(2S)-2-amino-3-[4-hydroxy-3-nitro(2H3)phenyl]propanoic acid

• ChemBase ID: 175537
• Molecular Formular: C9H10N2O5
• Molecular Mass: 226.1861
• Monoisotopic Mass: 226.05897143
• SMILES: c1(c(ccc(c1)C[C@H](N)C(=O)O)O)[N+](=O)[O-]
• Canonical SMILES: OC(=O)[C@H](Cc1ccc(c(c1)[N+](=O)[O-])O)N
• InChI: InChI=1S/C9H10N2O5/c10-6(9(13)14)3-5-1-2-8(12)7(4-5)11(15)16/h1-2,4,6,12H,3,10H2,(H,13,14)/t6-/m0/s1
• InChIKey: FBTSQILOGYXGMD-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[4-hydroxy-3-nitro(^2H₃)phenyl]propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-[4-hydroxy-3-nitro(^2H₃)phenyl]propanoic acid
• Synonyms: L-3-Nitrotyrosine-d3; NSC 37413-d3; 3-Nitro-L-tyrosine-d3

Database IDs

• PubChem SID: 164231447
• PubChem CID: 10846994

CALCULATED PROPERTIES

• Acid pKa: 0.95839024
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.6069049
• LogD (pH = 7.4): -2.6061292
• Log P: -1.550771
• Molar Refractivity: 54.4219 cm^3
• Polarizability: 20.534721 Å^3
• Polar Surface Area: 129.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Yellow Solid
• Melting Point: >217°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - N597002

A labelled marker for peroxynitrite. Oxidant and cytotoxic agent.

REFERENCES

• Sekiguchi, M., et al.: Brain Res., 978, 228 (2003)
• van den Tweel, E., et al.: J. Neurobiol., 167, 64 (2003)
• Shirakura, T., et al.: Biol. Pharm. Bull., 28, 1658 (2003)