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

• ChemBase ID: 177135
• Molecular Formular: C33H31N3O5
• Molecular Mass: 549.61634
• Monoisotopic Mass: 549.22637111
• SMILES: c1ccc2c3c1ccc1c3c(cc2)c(cc1)CCCC(=O)NCC(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)O
• Canonical SMILES: O=C(NCC(=O)NCC(=O)N[C@H](C(=O)O)Cc1ccccc1)CCCc1ccc2c3c1ccc1c3c(cc2)ccc1
• InChI: InChI=1S/C33H31N3O5/c37-28(34-19-29(38)35-20-30(39)36-27(33(40)41)18-21-6-2-1-3-7-21)11-5-8-22-12-13-25-15-14-23-9-4-10-24-16-17-26(22)32(25)31(23)24/h1-4,6-7,9-10,12-17,27H,5,8,11,18-20H2,(H,34,37)(H,35,38)(H,36,39)(H,40,41)/t27-/m0/s1
• InChIKey: HTURFCDSXIXFGP-MHZLTWQESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 228414-53-7
• PubChem SID: 164233045
• PubChem CID: 45040301

CALCULATED PROPERTIES

• Acid pKa: 3.8412137
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 2.0576491
• LogD (pH = 7.4): 0.47708035
• Log P: 3.720054
• Molar Refractivity: 154.7556 cm^3
• Polarizability: 63.42582 Å^3
• Polar Surface Area: 124.6 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P981060

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)
• Kumar, C.V. et al.: PNAS, 95, 10361-10366 (1998)