(2S)-1-acetylpyrrolidine-2-carboxylic acid

• ChemBase ID: 18291
• Molecular Formular: C7H11NO3
• Molecular Mass: 157.16714
• Monoisotopic Mass: 157.07389322
• SMILES: N1([C@H](C(=O)O)CCC1)C(=O)C
• Canonical SMILES: CC(=O)N1CCC[C@H]1C(=O)O
• InChI: InChI=1S/C7H11NO3/c1-5(9)8-4-2-3-6(8)7(10)11/h6H,2-4H2,1H3,(H,10,11)/t6-/m0/s1
• InChIKey: GNMSLDIYJOSUSW-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-acetylpyrrolidine-2-carboxylic acid
• IUPAC Traditional name: acetylproline
• Synonyms: Ac-Pro-OH; (S)-1-Acetyl-pyrrolidine-2-carboxylic acid; N-ACETYL-L-PROLINE; N-Acetyl-L-proline; N-乙酰-L-脯氨酸

Database IDs

• CAS Number: 68-95-1
• EC Number: 200-698-9
• MDL Number: MFCD00020837
• Beilstein Number: 83200
• PubChem SID: 160981598; 24890453
• PubChem CID: 66141

CALCULATED PROPERTIES

• Acid pKa: 3.8935208
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.099141
• LogD (pH = 7.4): -3.7041261
• Log P: -0.48719913
• Molar Refractivity: 37.6302 cm^3
• Polarizability: 14.72032 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 117-118°C
• Optical Rotation: -116 (c=1 in water)

Safety Information

• Storage Condition: 0°C
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 99%
• Empirical Formula (Hill Notation): C7H11NO3

DETAILS

Sigma Aldrich - A0783

Biochem/physiol Actions
N-Acetyl-L-proline, an analog of the COOH-terminal dipeptide portion of preferred angiotensin-converting enzyme substrates, is use to probe the active site of angiotensin-converting enzyme(s). N-Acetyl-L-proline may be used to to identify, differentiate and characterized N-acyl-amino acid amidohydrolase(s)/aminoacylase(s). N-Acetyl-L-proline is used to study the physicochemical parameters of prolines.
N-acetyl-L-proline is an analog of the COOH-terminal dipeptide portion of preferred substrates of angiotensin-converting enzyme (ACE). It may be used in studies of the binding of substrates and inhibitors by ACE and to differentiate the specificities of various aminoacylases.