Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


beta-Aminopropionitrile (M2MDB001424)

Record Information
Version2.0
Creation Date2012-05-31 14:54:07 -0600
Update Date2015-09-13 12:56:14 -0600
Secondary Accession Numbers
  • ECMDB21004
Identification
Name:beta-Aminopropionitrile
DescriptionBeta-Aminopropionitrile is a toxic amino-acid derivative. It is an metabolite in beta-alanine metabolism and converted to beta-alanine. It is also an intermediate in cyanoamino acid metablism. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • β-alaminenitrile
  • β-alaninenitrile
  • β-cyanoethylamine
  • 2-Cyanoethylamine
  • 3-amino-propatenitrile
  • 3-amino-propionitrile,
  • 3-Aminopropanenitrile
  • 3-Aminopropionitrile
  • 3-Aminopropiononitrile
  • Aminopropionitrile
  • B-Alaminenitrile
  • B-Alaninenitrile
  • B-Aminoethyl cyanide
  • B-Aminopropionitrile
  • B-Cyanoethylamine
  • BAPN
  • Beta-Alaminenitrile
  • Beta-Alaninenitrile
  • Beta-Aminoethyl cyanide
  • Beta-Aminopropionitrile
  • Beta-Cyanoethylamine
  • β-Alaminenitrile
  • β-Alaninenitrile
  • β-Aminoethyl cyanide
  • β-Aminopropionitrile
  • β-Cyanoethylamine
Chemical Formula:C3H6N2
Weight:Average: 70.0931
Monoisotopic: 70.053098202
InChI Key:AGSPXMVUFBBBMO-UHFFFAOYSA-N
InChI:InChI=1S/C3H6N2/c4-2-1-3-5/h1-2,4H2
CAS number:151-18-8
IUPAC Name:3-aminopropanenitrile
Traditional IUPAC Name:β aminopropionitrile
SMILES:NCCC#N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitriles. Nitriles are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOrganic cyanides
Direct ParentNitriles
Alternative Parents
Substituents
  • Nitrile
  • Carbonitrile
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:1
Melting point:< 25 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility37 g/LALOGPS
logP-1.1ALOGPS
logP-0.85ChemAxon
logS-0.28ALOGPS
pKa (Strongest Basic)7.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.81 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity19.68 m³·mol⁻¹ChemAxon
Polarizability7.53 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
beta-Aminopropionitrile + L-Glutamate <> gamma-Glutamyl-beta-aminopropiononitrile + Water
SMPDB Pathways:
beta-Alanine metabolismPW000896 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-f05f2291dfe77fc789cbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-3900000000-75972f9c9d6ba1c09de2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9800000000-a9d53e8af368cf281f3cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-9640000000-2a51789533a4a0d4beedView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-2690000000-e7505ee33092ac028fb9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-7900000000-1aa082aac45073e0b837View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-f05f2291dfe77fc789cbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-3900000000-75972f9c9d6ba1c09de2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9800000000-a9d53e8af368cf281f3cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-9640000000-2a51789533a4a0d4beedView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-2690000000-e7505ee33092ac028fb9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-7900000000-1aa082aac45073e0b837View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-3fe507f31005b95d4d19View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-6a162c90ff7c10fa232cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-9000000000-d2707111f575b74b6f7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-f8447d5497483c729855View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-9000000000-bc2e9976335d260923ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-044e599cd4faa32caadbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-9000000000-7dfadb8fdf3477540781View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9000000000-ca5db6c876b46ee9a1cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-39a4d5ba1e275b87d47bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-d13e9e176f608de3e76bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-3b795596647194f89ae6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-9000000000-062a72ed70b3ea0ab27cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-9000000000-2fff615cd0ee0cefe387View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-9000000000-68c0881f62968c46bae3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-adccf0ec306a306afddeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-a14492dbdacb5919bd26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-5a010be4a6fec74e8afdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr6-9000000000-0fbbefce04b1773be5c6View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-e5c8c009efa6f2441041View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Dembinski J, Heyl W, Steidel K, Hermanns B, Hornchen H, Schroder W: The Cantrell-sequence: a result of maternal exposure to aminopropionitriles? Am J Perinatol. 1997 Oct;14(9):567-71. Pubmed: 9394169
  • Fleisher JH, Peacock EE Jr, Chvapil M: Urinary excretion of beta-aminopropionitrile and cyanoacetic acid. Clin Pharmacol Ther. 1978 May;23(5):520-4. Pubmed: 639425
  • Harrison CA, Gossiel F, Bullock AJ, Sun T, Blumsohn A, Mac Neil S: Investigation of keratinocyte regulation of collagen I synthesis by dermal fibroblasts in a simple in vitro model. Br J Dermatol. 2006 Mar;154(3):401-10. Pubmed: 16445767
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Peacock EE Jr: Pharmacological control of surgical scar tissue. Am Surg. 1978 Nov;44(11):693-8. Pubmed: 367235
  • Spencer PS, Schaumburg HH: Lathyrism: a neurotoxic disease. Neurobehav Toxicol Teratol. 1983 Nov-Dec;5(6):625-9. Pubmed: 6422318
Synthesis Reference:Smolin, Edwin M.; Beegle, L. Clair. Continuous high-pressure synthesis of 3-aminopropionitrile. Journal of Industrial and Engineering Chemistry (Washington, D. C.) (1958), 50 1115-18.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID27413
HMDB IDHMDB04101
Pubchem Compound ID1647
Kegg IDC05670
ChemSpider ID21241485
Wikipedia IDAminopropionitrile
BioCyc IDBETA-AMINOPROPIONITRILE
EcoCyc IDBETA-AMINOPROPIONITRILE

Enzymes

Protein Details
1. Gamma-glutamyltranspeptidase
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
(5-L-glutamyl)-peptide + an amino acid = peptide + 5-L-glutamyl amino acid
Gene Name:
ggt
Uniprot ID:
P18956
Molecular weight:
61768
Reactions
A (5-L-glutamyl)-peptide + an amino acid = a peptide + a 5-L-glutamyl amino acid.
Glutathione + H(2)O = L-cysteinylglycine + L-glutamate.