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

• ChemBase ID: 106580
• Molecular Formular: C50H57N9O8
• Molecular Mass: 912.04308
• Monoisotopic Mass: 911.43300983
• SMILES: COc1cc(NC(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc2ccccc2)NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC(=O)OCc2ccccc2)cc2c1cccc2
• Canonical SMILES: COc1cc(NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)CNC(=O)[C@@H](NC(=O)OCc2ccccc2)CCCNC(=N)N)Cc2ccccc2)cc2c1cccc2
• InChI: InChI=1S/C50H57N9O8/c1-66-43-30-37(29-36-21-11-12-22-38(36)43)55-47(63)42-24-14-26-59(42)48(64)41(28-34-17-7-3-8-18-34)57-46(62)40(27-33-15-5-2-6-16-33)56-44(60)31-54-45(61)39(23-13-25-53-49(51)52)58-50(65)67-32-35-19-9-4-10-20-35/h2-12,15-22,29-30,39-42H,13-14,23-28,31-32H2,1H3,(H,54,61)(H,55,63)(H,56,60)(H,57,62)(H,58,65)(H4,51,52,53)/t39-,40-,41-,42-/m0/s1
• InChIKey: SKJNXCDWXUDXGG-IWWWZYECSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-4-carbamimidamido-1-[({[(1S)-1-{[(2S)-1-[(2S)-2-[(4-methoxynaphthalen-2-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-methoxynaphthalen-2-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-MNA; Z-RGFFP-MNA; Z-Arg-Gly-Phe-Phe-Pro-4-Methoxy-2-Naphthylamine

Database IDs

• PubChem SID: 162105592
• PubChem CID: 25108733

CALCULATED PROPERTIES

• Acid pKa: 11.598618
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): 1.3948506
• LogD (pH = 7.4): 1.3998919
• Log P: 3.3155606
• Molar Refractivity: 262.4166 cm^3
• Polarizability: 98.015335 Å^3
• Polar Surface Area: 246.17 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MNA098

A fluorogenic/colorimetric substrate for Cathespin D. Suitable for either colorimetric or fluorometric assay. Cathepsin D hydrolyzes the Phe-Phe bond. Requires dipeptidyl aminopeptidase II to free 4-methoxy-b-naphthylamine (MNA).

REFERENCES

• Lojda, Z., et al., Biochem., Biophys. Res. Comm., 148:335 (1987)
• Gulmik,S. et al., Mol. Bio., 277:265