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

• ChemBase ID: 106654
• Molecular Formular: C27H36N8O5
• Molecular Mass: 552.62534
• Monoisotopic Mass: 552.28086629
• SMILES: N[C@H](Cc1ccccc1)C(=O)N1CCCC[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]1CCCCN1C(=O)[C@@H](Cc1ccccc1)N
• InChI: InChI=1S/C27H36N8O5/c28-21(17-18-7-2-1-3-8-18)26(38)34-16-5-4-10-23(34)25(37)33-22(9-6-15-31-27(29)30)24(36)32-19-11-13-20(14-12-19)35(39)40/h1-3,7-8,11-14,21-23H,4-6,9-10,15-17,28H2,(H,32,36)(H,33,37)(H4,29,30,31)/t21-,22+,23+/m1/s1
• InChIKey: YDMBNDUHUNWWRP-VJBWXMMDSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105603
• PubChem CID: 123853

CALCULATED PROPERTIES

• Acid pKa: 12.20871
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -3.3741007
• LogD (pH = 7.4): -1.7015399
• Log P: 0.7794263
• Molar Refractivity: 161.02899 cm^3
• Polarizability: 56.87622 Å^3
• Polar Surface Area: 212.25 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false