benzyl N-[(1S)-1-[({[(1S)-4-carbamimidamido-1-[(4-nitrophenyl)carbamoyl]butyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamate

• ChemBase ID: 106649
• Molecular Formular: C27H36N8O7
• Molecular Mass: 584.62414
• Monoisotopic Mass: 584.27069553
• SMILES: CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])NC(=O)CNC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C27H36N8O7/c1-17(2)23(34-27(39)42-16-18-7-4-3-5-8-18)25(38)31-15-22(36)33-21(9-6-14-30-26(28)29)24(37)32-19-10-12-20(13-11-19)35(40)41/h3-5,7-8,10-13,17,21,23H,6,9,14-16H2,1-2H3,(H,31,38)(H,32,37)(H,33,36)(H,34,39)(H4,28,29,30)/t21-,23-/m0/s1
• InChIKey: PPUGEVRMBYCGHM-GMAHTHKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-[({[(1S)-4-carbamimidamido-1-[(4-nitrophenyl)carbamoyl]butyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-[({[(1S)-4-carbamimidamido-1-[(4-nitrophenyl)carbamoyl]butyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamate
• Synonyms: Z-Val-Gly-Arg-PNA; Z-VGR-PNA; Z-Val-Gly-Arg-paranitroanilide

Database IDs

• PubChem SID: 162105600
• PubChem CID: 21126464

CALCULATED PROPERTIES

• Acid pKa: 12.075957
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -1.1217501
• LogD (pH = 7.4): -1.1162673
• Log P: 0.80818254
• Molar Refractivity: 164.3016 cm^3
• Polarizability: 58.05919 Å^3
• Polar Surface Area: 233.35 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA166

A colorimetric substrate for Urokinase.

REFERENCES

• Marata, M.A. et al., Can. Res., 48:4158 (1988).
• Shori, D.K. et al., Biochem. Pharm., 43(6):1209 (1992).
• Chan, K. et al., Diabetes, 42:113 (1993).