benzyl N-[(1S)-4-carbamimidamido-1-[({[(1S)-1-{[(2S)-1-[(2S)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamoyl}-2-phenylethyl]carbamoyl}methyl)carbamoyl]butyl]carbamate

• ChemBase ID: 106431
• Molecular Formular: C49H55N9O9
• Molecular Mass: 914.0159
• Monoisotopic Mass: 913.41227439
• SMILES: Cc1cc(=O)oc2c1ccc(NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC(=O)OCc1ccccc1)c2
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc2c(c1)oc(=O)cc2C)Cc1ccccc1)Cc1ccccc1)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C49H55N9O9/c1-31-25-43(60)67-41-28-35(21-22-36(31)41)54-46(63)40-20-12-24-58(40)47(64)39(27-33-15-7-3-8-16-33)56-45(62)38(26-32-13-5-2-6-14-32)55-42(59)29-53-44(61)37(19-11-23-52-48(50)51)57-49(65)66-30-34-17-9-4-10-18-34/h2-10,13-18,21-22,25,28,37-40H,11-12,19-20,23-24,26-27,29-30H2,1H3,(H,53,61)(H,54,63)(H,55,59)(H,56,62)(H,57,65)(H4,50,51,52)/t37-,38-,39-,40-/m0/s1
• InChIKey: CZHNVMSBMHCFOQ-YKKXUYLKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-4-carbamimidamido-1-[({[(1S)-1-{[(2S)-1-[(2S)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamoyl}-2-phenylethyl]carbamoyl}methyl)carbamoyl]butyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-4-carbamimidamido-1-[({[(1S)-1-{[(2S)-1-[(2S)-2-[(4-methyl-2-oxochromen-7-yl)carbamoyl]pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamoyl}-2-phenylethyl]carbamoyl}methyl)carbamoyl]butyl]carbamate
• Synonyms: Z-Arg-Gly-Phe-Phe-Pro-AMC; Z-RGFFP-AMC; Z-Arg-Gly-Phe-Phe-Pro-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105987
• PubChem CID: 25108621

CALCULATED PROPERTIES

• Acid pKa: 12.069041
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): 0.672556
• LogD (pH = 7.4): 0.677786
• Log P: 2.5928895
• Molar Refractivity: 259.2758 cm^3
• Polarizability: 95.253395 Å^3
• Polar Surface Area: 263.24 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC098

A fluorogenic substrate for Cathepsin D.

REFERENCES

• Lojda, Z. et al., Histochem., 88:505 (1988).
• Nishimura, Y. et al., Biochem. Biophys. Res. Comm., 148:335.
• Gulmik, S. et al., J. Mol. Bio., 277:265 (1992).