(2S)-1-(2-{[(2S)-1-acetylpyrrolidin-2-yl]formamido}acetyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid hydrate

• ChemBase ID: 155024
• Molecular Formular: C16H24F3N3O8
• Molecular Mass: 443.3722696
• Monoisotopic Mass: 443.1515494
• SMILES: CC(=O)N1CCC[C@H]1C(=O)NCC(=O)N1CCC[C@H]1C(=O)O.C(=O)(C(F)(F)F)O.O
• Canonical SMILES: OC(=O)C(F)(F)F.O=C(N1CCC[C@H]1C(=O)O)CNC(=O)[C@@H]1CCCN1C(=O)C.O
• InChI: InChI=1S/C14H21N3O5.C2HF3O2.H2O/c1-9(18)16-6-2-4-10(16)13(20)15-8-12(19)17-7-3-5-11(17)14(21)22;3-2(4,5)1(6)7;/h10-11H,2-8H2,1H3,(H,15,20)(H,21,22);(H,6,7);1H2/t10-,11-;;/m0../s1
• InChIKey: UCOFOXNKITYGTK-ULEGLUPFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-(2-{[(2S)-1-acetylpyrrolidin-2-yl]formamido}acetyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid hydrate
• IUPAC Traditional name: (2S)-1-(2-{[(2S)-1-acetylpyrrolidin-2-yl]formamido}acetyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid hydrate
• Synonyms: 1-Acetyl-L-prolylglycyl-L-proline; Acetyl Pro-Gly-Pro; Acetyl-proline-glycine-proline; N-α-PGP; acPGP; Ac-PGP trifluoroacetate salt hydrate

Database IDs

• CAS Number: 292171-04-1(freebase)
• MDL Number: MFCD20134196
• PubChem SID: 162249162
• PubChem CID: 71312058

CALCULATED PROPERTIES

• Acid pKa: 3.5801616
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -3.7708352
• LogD (pH = 7.4): -5.2062016
• Log P: -1.8563358
• Molar Refractivity: 75.4202 cm^3
• Polarizability: 29.383287 Å^3
• Polar Surface Area: 107.02 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: deionized water: ≥2 mg/mL
• Apperance: white to tan powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C14H21N3O5 · xC2HF3O2 · yH2O

DETAILS

Sigma Aldrich - A2112

Biochem/physiol Actions
N-acetyl Proline-Glycine-Proline (ac-PGP) is a potent and selective neutrophil chemoattractant. It is generated enzymatically from extracellular matrix proteins such as collagen. PGP is generated from native collagen by the action of matrix metalloproteinase-8 (MMP-8) and/or MMP-9, followed by a secondary cleavage by prolyl endopeptidase (PE). N-terminal acetylation of PGP (Ac-PGP) occurs through an unknown mechanism. Both PGP and AcPGP are considered biomarkers and possible therapeutic targets for chronic obstructive pulmonary disease (COPD) and may also be markers for acute pulmonary exacerbation in Cystic Fibrosis.