(2S)-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]-2-[(2S)-pyrrolidin-2-ylformamido]pentanamide

• ChemBase ID: 106290
• Molecular Formular: C21H25F3N6O4
• Molecular Mass: 482.4562096
• Monoisotopic Mass: 482.18893797
• SMILES: NC(=N)NCCC[C@H](NC(=O)[C@H]1NCCC1)C(=O)Nc1cc2oc(=O)cc(c2cc1)C(F)(F)F
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H]1CCCN1
• InChI: InChI=1S/C21H25F3N6O4/c22-21(23,24)13-10-17(31)34-16-9-11(5-6-12(13)16)29-19(33)15(4-2-8-28-20(25)26)30-18(32)14-3-1-7-27-14/h5-6,9-10,14-15,27H,1-4,7-8H2,(H,29,33)(H,30,32)(H4,25,26,28)/t14-,15-/m0/s1
• InChIKey: UCTSYYYHIJKWHA-GJZGRUSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]-2-[(2S)-pyrrolidin-2-ylformamido]pentanamide
• IUPAC Traditional name: (2S)-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]-2-[(2S)-pyrrolidin-2-ylformamido]pentanamide
• Synonyms: Pro-Arg-AFC; PR-AFC; Pro-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105383
• PubChem CID: 25108512

CALCULATED PROPERTIES

• Acid pKa: 11.457346
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -5.219822
• LogD (pH = 7.4): -4.0968447
• Log P: -0.099246666
• Molar Refractivity: 127.7699 cm^3
• Polarizability: 43.44132 Å^3
• Polar Surface Area: 158.43 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC032

A fluorogenic substrate for Cathepsin C (DPP-I).