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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:30:25 UTC
HMDB IDHMDB01106
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Aminopropionaldehyde
Description3-Aminopropanal is a reactive aldehyde that mediates progressive neuronal necrosis and glial apoptosis. (PMID 11943872 ). Increased activity of polyamine oxidase catabolizes polyamines (such as spermine, spermidine and putrescine) to produce 3-aminopropanal. (PMID 15246852 ).
Structure
Thumb
Synonyms
  1. 3-Aminopropanal
  2. 3-Aminopropionaldehyde
  3. beta-Aminopropion aldehyde
Chemical FormulaC3H7NO
Average Molecular Weight73.0938
Monoisotopic Molecular Weight73.052763851
IUPAC Name3-aminopropanal
Traditional Name3-aminopropanal
CAS Registry Number352-92-1
SMILES
NCCC=O
InChI Identifier
InChI=1S/C3H7NO/c4-2-1-3-5/h3H,1-2,4H2
InChI KeyPCXDJQZLDDHMGX-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlkylamines
Sub ClassN/A
Other Descriptors
  • Aldehydes
  • propanals(ChEBI)
Substituents
  • N/A
Direct ParentAlkylamines
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility444.0ALOGPS
logP-1.2ALOGPS
logP-1.1ChemAxon
logS0.78ALOGPS
pKa (Strongest Acidic)14.19ChemAxon
pKa (Strongest Basic)9.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.78 m3·mol-1ChemAxon
Polarizability7.71 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Beta-Alanine MetabolismSMP00007map00410
Normal Concentrations
Not Available
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 IDFDB022427
KNApSAcK IDNot Available
Chemspider ID74
KEGG Compound IDC05665
BioCyc ID3-AMINO-PROPANAL
BiGG ID46232
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01106
Metagene LinkHMDB01106
METLIN ID6007
PubChem Compound75
PDB IDNot Available
ChEBI ID18090
References
Synthesis ReferenceBott, Kaspar. Amidomethylation of trichloroethylene and acetylene: syntheses of N-protected a-chloro-b-alanines and b-aminopropanals. Journal of the Chemical Society [Section] D: Chemical Communications (1969), (22), 1304.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ivanova S, Batliwalla F, Mocco J, Kiss S, Huang J, Mack W, Coon A, Eaton JW, Al-Abed Y, Gregersen PK, Shohami E, Connolly ES Jr, Tracey KJ: Neuroprotection in cerebral ischemia by neutralization of 3-aminopropanal. Proc Natl Acad Sci U S A. 2002 Apr 16;99(8):5579-84. Epub 2002 Apr 9. Pubmed: 11943872
  2. Yu Z, Li W, Hillman J, Brunk UT: Human neuroblastoma (SH-SY5Y) cells are highly sensitive to the lysosomotropic aldehyde 3-aminopropanal. Brain Res. 2004 Aug 6;1016(2):163-9. Pubmed: 15246852

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
3-Aminopropionaldehyde + NAD + Water → Beta-Alanine + NADH + Hydrogen Iondetails
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-Aminopropionaldehyde + NAD + Water → Beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
3-Aminopropionaldehyde + NAD + Water → Beta-Alanine + 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-Aminopropionaldehyde + NAD + Water → Beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
3-Aminopropionaldehyde + NAD + Water → Beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
3-Aminopropionaldehyde + NAD + Water → Beta-Alanine + NADH + Hydrogen Iondetails
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.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
3-Aminopropionaldehyde + NAD + Water → Beta-Alanine + NADH + Hydrogen Iondetails
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
1,3-Diaminopropane + Oxygen + Water → 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Reactions
1,3-Diaminopropane + Oxygen + Water → 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
3-Aminopropionaldehyde + NAD + Water → Beta-Alanine + 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-Aminopropionaldehyde + NAD + Water → Beta-Alanine + NADH + Hydrogen Iondetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Flavoenzyme which catalyzes the oxidation of spermine to spermidine. Can also use N(1)-acetylspermine and spermidine as substrates, with different affinity depending on the isoform (isozyme) and on the experimental conditions. 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. May contribute to beta-alanine production via aldehyde dehydrogenase conversion of 3-amino-propanal.
Gene Name:
SMOX
Uniprot ID:
Q9NWM0
Molecular weight:
65006.29
Reactions
Spermine + Oxygen + Water → Spermidine + 3-Aminopropionaldehyde + Hydrogen peroxidedetails