(2S)-2-amino-3-{4-[(2-nitrophenyl)methoxy]phenyl}propanoic acid

• ChemBase ID: 175203
• Molecular Formular: C16H16N2O5
• Molecular Mass: 316.30864
• Monoisotopic Mass: 316.10592162
• SMILES: c1c(ccc(c1)C[C@H](N)C(=O)O)OCc1ccccc1[N+](=O)[O-]
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(cc1)OCc1ccccc1[N+](=O)[O-])N
• InChI: InChI=1S/C16H16N2O5/c17-14(16(19)20)9-11-5-7-13(8-6-11)23-10-12-3-1-2-4-15(12)18(21)22/h1-8,14H,9-10,17H2,(H,19,20)/t14-/m0/s1
• InChIKey: NLFOHNAFILVHGM-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{4-[(2-nitrophenyl)methoxy]phenyl}propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-{4-[(2-nitrophenyl)methoxy]phenyl}propanoic acid
• Synonyms: O-[(2-Nitrophenyl)methyl]-L-tyrosine Hydrochloride; O-(2-Nitrobenzyl)-L-tyrosine Hydrochloride

Database IDs

• CAS Number: 207727-86-4
• PubChem SID: 164231113
• PubChem CID: 11989621

CALCULATED PROPERTIES

• Acid pKa: 1.8107255
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.3218623
• LogD (pH = 7.4): 0.31849673
• Log P: 0.32181755
• Molar Refractivity: 83.5168 cm^3
• Polarizability: 31.892406 Å^3
• Polar Surface Area: 118.37 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N493700

A novel derivative of Tyrosine used in the synthesis of caged peptides.

REFERENCES

• Adams, P., et al.: J. Membr. Biol., 58, 161 (1981)
• Saks, M., et al.: J. Biol. Chem., 271, 23169 (1981)
• Zhang, H., et al.: Biochemistry, 36, 15856 (1981)