Showing Compound Card for L-3-Cyanoalanine (CDB005063)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:05:38 UTC
Updated at2020-11-18 16:39:16 UTC
CannabisDB IDCDB005063
Secondary Accession NumbersNot Available
Cannabis Compound 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 savories, 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. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). L-3-Cyanoalanine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight114.1
Monoisotopic Molecular Weight114.0429
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
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-3-Cyanoalanine, 2 TMS, GC-MS Spectrumsplash10-0006-2910000000-cdae81bdd716faf914cbSpectrum
GC-MSL-3-Cyanoalanine, non-derivatized, GC-MS Spectrumsplash10-0006-0910000000-76fcf98a116d8f5fb3a3Spectrum
GC-MSL-3-Cyanoalanine, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-87a768329cbe7349b129Spectrum
Predicted GC-MSL-3-Cyanoalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-9000000000-b588e4f0716ef2c3b6eaSpectrum
Predicted GC-MSL-3-Cyanoalanine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-9100000000-84aa6cdc91672d2d0c40Spectrum
Predicted GC-MSL-3-Cyanoalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-3-Cyanoalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0002-9000000000-fe247d540e001b5b738b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0006-9000000000-0b174b164285773536122020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0udi-9000000000-b9d26a1c944b0649cadc2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0002-9000000000-f17c4c09160c2e81931a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9000000000-c35c2982261090e1ac282020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9000000000-970b9d3c7c142d5bc7ba2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9000000000-1638709f55d082c648352020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-cc48714167e1ba803c7c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-03di-0900000000-45c3feae2e1ceff7377d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-03di-0900000000-bf090b5f90b37f228ec42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-03di-1900000000-48b98dfc454b8b5ef5d42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-03di-2900000000-7490f45dd2e226996a582020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-03di-4900000000-ba685d69c16b14e76f7f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-03dj-9800000000-9eb50c4dbae9090478e72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-01ot-9400000000-d239b0a8038ad871ad6b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9200000000-1e9123df57023d1425922020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9100000000-bee64b38054305fe23fc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-36456509bbb17410a4c02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-a9cd3d6dc542f1ebd0b32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-006t-9000000000-0923f4b6979f216eb7572020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0002-9000000000-dc0d16ea8ae536cb82eb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0udi-9000000000-e742d1778ed2916e79892020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9000000000-46983704961d3c708c402021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, positivesplash10-00di-9000000000-783db8104c08d89834672020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, positivesplash10-0a4j-8900000000-c3a0f4587b5f55cd8cf92020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Gamma-glutamyltranspeptidase 1GGT122q11.23P19440 details
Gamma-glutamyltransferase 7GGT720q11.22Q9UJ14 details
Gamma-glutamyltransferase 6GGT617p13.2Q6P531 details
Gamma-glutamyltransferase 5GGT522q11.23P36269 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0060245
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Gamma-glutamyltranspeptidase 1
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
Enzyme Details
2. Gamma-glutamyltransferase 7
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT7
Uniprot ID:
Q9UJ14
Molecular weight:
70466.015
Enzyme Details
3. Gamma-glutamyltransferase 6
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT6
Uniprot ID:
Q6P531
Molecular weight:
50508.83
Enzyme Details
4. Gamma-glutamyltransferase 5
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