(2S)-2-azaniumyl-3-cyanopropanoate
Basic information
- CAS
6232-19-5- Standard SMILES
N#CC[C@H]([NH3+])C(=O)[O-]- InChIKey
BXRLWGXPSRYJDZ-VKHMYHEASA-N- Molecular formula
- C4H6N2O2
- Average molar mass
- 114.1 g/mol
- Monoisotopic mass
- 114.04292744
Overview
3-cyano-L-alanine zwitterion is an L-alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of 3-cyano-L-alanine. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.). It is a conjugate acid of a 3-cyano-L-alaninate. It is a tautomer of a 3-cyano-L-alanine.
Names & identifiers
- Preferred name
- (2S)-2-azaniumyl-3-cyanopropanoate
- IUPAC
- (2S)-2-azaniumyl-3-cyanopropanoate
- English name
- beta-Cyano-L-alanine
- Molecular formula
- C4H6N2O2
- Molecular weight
- 114.1
Names & synonyms
(2S)-2-azaniumyl-3-cyanopropanoate3-cyano-L-alanine zwitterionCHEBI:77860(2S)-2-ammonio-3-cyanopropanoate3-CYANO-L-ALANINEH-CPA-OH(S)-2-Amino-3-cyanopropanoic acidL-CNAlaH-ALA(3-CN)-OHH-b-Cyano-Ala-OHH-β-Cyano-Ala-OHβ-Cyano-L-Ala-OH
Show more names
H-ALA(BETA-CN)-OHB-cyano-L-alanine
Database identifiers
- CAS
6232-19-5- PubChem CID
- 6971253
- ChEBI
CHEBI:77860
Properties
Computed structural properties
- XLogP
- -3
- Topological polar surface area
- 91.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 129
Physicochemical properties
- Melting point
- 217 °C · 217 °C
- storage temp.
- -20 °C · -20°C
- solubility
- PBS (pH 7.2): 10 mg/ml
- form
- A crystalline solid
- color
- White to yellow
- InChI
- 1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)/t3-/m0/s1
- InChIKey
- BXRLWGXPSRYJDZ-VKHMYHEASA-N
- SMILES
- OC([C@@H](N)CC#N)=O
- FDA UNII
- 75 AJA4DCJ · B75AJA4DCJ
- UNSPSC Code
- 12352209 · 12352209
- NACRES
- 26 · NA.26
- WGK Germany
- 3 · 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionHydrogen sulfide (H2S) is a naturally-occurring gasotransmitter with vasodilator and inflammatory modulating activity. H2S is synthesized naturally in a range of mammalian tissues principally by the activity of two enzymes, cystathionine γ lyase (CSE) and cystathionine β synthetase (CBS). β-cyano-L-Alanine (BCA) is a reversible inhibitor of the H2S-synthesizing enzyme CSE. BCA blocks H2S synthesis in rat liver preparations with an IC50 value of 6.5 μM and increases blood pressure in anaesthetized rats induced with hemorrhagic shock by inhibiting endogenous H2S synthesis. BCA at 50 mg/kg blocked both L-cysteine- and LPS-induced hyperalgesia in rats.
Usesβ-L-cyanoalanine is an amino acid that promotes seed germination in A. albus seeds. Beta-Cyano-L-alanine in the diet of adult locusts causes a decrease in the hemolymph volume thereby affecting water balance responses. L-β-cyanoalanine is an inhibitor of vitamin B6.
Additional notes
DefinitionChEBI: A cyanoamino acid that is the 3-cyano-derivative of L-alanine.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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