benzyl N-[(1S)-1-{[(1S)-5-amino-1-{[(1S)-3-(methylsulfanyl)-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}propyl]carbamoyl}pentyl]carbamoyl}-2-methylpropyl]carbamate

• ChemBase ID: 106338
• Molecular Formular: C34H42F3N5O7S
• Molecular Mass: 721.7867896
• Monoisotopic Mass: 721.27570437
• SMILES: CSCC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CCSC)NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C34H42F3N5O7S/c1-20(2)29(42-33(47)48-19-21-9-5-4-6-10-21)32(46)41-25(11-7-8-15-38)31(45)40-26(14-16-50-3)30(44)39-22-12-13-23-24(34(35,36)37)18-28(43)49-27(23)17-22/h4-6,9-10,12-13,17-18,20,25-26,29H,7-8,11,14-16,19,38H2,1-3H3,(H,39,44)(H,40,45)(H,41,46)(H,42,47)/t25-,26-,29-/m0/s1
• InChIKey: QACWZXGNCWKZPK-ZEZDXWPOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(1S)-5-amino-1-{[(1S)-3-(methylsulfanyl)-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}propyl]carbamoyl}pentyl]carbamoyl}-2-methylpropyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(1S)-5-amino-1-{[(1S)-3-(methylsulfanyl)-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}propyl]carbamoyl}pentyl]carbamoyl}-2-methylpropyl]carbamate
• Synonyms: Z-Val-Lys-Met-AFC; Z-VKM-AFC; Z-Val-Lys-Met-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105410
• PubChem CID: 25108558

CALCULATED PROPERTIES

• Acid pKa: 11.665003
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 0.8021883
• LogD (pH = 7.4): 1.2235388
• Log P: 3.681107
• Molar Refractivity: 183.151 cm^3
• Polarizability: 69.69597 Å^3
• Polar Surface Area: 177.95 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC115

A fluorogenic substrate for Amyloid A4-Generating Enzyme.

REFERENCES

• Ishiura, S. et al., Neurosci. Lett., 115:323 (1990).