(2S)-2-[(2S)-2-[(2S)-2-[(2-aminophenyl)formamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(4-nitrophenyl)propanoic acid

• ChemBase ID: 106259
• Molecular Formular: C31H36N8O7
• Molecular Mass: 632.66694
• Monoisotopic Mass: 632.27069553
• SMILES: NC(=N)NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccccc1N)C(=O)N[C@@H](Cc1ccc(cc1)[N+](=O)[O-])C(=O)O
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)N[C@H](C(=O)O)Cc1ccc(cc1)[N+](=O)[O-])NC(=O)[C@@H](NC(=O)c1ccccc1N)Cc1ccccc1
• InChI: InChI=1S/C31H36N8O7/c32-23-10-5-4-9-22(23)27(40)37-25(17-19-7-2-1-3-8-19)29(42)36-24(11-6-16-35-31(33)34)28(41)38-26(30(43)44)18-20-12-14-21(15-13-20)39(45)46/h1-5,7-10,12-15,24-26H,6,11,16-18,32H2,(H,36,42)(H,37,40)(H,38,41)(H,43,44)(H4,33,34,35)/t24-,25-,26-/m0/s1
• InChIKey: XGNOCNFNYWGDBR-GSDHBNRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2-aminophenyl)formamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(4-nitrophenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2-aminophenyl)formamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(4-nitrophenyl)propanoic acid
• Synonyms: Abz-Phe-Arg-Phe(NO2)-OH; Abz-FRF(NO2)-OH; Abz-Phe-Arg-Phe(NO2)-OH

Database IDs

• PubChem SID: 162105372
• PubChem CID: 25108482

CALCULATED PROPERTIES

• Acid pKa: 3.2056105
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): 0.5378659
• LogD (pH = 7.4): 0.53977144
• Log P: 0.5397464
• Molar Refractivity: 179.8953 cm^3
• Polarizability: 63.486115 Å^3
• Polar Surface Area: 258.34 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03ABZ001

A fluorogenic substrate for Cathepsin X.

REFERENCES

• Dorit, K. et al., Biochem., 38:12648 (1999).