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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:09:07 UTC
Update Date2019-07-23 05:58:19 UTC
HMDB IDHMDB0012880
Secondary Accession Numbers
  • HMDB12880
Metabolite Identification
Common NameAcetamidopropanal
DescriptionAcetamidopropanal is associated with urea cycle and metabolism of arginine, proline, glutamate, aspartate and asparagine. Induction of SSAT typically gives rise to growth inhibition or apoptosis, depending upon the cell type and the extent of enzyme overexpression. In such experiments, growth inhibition has been closely linked to depletion of intracellular polyamine pools ( 12) and disturbances in polyamine metabolism ( 13), whereas apoptosis has been associated with downstream events emanating from polyamine oxidase-mediated oxidation of acetylated polyamines and the associated release of oxidatively reactive by-products such as hydrogen peroxide and the aldehyde, 3-acetamidopropanal.
Structure
Data?1563861499
Synonyms
ValueSource
N-(3-Oxopropyl)acetamideHMDB
3-AcetamidopropanalHMDB
3AAPHMDB
Chemical FormulaC5H9NO2
Average Molecular Weight115.1305
Monoisotopic Molecular Weight115.063328537
IUPAC NameN-(3-oxopropyl)acetamide
Traditional Name3-acetamidopropanal
CAS Registry NumberNot Available
SMILES
CC(=O)NCCC=O
InChI Identifier
InChI=1S/C5H9NO2/c1-5(8)6-3-2-4-7/h4H,2-3H2,1H3,(H,6,8)
InChI KeyARJPPNFIEQKVBB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Acetamide
  • Alpha-hydrogen aldehyde
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility40.2 g/LALOGPS
logP-0.72ALOGPS
logP-1.3ChemAxon
logS-0.46ALOGPS
pKa (Strongest Acidic)14.04ChemAxon
pKa (Strongest Basic)-0.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.17 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.22 m³·mol⁻¹ChemAxon
Polarizability11.84 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9000000000-2fd8f331300ecec41733JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-9400000000-96af2337747118e7c7c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-360094019abfd8c935c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-502da3a602b5dc853ebaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-7900000000-f6f97128f599e916de40JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-9200000000-0c22b16b8ae0695c6949JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-91c2f294e835e5ec066bJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030406
KNApSAcK IDNot Available
Chemspider ID4574010
KEGG Compound IDC18170
BioCyc IDCPD-10687
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5460495
PDB IDNot Available
ChEBI ID30322
Food Biomarker OntologyNot Available
VMH IDCE4788
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Flavoenzyme which catalyzes the oxidation of N(1)-acetylspermine to spermidine and is thus involved in the polyamine back-conversion. Can also oxidize N(1)-acetylspermidine to putrescine. Substrate specificity: N(1)-acetylspermine = N(1)-acetylspermidine > N(1),N(12)-diacylspermine >> spermine. Does not oxidize spermidine. Plays an important role in the regulation of polyamine intracellular concentration and has the potential to act as a determinant of cellular sensitivity to the antitumor polyamine analogs.
Gene Name:
PAOX
Uniprot ID:
Q6QHF9
Molecular weight:
55512.64
Reactions
N1-Acetylspermine + Oxygen + Water → Spermidine + Acetamidopropanal + Hydrogen peroxidedetails
N1-Acetylspermidine + Oxygen + Water → Putrescine + Acetamidopropanal + Hydrogen peroxidedetails