(2S)-3-[(4,5-dimethoxy-2-nitrophenyl)methoxy]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid

• ChemBase ID: 169331
• Molecular Formular: C27H26N2O9
• Molecular Mass: 522.50334
• Monoisotopic Mass: 522.16383042
• SMILES: c1c(c(cc(c1[N+](=O)[O-])COC[C@H](NC(=O)OCC1c2c(c3c1cccc3)cccc2)C(=O)O)OC)OC
• Canonical SMILES: COc1cc(COC[C@@H](C(=O)O)NC(=O)OCC2c3ccccc3c3c2cccc3)c(cc1OC)[N+](=O)[O-]
• InChI: InChI=1S/C27H26N2O9/c1-35-24-11-16(23(29(33)34)12-25(24)36-2)13-37-15-22(26(30)31)28-27(32)38-14-21-19-9-5-3-7-17(19)18-8-4-6-10-20(18)21/h3-12,21-22H,13-15H2,1-2H3,(H,28,32)(H,30,31)/t22-/m0/s1
• InChIKey: GEIDGZJCBUYWDB-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-[(4,5-dimethoxy-2-nitrophenyl)methoxy]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid
• IUPAC Traditional name: (2S)-3-[(4,5-dimethoxy-2-nitrophenyl)methoxy]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid
• Synonyms: O-[(4,5-Dimethoxy-2-nitrophenyl)methyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine; N-Fmoc DMNB-L-serine

Database IDs

• CAS Number: 628280-43-3
• PubChem SID: 162263463
• PubChem CID: 12990752

CALCULATED PROPERTIES

• Acid pKa: 2.886637
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 1.4259545
• LogD (pH = 7.4): 0.50404817
• Log P: 3.9906485
• Molar Refractivity: 135.7357 cm^3
• Polarizability: 53.067905 Å^3
• Polar Surface Area: 149.14 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F628850

A photolytically labile serine molecule, able to be incorporated into short peptides to create caged protein kinase sensors, allowing measurement of intracellular enzymatic activity.

REFERENCES

• Nagai, Y., et al.: Nat. Biotechnol., 18, 313 (2000)
• Kurokawa, K., et al.: J. Biol. Chem., 276, 31305 (2000)