(2S)-2-aminobut-3-ynoic acid

• ChemBase ID: 3830
• Molecular Formular: C4H5NO2
• Molecular Mass: 99.088
• Monoisotopic Mass: 99.03202841
• SMILES: N[C@@H](C#C)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)C#C
• InChI: InChI=1S/C4H5NO2/c1-2-3(5)4(6)7/h1,3H,5H2,(H,6,7)/t3-/m0/s1
• InChIKey: DSUAJFIEKRKPEE-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-aminobut-3-ynoic acid
• IUPAC Traditional name: L-propargylglycine; L-2-amino-3-butynoic acid
• Synonyms: L-C-Propargylglycine; L-2-amino-3-butynoic acid; 2-amino-but-3-ynoic acid; Antibiotic FR 900130; (S)-2-Amino-3-butynoic acid; (S)-2-Amino-4-pentynoic acid; L-C-Propargylglycine; L-Propargylglycine

Database IDs

• CAS Number: 73537-09-4; 23235-01-0
• MDL Number: MFCD00077855
• Beilstein Number: 2347861
• PubChem SID: 24887908; 160967267; 46505992
• PubChem CID: 175496

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.6608694
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.968969
• LogD (pH = 7.4): -3.0170567
• Log P: -2.968635
• Molar Refractivity: 23.3289 cm^3
• Polarizability: 9.10405 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.22
• LOG S: -1.82
• Solubility (Water): 1.50e+00 g/l

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C5H7NO2

DETAILS

DrugBank - DB04217

Drug information: experimental

Sigma Aldrich - 81838

Application
Reagent for the irreversible inactivation of γ-cystathionase1,2; affinity labeling reagent for γ-cystathionase and other enzymes3; peptides containing this amino acid can be tritiated to high specific radioactivity4
Biochem/physiol Actions
L-C-Propargylglycine, a specific inhibitor of H(2)S synthase of cystathionine-γ-lyase (CSE), may be used to study the role of H2S in regulation of biological processes.
L-propargylglycine (PAG), an inhibitor of cystathionine γ-lyase (CSE), is useful in studies of hydrogen sulphide synthesis and bioactivity.