(4S)-4-{[(1S)-5-amino-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}pentyl]carbamoyl}-4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-imidazol-4-yl)propanamido]butanoic acid

• ChemBase ID: 106369
• Molecular Formular: C35H38F3N7O9
• Molecular Mass: 757.7129296
• Monoisotopic Mass: 757.26831049
• SMILES: NCCCC[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)OCc1ccccc1)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NCCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H](NC(=O)[C@H](Cc1nc[nH]c1)NC(=O)OCc1ccccc1)CCC(=O)O
• InChI: InChI=1S/C35H38F3N7O9/c36-35(37,38)24-16-30(48)54-28-15-21(9-10-23(24)28)42-31(49)25(8-4-5-13-39)43-32(50)26(11-12-29(46)47)44-33(51)27(14-22-17-40-19-41-22)45-34(52)53-18-20-6-2-1-3-7-20/h1-3,6-7,9-10,15-17,19,25-27H,4-5,8,11-14,18,39H2,(H,40,41)(H,42,49)(H,43,50)(H,44,51)(H,45,52)(H,46,47)/t25-,26-,27-/m0/s1
• InChIKey: XYLYPIJCFOIGQR-QKDODKLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-5-amino-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}pentyl]carbamoyl}-4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-imidazol-4-yl)propanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-5-amino-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}pentyl]carbamoyl}-4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-imidazol-4-yl)propanamido]butanoic acid
• Synonyms: Z-His-Glu-Lys-AFC; Z-HEK-AFC; Z-His-Glu-Lys-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105620
• PubChem CID: 25108588

CALCULATED PROPERTIES

• Acid pKa: 3.5046947
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -1.5463225
• LogD (pH = 7.4): -0.8109751
• Log P: -0.7759973
• Molar Refractivity: 184.8531 cm^3
• Polarizability: 70.06468 Å^3
• Polar Surface Area: 243.93 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC248

A Cysteine protease substrate for Lys-Gingipain.

REFERENCES

• Abe, N. et al., J. Biochem., 128(5):877 (2000).