c342021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 40V, Positive-QTOFsplash10-0ftf-9700000000-8f744bce7d15d6c537042021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 10V, Negative-QTOFsplash10-0udi-1910000000-586673089fef386847942021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 20V, Negative-QTOFsplash10-0006-9100000000-01418b51c562804df3e82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionic acid 40V, Negative-QTOFsplash10-0006-9300000000-3f868bd280f0e85a05152021-10-12Wishart 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 IDC16591
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3025746
PDB IDNot Available
ChEBI ID80589
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 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