N-(1-{2-[(1-carbamoyl-2-hydroxyethyl)carbamoyl]pyrrolidin-1-yl}-3-hydroxy-1-oxobutan-2-yl)pyrrolidine-2-carboxamide

• ChemBase ID: 131666
• Molecular Formular: C17H29N5O6
• Molecular Mass: 399.44206
• Monoisotopic Mass: 399.21178367
• SMILES: CC(C(C(=O)N1CCCC1C(=O)NC(CO)C(=O)N)NC(=O)C1CCCN1)O
• Canonical SMILES: OCC(C(=O)N)NC(=O)C1CCCN1C(=O)C(C(O)C)NC(=O)C1CCCN1
• InChI: InChI=1S/C17H29N5O6/c1-9(24)13(21-15(26)10-4-2-6-19-10)17(28)22-7-3-5-12(22)16(27)20-11(8-23)14(18)25/h9-13,19,23-24H,2-8H2,1H3,(H2,18,25)(H,20,27)(H,21,26)
• InChIKey: UMIXOKDUTWTCDE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(1-{2-[(1-carbamoyl-2-hydroxyethyl)carbamoyl]pyrrolidin-1-yl}-3-hydroxy-1-oxobutan-2-yl)pyrrolidine-2-carboxamide
• IUPAC Traditional name: N-(1-{2-[(1-carbamoyl-2-hydroxyethyl)carbamoyl]pyrrolidin-1-yl}-3-hydroxy-1-oxobutan-2-yl)pyrrolidine-2-carboxamide
• Synonyms: Pro-Thr-Pro-Ser amide

Database IDs

• CAS Number: 121269-85-0
• MDL Number: MFCD00133782
• PubChem SID: 162225943
• PubChem CID: 4283477

CALCULATED PROPERTIES

• Acid pKa: 11.659428
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -7.091199
• LogD (pH = 7.4): -5.9964676
• Log P: -3.9182203
• Molar Refractivity: 96.974 cm^3
• Polarizability: 38.389004 Å^3
• Polar Surface Area: 174.09 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - P8179

Biochem/physiol Actions
Inhibits proteolysis of IgA by Neisseria gonorrheae protease type I
Other Notes
Analog of the hinge region of human IgA2