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3-Cyano-L-alanine (M2MDB000915)

Record Information
Version2.0
Creation Date2012-05-31 14:25:41 -0600
Update Date2015-06-03 17:19:14 -0600
Secondary Accession Numbers
  • ECMDB20066
Identification
Name:3-Cyano-L-alanine
Description3-cyano-L-alanine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 3-Cyano-L-alanine
  • 3-Cyanoalanine
  • b-cyano-L-Alanine
  • Beta-Cyano-L-alanine
  • C9650_SIGMA
  • L-3-Cyanoalanine
  • L-b-Cyanoalanine
  • L-beta-Cyanoalanine
  • L-β-Cyanoalanine
  • β-cyano-L-Alanine
Chemical Formula:C4H6N2O2
Weight:Average: 114.1026
Monoisotopic: 114.042927446
InChI Key:BXRLWGXPSRYJDZ-VKHMYHEASA-N
InChI:InChI=1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)/t3-/m0/s1
CAS number:6232-19-5
IUPAC Name:(2S)-2-amino-3-cyanopropanoic acid
Traditional IUPAC Name:3-cyanoalanine
SMILES:[H][C@](N)(CC#N)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility31.3 g/LALOGPS
logP-2.4ALOGPS
logP-3.4ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)0.23ChemAxon
pKa (Strongest Basic)7.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.11 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.51 m³·mol⁻¹ChemAxon
Polarizability10.27 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
3-Cyano-L-alanine + L-Glutamate <> gamma-Glutamyl-beta-cyanoalanine + Water
L-Glutamate + 3-Cyano-L-alanine > Water + gamma-Glutamyl-beta-cyanoalanine
SMPDB Pathways:
L-glutamate metabolism IIPW001886 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 - GC-MS (2 TMS)splash10-0006-2910000000-cdae81bdd716faf914cbView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0910000000-76fcf98a116d8f5fb3a3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0900000000-87a768329cbe7349b129View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9000000000-b588e4f0716ef2c3b6eaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-9100000000-84aa6cdc91672d2d0c40View 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-QFT , negativesplash10-0002-9000000000-fe247d540e001b5b738bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0006-9000000000-0b174b16428577353612View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0udi-9000000000-b9d26a1c944b0649cadcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0002-9000000000-f17c4c09160c2e81931aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9000000000-c35c2982261090e1ac28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9000000000-970b9d3c7c142d5bc7baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9000000000-1638709f55d082c64835View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-cc48714167e1ba803c7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-03di-0900000000-45c3feae2e1ceff7377dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-03di-0900000000-bf090b5f90b37f228ec4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-03di-1900000000-48b98dfc454b8b5ef5d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-03di-2900000000-7490f45dd2e226996a58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-03di-4900000000-ba685d69c16b14e76f7fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-03dj-9800000000-9eb50c4dbae9090478e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-01ot-9400000000-d239b0a8038ad871ad6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9200000000-1e9123df57023d142592View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9100000000-bee64b38054305fe23fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-36456509bbb17410a4c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-a9cd3d6dc542f1ebd0b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-006t-9000000000-0923f4b6979f216eb757View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0002-9000000000-dc0d16ea8ae536cb82ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0udi-9000000000-e742d1778ed2916e7989View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9000000000-46983704961d3c708c40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, positivesplash10-00di-9000000000-783db8104c08d8983467View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, positivesplash10-0a4j-8900000000-c3a0f4587b5f55cd8cf9View in MoNA
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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16934
HMDB IDHMDB0060245
Pubchem Compound ID439742
Kegg IDC02512
ChemSpider ID388802
Wikipedia IDNot Available
BioCyc IDCPD0-1336
EcoCyc IDCPD0-1336

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.