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

• ChemBase ID: 106460
• Molecular Formular: C35H41N7O9
• Molecular Mass: 703.74154
• Monoisotopic Mass: 703.29657593
• SMILES: Cc1cc(=O)oc2c1ccc(NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)OCc1ccccc1)c2
• Canonical SMILES: NCCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)OCc1ccccc1)CCC(=O)O
• InChI: InChI=1S/C35H41N7O9/c1-21-15-31(45)51-29-17-23(10-11-25(21)29)39-32(46)26(9-5-6-14-36)40-33(47)27(12-13-30(43)44)41-34(48)28(16-24-18-37-20-38-24)42-35(49)50-19-22-7-3-2-4-8-22/h2-4,7-8,10-11,15,17-18,20,26-28H,5-6,9,12-14,16,19,36H2,1H3,(H,37,38)(H,39,46)(H,40,47)(H,41,48)(H,42,49)(H,43,44)/t26-,27-,28-/m0/s1
• InChIKey: DQCGTBDNZFCIMT-KCHLEUMXSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105578
• PubChem CID: 25108647

CALCULATED PROPERTIES

• Acid pKa: 3.5114868
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -1.910806
• LogD (pH = 7.4): -1.1753848
• Log P: -1.1403551
• Molar Refractivity: 183.9206 cm^3
• Polarizability: 70.68488 Å^3
• Polar Surface Area: 243.93 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC248

A Cysteine protease substrate for Lys-Gingipain

REFERENCES

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