(2R)-3-phenyl-2-{2-[4-(pyren-1-yl)butanamido]acetamido}propanoic acid

• ChemBase ID: 177134
• Molecular Formular: C31H28N2O4
• Molecular Mass: 492.56502
• Monoisotopic Mass: 492.20490739
• SMILES: c1ccc2c3c1ccc1c3c(cc2)c(cc1)CCCC(=O)NCC(=O)N[C@H](Cc1ccccc1)C(=O)O
• Canonical SMILES: O=C(NCC(=O)N[C@@H](C(=O)O)Cc1ccccc1)CCCc1ccc2c3c1ccc1c3c(cc2)ccc1
• InChI: InChI=1S/C31H28N2O4/c34-27(32-19-28(35)33-26(31(36)37)18-20-6-2-1-3-7-20)11-5-8-21-12-13-24-15-14-22-9-4-10-23-16-17-25(21)30(24)29(22)23/h1-4,6-7,9-10,12-17,26H,5,8,11,18-19H2,(H,32,34)(H,33,35)(H,36,37)/t26-/m1/s1
• InChIKey: YRYXBJSINXOFKS-AREMUKBSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-phenyl-2-{2-[4-(pyren-1-yl)butanamido]acetamido}propanoic acid
• IUPAC Traditional name: (2R)-3-phenyl-2-{2-[4-(pyren-1-yl)butanamido]acetamido}propanoic acid
• Synonyms: Py-Gly-Phe; N-[1-Oxo-4-(1-pyrenyl)butyl]glycyl-L-phenylalanine; N-4-(1-Pyrene)butyroylglycyl-L-phenylalanine

Database IDs

• CAS Number: 228414-52-6
• PubChem SID: 164233044
• PubChem CID: 71751883

CALCULATED PROPERTIES

• Acid pKa: 3.8518639
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.173212
• LogD (pH = 7.4): 1.5875407
• Log P: 4.8253374
• Molar Refractivity: 141.9521 cm^3
• Polarizability: 58.588985 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P981050

Of interest for the investigation of site specific photocleavage of proteins.

REFERENCES

• Kumar, C.V. and Buranaprapuk, A.: J. Am. Chem. Soc., 121, 4262-4270 (1999)