tert-butyl N-[(1S)-1-({2-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)ethyl]carbamate

• ChemBase ID: 106344
• Molecular Formular: C31H41F3N8O8
• Molecular Mass: 710.7012496
• Monoisotopic Mass: 710.29994497
• SMILES: C[C@H](NC(=O)OC(C)(C)C)C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@@H](NC(=O)OC(C)(C)C)C
• InChI: InChI=1S/C31H41F3N8O8/c1-16(39-29(48)50-30(2,3)4)25(45)38-15-23(43)42-12-6-8-21(42)27(47)41-20(7-5-11-37-28(35)36)26(46)40-17-9-10-18-19(31(32,33)34)14-24(44)49-22(18)13-17/h9-10,13-14,16,20-21H,5-8,11-12,15H2,1-4H3,(H,38,45)(H,39,48)(H,40,46)(H,41,47)(H4,35,36,37)/t16-,20-,21-/m0/s1
• InChIKey: CWJWEUWOFWNKFY-NDXORKPFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(1S)-1-({2-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)ethyl]carbamate
• IUPAC Traditional name: tert-butyl N-[(1S)-1-({2-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)ethyl]carbamate
• Synonyms: Boc-Ala-Gly-Pro-Arg-AFC; Boc-AGPR-AFC; Boc-Ala-Gly-Pro-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105403
• PubChem CID: 25108564

CALCULATED PROPERTIES

• Acid pKa: 11.454062
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -2.4096444
• LogD (pH = 7.4): -2.4028864
• Log P: -0.53297234
• Molar Refractivity: 182.8659 cm^3
• Polarizability: 64.80861 Å^3
• Polar Surface Area: 234.14 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC121

A fluorogenic substrate for Cathepsin K.

REFERENCES

• Imada, T. et al., Biochem. Biophys. Res. Comm., 143:587 (1987).