benzyl N-{2-[(2S)-2-{[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamate

• ChemBase ID: 106560
• Molecular Formular: C32H39N7O6
• Molecular Mass: 617.69536
• Monoisotopic Mass: 617.296182
• SMILES: COc1cc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]2CCCN2C(=O)CNC(=O)OCc2ccccc2)cc2c1cccc2
• Canonical SMILES: COc1cc(NC(=O)[C@@H](NC(=O)[C@@H]2CCCN2C(=O)CNC(=O)OCc2ccccc2)CCCNC(=N)N)cc2c1cccc2
• InChI: InChI=1S/C32H39N7O6/c1-44-27-18-23(17-22-11-5-6-12-24(22)27)37-29(41)25(13-7-15-35-31(33)34)38-30(42)26-14-8-16-39(26)28(40)19-36-32(43)45-20-21-9-3-2-4-10-21/h2-6,9-12,17-18,25-26H,7-8,13-16,19-20H2,1H3,(H,36,43)(H,37,41)(H,38,42)(H4,33,34,35)/t25-,26-/m0/s1
• InChIKey: GRFKZYIOWWFSLU-UIOOFZCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-{2-[(2S)-2-{[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamate
• IUPAC Traditional name: benzyl N-{2-[(2S)-2-{[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamate
• Synonyms: Z-Gly-Pro-Arg-MNA; Z-GPR-MNA; Z-Gly-Pro-Arg-4-Methoxy-2-Naphthylamine

Database IDs

• PubChem SID: 162105523
• PubChem CID: 25108715

CALCULATED PROPERTIES

• Acid pKa: 12.331405
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -0.8447758
• LogD (pH = 7.4): -0.8406432
• Log P: 1.1969038
• Molar Refractivity: 178.5838 cm^3
• Polarizability: 65.369934 Å^3
• Polar Surface Area: 187.97 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MNA061

A fluorogenic/colorimetric substrate for Granzyme A.

REFERENCES

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