(4S)-4-{[(benzyloxy)carbonyl]amino}-5-[(2S)-2-{[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butyl]carbamoyl}pyrrolidin-1-yl]-5-oxopentanoic acid

• ChemBase ID: 106416
• Molecular Formular: C34H41N7O9
• Molecular Mass: 691.73084
• Monoisotopic Mass: 691.29657593
• SMILES: Cc1cc(=O)oc2c1ccc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)NC(=O)OCc1ccccc1)c2
• Canonical SMILES: O=C(N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)CCCNC(=N)N)CCC(=O)O)OCc1ccccc1
• InChI: InChI=1S/C34H41N7O9/c1-20-17-29(44)50-27-18-22(11-12-23(20)27)38-30(45)24(9-5-15-37-33(35)36)39-31(46)26-10-6-16-41(26)32(47)25(13-14-28(42)43)40-34(48)49-19-21-7-3-2-4-8-21/h2-4,7-8,11-12,17-18,24-26H,5-6,9-10,13-16,19H2,1H3,(H,38,45)(H,39,46)(H,40,48)(H,42,43)(H4,35,36,37)/t24-,25-,26-/m0/s1
• InChIKey: XTQBJRYAQJJLGT-GSDHBNRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(benzyloxy)carbonyl]amino}-5-[(2S)-2-{[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butyl]carbamoyl}pyrrolidin-1-yl]-5-oxopentanoic acid
• IUPAC Traditional name: (4S)-4-{[(benzyloxy)carbonyl]amino}-5-[(2S)-2-{[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]butyl]carbamoyl}pyrrolidin-1-yl]-5-oxopentanoic acid
• Synonyms: Z-Glu-Pro-Arg-AMC; Z-EPR-AMC; Z-Glu-Pro-Arg-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105698
• PubChem CID: 25108606

CALCULATED PROPERTIES

• Acid pKa: 3.674855
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -0.5863273
• LogD (pH = 7.4): -0.5810693
• Log P: -0.58108324
• Molar Refractivity: 190.7273 cm^3
• Polarizability: 68.738754 Å^3
• Polar Surface Area: 242.34 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC061

A fluorogenic substrate for Granzyme A.

REFERENCES

• Smith, M.J. et al., J. Biol. Chem., 267(34):24418.
• Velotti, F. et al., Eur. J. Imm., 22:1049 (1992).