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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:13:06 UTC
Update Date2021-09-14 15:25:43 UTC
HMDB IDHMDB0060245
Secondary Accession Numbers
  • HMDB60245
Metabolite Identification
Common NameL-3-Cyanoalanine
DescriptionL-3-Cyanoalanine, also known as L-beta-cyanoalanine, 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. L-3-Cyanoalanine is a very strong basic compound (based on its pKa). L-3-Cyanoalanine exists in all living organisms, ranging from bacteria to humans. Outside of the human body, L-3-cyanoalanine has been detected, but not quantified in, several different foods, such as summer savouries, orange bell peppers, red rices, mixed nuts, and green bell peppers. This could make L-3-cyanoalanine a potential biomarker for the consumption of these foods.
Structure
Data?1583444775
Synonyms
ValueSource
L-beta-CyanoalanineChEBI, KEGG
L-b-CyanoalanineGenerator
L-β-CyanoalanineGenerator
beta-CyanoalanineMeSH, HMDB
3-CyanoalanineMeSH, HMDB
beta-Cyano-L-alanineMeSH, HMDB
3-Cyanoalanine, (L)-isomerMeSH, HMDB
L-3-CyanoalanineKEGG, ChEBI
(2S)-2-Amino-3-cyanopropanoic acidHMDB
(2S)-2-Amino-3-cyanopropionic acidHMDB
2-Amino-3-cyanopropanoic acidHMDB
2-Amino-3-cyanopropionic acidHMDB
3-Cyano-L-alanineHMDB
L-2-Amino-3-cyanopropanoic acidHMDB
L-2-Amino-3-cyanopropionic acidHMDB
β-Cyano-L-alanineHMDB
β-CyanoalanineHMDB
Chemical FormulaC4H6N2O2
Average Molecular Weight114.1026
Monoisotopic Molecular Weight114.042927446
IUPAC Name(2S)-2-amino-3-cyanopropanoic acid
Traditional Name3-cyanoalanine
CAS Registry Number6232-19-5
SMILES
N[C@@H](CC#N)C(O)=O
InChI Identifier
InChI=1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)/t3-/m0/s1
InChI KeyBXRLWGXPSRYJDZ-VKHMYHEASA-N
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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility31.3 g/LALOGPS
logP10(-2.4) g/LALOGPS
logP10(-3.4) g/LChemAxon
logS10(-0.56) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.11731661259
DarkChem[M-H]-118.65531661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-3-Cyanoalanine,1TMS,#1C[Si](C)(C)OC(=O)[C@@H](N)CC#N1282.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-3-Cyanoalanine,1TMS,#2C[Si](C)(C)N[C@@H](CC#N)C(=O)O1356.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-3-Cyanoalanine,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC#N1498.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-3-Cyanoalanine,1TBDMS,#2CC(C)(C)[Si](C)(C)N[C@@H](CC#N)C(=O)O1592.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - L-3-Cyanoalanine GC-MS (2 TMS)splash10-0006-2910000000-cdae81bdd716faf914cb2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-3-Cyanoalanine EI-B (Non-derivatized)splash10-0006-0910000000-76fcf98a116d8f5fb3a32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-3-Cyanoalanine GC-EI-TOF (Non-derivatized)splash10-0006-0900000000-87a768329cbe7349b1292017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Cyanoalanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9000000000-b588e4f0716ef2c3b6ea2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Cyanoalanine GC-MS (1 TMS) - 70eV, Positivesplash10-014i-9100000000-84aa6cdc91672d2d0c402017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Cyanoalanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Cyanoalanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine LC-ESI-QFT , negative-QTOFsplash10-0002-9000000000-fe247d540e001b5b738b2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine LC-ESI-QTOF 35V, negative-QTOFsplash10-0006-9000000000-0b174b164285773536122020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine n/a 7V, negative-QTOFsplash10-0udi-9000000000-b9d26a1c944b0649cadc2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine n/a 7V, negative-QTOFsplash10-0002-9000000000-f17c4c09160c2e81931a2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 2V, negative-QTOFsplash10-0002-9000000000-c35c2982261090e1ac282020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 2V, negative-QTOFsplash10-0002-9000000000-970b9d3c7c142d5bc7ba2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 2V, negative-QTOFsplash10-0002-9000000000-1638709f55d082c648352020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 3V, negative-QTOFsplash10-0002-9000000000-cc48714167e1ba803c7c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 0V, negative-QTOFsplash10-03di-0900000000-45c3feae2e1ceff7377d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 0V, negative-QTOFsplash10-03di-0900000000-bf090b5f90b37f228ec42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 0V, negative-QTOFsplash10-03di-1900000000-48b98dfc454b8b5ef5d42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 0V, negative-QTOFsplash10-03di-2900000000-7490f45dd2e226996a582020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 1V, negative-QTOFsplash10-03di-4900000000-ba685d69c16b14e76f7f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 1V, negative-QTOFsplash10-03dj-9800000000-9eb50c4dbae9090478e72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 2V, negative-QTOFsplash10-01ot-9400000000-d239b0a8038ad871ad6b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 2V, negative-QTOFsplash10-0002-9200000000-1e9123df57023d1425922020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 2V, negative-QTOFsplash10-0002-9100000000-bee64b38054305fe23fc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 3V, negative-QTOFsplash10-0002-9000000000-36456509bbb17410a4c02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Cyanoalanine Orbitrap 3V, negative-QTOFsplash10-0002-9000000000-a9cd3d6dc542f1ebd0b32020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Cyanoalanine 10V, Positive-QTOFsplash10-014j-9200000000-0e19a40d51dba814046f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Cyanoalanine 20V, Positive-QTOFsplash10-0gb9-9000000000-43854410a8c06907e4422015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Cyanoalanine 40V, Positive-QTOFsplash10-0fr6-9000000000-f4e0d1a95b214a75ce612015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Cyanoalanine 10V, Negative-QTOFsplash10-03di-5900000000-b63ea9f293d3ea49c11b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Cyanoalanine 20V, Negative-QTOFsplash10-03dj-9300000000-f9254862ccdb5dd595af2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Cyanoalanine 40V, Negative-QTOFsplash10-0006-9000000000-6b92c9baa9ac2b6575762015-09-15Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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
FooDB IDFDB030412
KNApSAcK IDC00001350
Chemspider ID388802
KEGG Compound IDC02512
BioCyc IDCPD-603
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439742
PDB IDNot Available
ChEBI ID16934
Food Biomarker OntologyNot Available
VMH IDHC00955
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Enzymes

General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:
GGT1
Uniprot ID:
P19440
Molecular weight:
61409.67
Reactions
L-3-Cyanoalanine + L-Glutamic acid → gamma-Glutamyl-beta-cyanoalanine + Waterdetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT7
Uniprot ID:
Q9UJ14
Molecular weight:
70466.015
Reactions
L-3-Cyanoalanine + L-Glutamic acid → gamma-Glutamyl-beta-cyanoalanine + Waterdetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT6
Uniprot ID:
Q6P531
Molecular weight:
50508.83
Reactions
L-3-Cyanoalanine + L-Glutamic acid → gamma-Glutamyl-beta-cyanoalanine + Waterdetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:
GGT5
Uniprot ID:
P36269
Molecular weight:
62331.75
Reactions
L-3-Cyanoalanine + L-Glutamic acid → gamma-Glutamyl-beta-cyanoalanine + Waterdetails