CHEBI:43797 - L-propargylglycine

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ChEBI Name L-propargylglycine
ChEBI ID CHEBI:43797
ChEBI ASCII Name L-propargylglycine
Definition A non-proteinogenic L-α-amino acid that is L-alanine in which one of the methyl hydrogens has been replaced by an ethynyl group. It causes the irreversible inactivation of γ-cystathionase (also known as cystathionine γ-lyase) and is used as an affinity labeling reagent for γ-cystathionase and other enzymes.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C5H7NO2
Net Charge 0
Average Mass 113.116
Monoisotopic Mass 113.04768
InChI InChI=1S/C5H7NO2/c1-2-3-4(6)5(7)8/h1,4H,3,6H2,(H,7,8)/t4-/m0/s1
InChIKey DGYHPLMPMRKMPD-BYPYZUCNSA-N
SMILES C(=O)([C@@H](N)CC#C)O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 2.6.1.2 (alanine transaminase) inhibitor
An EC 2.6.1.* (transaminases) inhibitor that inhibits the action of any alanine transaminase (EC 2.6.1.2).
EC 2.5.1.48 (cystathionine gamma-synthase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of cystathionine gamma-synthase (EC 2.5.1.48).
EC 1.4.3.2 (L-amino-acid oxidase) inhibitor
Any EC 1.4.3.* (oxidoreductase acting on donor CH-NH2 group, oxygen as acceptor) inhibitor that interferes with the action of L-amino-acid oxidase (EC 1.4.3.2).
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ChEBI Ontology
Outgoing L-propargylglycine (CHEBI:43797) has role EC 1.4.3.2 (L-amino-acid oxidase) inhibitor (CHEBI:144097)
L-propargylglycine (CHEBI:43797) has role EC 2.5.1.48 (cystathionine γ-synthase) inhibitor (CHEBI:137566)
L-propargylglycine (CHEBI:43797) has role EC 2.6.1.2 (alanine transaminase) inhibitor (CHEBI:144099)
L-propargylglycine (CHEBI:43797) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
L-propargylglycine (CHEBI:43797) is a terminal acetylenic compound (CHEBI:73477)
L-propargylglycine (CHEBI:43797) is tautomer of L-propargylglycine zwitterion (CHEBI:143285)
Incoming L-β-ethynylserine (CHEBI:144833) has functional parent L-propargylglycine (CHEBI:43797)
L-propargylglycine zwitterion (CHEBI:143285) is tautomer of L-propargylglycine (CHEBI:43797)
IUPAC Name
(2S)-2-aminopent-4-ynoic acid
Synonyms Sources
(S)-2-amino-4-pentynoic acid ChemIDplus
(S)-2-propargylglycine ChemIDplus
(S)-α-propargylglycine ChemIDplus
(S)-propargylglycine ChemIDplus
L-2-propynylglycine ChemIDplus
L-C-propargylglycine ChEBI
L-PROPARGYLGLYCINE PDBeChem
Manual Xref Database
LPG PDBeChem
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Registry Number Type Source
23235-01-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
23772385 PubMed citation Europe PMC
30867596 PubMed citation Europe PMC
387077 PubMed citation Europe PMC
3994731 PubMed citation Europe PMC
7094918 PubMed citation Europe PMC
7364752 PubMed citation Europe PMC
944577 PubMed citation Europe PMC
Last Modified
16 September 2019