3-Aminopropionaldehyde (YMDB00048)

Identification
YMDB IDYMDB00048
Name3-Aminopropionaldehyde
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Aminopropionaldehyde, also known as 3-aminopropanal, 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. 3-Aminopropionaldehyde is a very strong basic compound (based on its pKa). 3-Aminopropionaldehyde exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 3-Aminopropanal
  • 3-Aminopropionaldehyde
  • b-Aminopropion aldehyde
  • beta-Aminopropion aldehyde
  • β-aminopropion aldehyde
CAS number352-92-1
WeightAverage: 73.0938
Monoisotopic: 73.052763851
InChI KeyPCXDJQZLDDHMGX-UHFFFAOYSA-N
InChIInChI=1S/C3H7NO/c4-2-1-3-5/h3H,1-2,4H2
IUPAC Name3-aminopropanal
Traditional IUPAC Name3-aminopropanal
Chemical FormulaC3H7NO
SMILES[H]N([H])C([H])([H])C([H])([H])C([H])=O
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
  • Alpha-hydrogen aldehyde
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility444 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.78 m³·mol⁻¹ChemAxon
Polarizability7.71 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
Spermine + water + oxygen → Hydrogen peroxide + 3-Aminopropionaldehyde + Spermidine
3-Aminopropionaldehyde + water + NADP → Beta-Alanine + hydron + NADPH
KEGG Reactions
NAD + 3-Aminopropionaldehyde + water → NADH + Beta-Alanine + hydron
water + oxygen + N1-Acetylspermidine → 3-Aminopropionaldehyde + Hydrogen peroxide + N-Acetylputrescine
N1-Acetylspermine + water + oxygen → 3-Aminopropionaldehyde + Hydrogen peroxide + N1-Acetylspermidine
Spermine + water + oxygen → Spermidine + 3-Aminopropionaldehyde + Hydrogen peroxide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-13fb77ed3773ab13b10fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-9000000000-8e068317c3b7ab851129JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-e78722b5912332b96551JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-63fc6b8083111d21b561JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-bfbb5311d3b0abfbe795JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-68e71bb6c15dff78a8c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-8780aca699fa02169cf4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-796247bade5fd5732593JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-1ec800454111a0c64d46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a2ff71f6703a0a4daa57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-bc974757d0839ce6b57cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-04ae037d22ea245042cfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-be4ae43b8bb9483fb624JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • White, W. H., Skatrud, P. L., Xue, Z., Toyn, J. H. (2003). "Specialization of function among aldehyde dehydrogenases: the ALD2 and ALD3 genes are required for beta-alanine biosynthesis in Saccharomyces cerevisiae." Genetics 163:69-77.12586697
Synthesis Reference:Bott, 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.
External Links:
ResourceLink
CHEBI ID18090
HMDB IDHMDB01106
Pubchem Compound ID75
Kegg IDC05665
ChemSpider ID74
FOODB IDFDB030407
Wikipedia IDNot Available
BioCyc ID3-AMINO-PROPANAL

Enzymes

Protein Details
1. Aldehyde dehydrogenase [NAD(P)+] 1
General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD2
Uniprot ID:
P47771
Molecular weight:
55187.39844
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.
Protein Details
2. Aldehyde dehydrogenase [NAD(P)+] 2
General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD3
Uniprot ID:
P54114
Molecular weight:
55384.80078
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.
Protein Details
3. Polyamine oxidase FMS1
General function:
Amino acid transport and metabolism
Specific function:
Involved in the production of beta-alanine, a precursor of pantothenic acid. Multicopy suppressor of fenpropimorph resistance
Gene Name:
FMS1
Uniprot ID:
P50264
Molecular weight:
57805.10156
Reactions
Spermine + O(2) + H(2)O → spermidine + 3-aminopropanal + H(2)O(2).
Spermidine + O(2) + H(2)O → putrescine + 3-aminopropanal + H(2)O(2).
N(1)-acetylspermine + O(2) + H(2)O → spermidine + 3-acetamidopropanal + H(2)O(2).
N(1)-acetylspermidine + O(2) + H(2)O → putrescine + 3-acetamidopropanal + H(2)O(2).
N(8)-acetylspermidine + O(2) + H(2)O → 4-acetamidobutanal + trimethylenediamine + H(2)O(2).