ethyl (2S)-3-phenyl-2-[4-(pyren-1-yl)butanamido]propanoate

• ChemBase ID: 177136
• Molecular Formular: C31H29NO3
• Molecular Mass: 463.56686
• Monoisotopic Mass: 463.21474379
• SMILES: c1ccc2c3c1ccc1c3c(cc2)c(cc1)CCCC(=O)N[C@@H](Cc1ccccc1)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@H](Cc1ccccc1)NC(=O)CCCc1ccc2c3c1ccc1c3c(cc2)ccc1
• InChI: InChI=1S/C31H29NO3/c1-2-35-31(34)27(20-21-8-4-3-5-9-21)32-28(33)13-7-10-22-14-15-25-17-16-23-11-6-12-24-18-19-26(22)30(25)29(23)24/h3-6,8-9,11-12,14-19,27H,2,7,10,13,20H2,1H3,(H,32,33)/t27-/m0/s1
• InChIKey: OTXWSIGCMVMENA-MHZLTWQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-3-phenyl-2-[4-(pyren-1-yl)butanamido]propanoate
• IUPAC Traditional name: ethyl (2S)-3-phenyl-2-[4-(pyren-1-yl)butanamido]propanoate
• Synonyms: Py-Phe, Ethyl Ester; N-[1-Oxo-4-(1-pyrenyl)butyl]-L-phenylalanine Ethyl Ester; N-4-(1-Pyrene)butyroyl-L-phenylalanine Ethyl Ester

Database IDs

• CAS Number: 1331912-17-4
• PubChem SID: 164233046
• PubChem CID: 29986723

CALCULATED PROPERTIES

• Acid pKa: 12.7967
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.4333224
• LogD (pH = 7.4): 6.433321
• Log P: 6.4333224
• Molar Refractivity: 138.6663 cm^3
• Polarizability: 57.749584 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - P981120

Of interest for the investigation of site specific photocleavage of proteins. A n electron acceptor, such as cobalt (III) hexammine (CoHA) is required for this reaction.

REFERENCES

• Kumar, C.V., et al.: PNAS, 95(18). 10361-10366 (1998)
• Kumar, C.V. and Buranaprapuk, A.: J. Am. Chem. Soc., 121, 4262-4270 (1999)