(2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(4-nitrophenyl)pentanamide

• ChemBase ID: 106625
• Molecular Formular: C26H34N8O5
• Molecular Mass: 538.59876
• Monoisotopic Mass: 538.26521623
• SMILES: N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=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)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)N
• InChI: InChI=1S/C26H34N8O5/c27-20(16-17-6-2-1-3-7-17)25(37)33-15-5-9-22(33)24(36)32-21(8-4-14-30-26(28)29)23(35)31-18-10-12-19(13-11-18)34(38)39/h1-3,6-7,10-13,20-22H,4-5,8-9,14-16,27H2,(H,31,35)(H,32,36)(H4,28,29,30)/t20-,21+,22+/m1/s1
• InChIKey: POCPPIVLPOPNLF-FSSWDIPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(4-nitrophenyl)pentanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(4-nitrophenyl)pentanamide
• Synonyms: D-Phe-Pro-Arg-PNA; D-FPR-PNA; D-Phe-Pro-Arg-paranitroanilide

Database IDs

• PubChem SID: 162105995
• PubChem CID: 13020982

CALCULATED PROPERTIES

• Acid pKa: 12.190271
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -3.8186681
• LogD (pH = 7.4): -2.1460166
• Log P: 0.32951015
• Molar Refractivity: 156.428 cm^3
• Polarizability: 55.042778 Å^3
• Polar Surface Area: 212.25 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA064

A colorimetric substrate for Thrombin.

REFERENCES

• McRae, B.J. et al., Biochem., 20:7196 (1981).