2-aminopent-4-ynoic acid

• ChemBase ID: 155366
• Molecular Formular: C5H7NO2
• Molecular Mass: 113.11458
• Monoisotopic Mass: 113.04767847
• SMILES: C#CCC(C(=O)O)N
• Canonical SMILES: NC(C(=O)O)CC#C
• InChI: InChI=1S/C5H7NO2/c1-2-3-4(6)5(7)8/h1,4H,3,6H2,(H,7,8)
• InChIKey: DGYHPLMPMRKMPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-aminopent-4-ynoic acid
• IUPAC Traditional name: propargylglycine
• Synonyms: 2-Amino-4-pentynoic acid; PAG; DL-Propargylglycine; 2-aminopent-4-ynoic acid

Database IDs

• CAS Number: 64165-64-6
• MDL Number: MFCD00056728
• PubChem SID: 162249504; 24898885
• PubChem CID: 95575

CALCULATED PROPERTIES

• Acid pKa: 2.1471238
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.6809363
• LogD (pH = 7.4): -2.6872406
• Log P: -2.6810064
• Molar Refractivity: 28.0839 cm^3
• Polarizability: 10.924374 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Hydrophobicity(logP): -3.024

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C5H7NO2

DETAILS

Sigma Aldrich - P7888

Biochem/physiol Actions
DL-Propargylglycine (PAG) is an irreversible inhibitor of the enzyme cystathionine γ-lyase (GCL), a key enzyme involved in glutathione synthesis1 and the metabolic transsulfuration pathway which regulates homocysteine concentration and mediates cysteine synthesis.2 Treatment of animal disease models with PAG was shown to alleviate symptoms of diseases that impair the formation or action of hydrogen sulfide (H2S).3,4