3-{[(1S)-1-{[(2S)-4-methyl-1-[(2S)-2-{[(1S)-1-[(4-nitrophenyl)carbamoyl]-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}ethyl]carbamoyl}propanoic acid

• ChemBase ID: 106646
• Molecular Formular: C33H42N6O9
• Molecular Mass: 666.72138
• Monoisotopic Mass: 666.30132695
• SMILES: CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: CC(C[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])Cc1ccccc1)NC(=O)[C@@H](NC(=O)CCC(=O)O)C)C
• InChI: InChI=1S/C33H42N6O9/c1-20(2)18-26(37-30(43)21(3)34-28(40)15-16-29(41)42)33(46)38-17-7-10-27(38)32(45)36-25(19-22-8-5-4-6-9-22)31(44)35-23-11-13-24(14-12-23)39(47)48/h4-6,8-9,11-14,20-21,25-27H,7,10,15-19H2,1-3H3,(H,34,40)(H,35,44)(H,36,45)(H,37,43)(H,41,42)/t21-,25-,26-,27-/m0/s1
• InChIKey: RGNLNVHDRHWWDQ-ZYEMSUIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1S)-1-{[(2S)-4-methyl-1-[(2S)-2-{[(1S)-1-[(4-nitrophenyl)carbamoyl]-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}ethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(1S)-1-{[(2S)-4-methyl-1-[(2S)-2-{[(1S)-1-[(4-nitrophenyl)carbamoyl]-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}ethyl]carbamoyl}propanoic acid
• Synonyms: Suc-Ala-Leu-Pro-Phe-PNA; Suc-ALPF-PNA; Suc-Ala-Leu-Pro-Phe-paranitroanilide

Database IDs

• PubChem SID: 162105727
• PubChem CID: 24860364

CALCULATED PROPERTIES

• Acid pKa: 4.0904903
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 0.5900073
• LogD (pH = 7.4): -1.092081
• Log P: 2.0128293
• Molar Refractivity: 174.3103 cm^3
• Polarizability: 66.42659 Å^3
• Polar Surface Area: 219.83 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA163

A colorimetric substrate for Chymotrypsin.

REFERENCES

• Kofron, J.L. et al., Biochem., 30:6127 (1991).