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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:56:43 UTC
Update Date2021-09-14 15:47:01 UTC
HMDB IDHMDB0060366
Secondary Accession Numbers
  • HMDB60366
Metabolite Identification
Common Name3-Carbamoyl-2-phenylpropionaldehyde
Description3-Carbamoyl-2-phenylpropionaldehyde belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 3-Carbamoyl-2-phenylpropionaldehyde is a metabolite of felbamate. 3-Carbamoyl-2-phenylpropionaldehyde is a strong basic compound (based on its pKa). 3-Carbamoyl-2-phenylpropionaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, 3-carbamoyl-2-phenylpropionaldehyde participates in a number of enzymatic reactions. In particular, 3-carbamoyl-2-phenylpropionaldehyde can be biosynthesized from 2-phenyl-1,3-propanediol monocarbamate through the action of the enzyme alcohol dehydrogenase 1A. In addition, 3-carbamoyl-2-phenylpropionaldehyde can be converted into 3-carbamoyl-2-phenylpropionic acid; which is catalyzed by the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In humans, 3-carbamoyl-2-phenylpropionaldehyde is involved in felbamate metabolism pathway. Felbamate (marketed under the brand name Felbatol by MedPointe) is an anti-epileptic drug used in the treatment of epilepsy. However, an increased risk of potentially fatal aplastic anemia and/or liver failure limit the drugs usage to severe refractory 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.
Structure
Data?1563866050
Synonyms
ValueSource
3-C-2-PPMeSH
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
Description Belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
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
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 Solubility0.42 g/LALOGPS
logP10(0.79) g/LALOGPS
logP10(1.61) g/LChemAxon
logS10(-2.7) g/LALOGPS
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
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]+143.64231661259
DarkChem[M-H]-139.00731661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Carbamoyl-2-phenylpropionaldehydeOC(=N)OCC(C=O)C1=CC=CC=C13112.6Standard polar33892256
3-Carbamoyl-2-phenylpropionaldehydeOC(=N)OCC(C=O)C1=CC=CC=C11658.6Standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehydeOC(=N)OCC(C=O)C1=CC=CC=C11753.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Carbamoyl-2-phenylpropionaldehyde,1TMS,isomer #1C[Si](C)(C)OC(=N)OCC(C=O)C1=CC=CC=C11841.7Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,1TMS,isomer #2C[Si](C)(C)OC=C(COC(=N)O)C1=CC=CC=C11983.0Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,1TMS,isomer #3C[Si](C)(C)N=C(O)OCC(C=O)C1=CC=CC=C11864.1Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TMS,isomer #1C[Si](C)(C)OC=C(COC(=N)O[Si](C)(C)C)C1=CC=CC=C12001.5Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TMS,isomer #1C[Si](C)(C)OC=C(COC(=N)O[Si](C)(C)C)C1=CC=CC=C11874.3Standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TMS,isomer #1C[Si](C)(C)OC=C(COC(=N)O[Si](C)(C)C)C1=CC=CC=C12534.9Standard polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TMS,isomer #2C[Si](C)(C)N=C(OCC(C=O)C1=CC=CC=C1)O[Si](C)(C)C1808.4Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TMS,isomer #2C[Si](C)(C)N=C(OCC(C=O)C1=CC=CC=C1)O[Si](C)(C)C1806.2Standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TMS,isomer #2C[Si](C)(C)N=C(OCC(C=O)C1=CC=CC=C1)O[Si](C)(C)C2320.2Standard polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TMS,isomer #3C[Si](C)(C)N=C(O)OCC(=CO[Si](C)(C)C)C1=CC=CC=C12021.2Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TMS,isomer #3C[Si](C)(C)N=C(O)OCC(=CO[Si](C)(C)C)C1=CC=CC=C11795.3Standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TMS,isomer #3C[Si](C)(C)N=C(O)OCC(=CO[Si](C)(C)C)C1=CC=CC=C12516.0Standard polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,3TMS,isomer #1C[Si](C)(C)N=C(OCC(=CO[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C1969.1Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,3TMS,isomer #1C[Si](C)(C)N=C(OCC(=CO[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C1860.8Standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,3TMS,isomer #1C[Si](C)(C)N=C(OCC(=CO[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C2321.7Standard polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=N)OCC(C=O)C1=CC=CC=C12082.0Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(COC(=N)O)C1=CC=CC=C12227.4Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C(O)OCC(C=O)C1=CC=CC=C12112.4Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(COC(=N)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12452.5Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(COC(=N)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12288.6Standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(COC(=N)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12712.5Standard polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(OCC(C=O)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2279.8Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(OCC(C=O)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2189.9Standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(OCC(C=O)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2494.7Standard polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C(O)OCC(=CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C12454.2Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C(O)OCC(=CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C12173.6Standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C(O)OCC(=CO[Si](C)(C)C(C)(C)C)C1=CC=CC=C12723.4Standard polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,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)C2611.5Semi standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,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)C2403.2Standard non polar33892256
3-Carbamoyl-2-phenylpropionaldehyde,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)C2625.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-6900000000-fa874ebe5fa0b2992a342017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-5910000000-2ab47f25286068a974302017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 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-phenylpropionaldehyde 10V, Positive-QTOFsplash10-0006-1900000000-861f03fd06b28adf2d722015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 20V, Positive-QTOFsplash10-001l-3900000000-859068b6eca74fe65e602015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 40V, Positive-QTOFsplash10-0kc6-9500000000-a623a0b728a68f8820452015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 10V, Negative-QTOFsplash10-0006-9300000000-d41c87d7b6b803965ef72015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 20V, Negative-QTOFsplash10-0006-9100000000-11125679c7a2d9d813802015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 40V, Negative-QTOFsplash10-0006-9100000000-46659e8588bdd7fe72ec2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 10V, Positive-QTOFsplash10-0a4i-0900000000-d1a5a04766c8392eb6352021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 20V, Positive-QTOFsplash10-0a4i-0900000000-81f45df7ba9401a9ec6a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 40V, Positive-QTOFsplash10-0006-9400000000-730a4ef0832cd02094db2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 10V, Negative-QTOFsplash10-00kf-8900000000-9461db8c23907bb9b1fb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 20V, Negative-QTOFsplash10-0006-9000000000-c44fc3a2c5e7875c71f12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Carbamoyl-2-phenylpropionaldehyde 40V, Negative-QTOFsplash10-00kf-9700000000-d7067c68a367e90501912021-10-12Wishart 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 IDC16587
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21350391
PDB IDNot Available
ChEBI ID80586
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 ]

Only showing the first 10 proteins. There are 11 proteins in total.

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

Only showing the first 10 proteins. There are 11 proteins in total.