(2S)-2-amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid

• ChemBase ID: 3507
• Molecular Formular: C9H10N2O5
• Molecular Mass: 226.1861
• Monoisotopic Mass: 226.05897143
• SMILES: N[C@@H](Cc1ccc(O)c(c1)[N+](=O)[O-])C(=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-nitrophenyl)propanoic acid
• IUPAC Traditional name: nitrotyrosine
• Synonyms: Meta-Nitro-Tyrosine; 3-NITRO-L-TYROSINE; 3-Nitro-L-tyrosine 99%; 3-Nitro-L-tyrosine; H-3-Nitro-Tyr-OH; 3-Nitro-L-tyrosine; 3-Nitrotyrosine; Nitrotyrosine; L-3-Nitrotyrosine; NSC 37413; 3-硝基-L-酪氨酸

Database IDs

• CAS Number: 621-44-3
• EC Number: 210-688-6
• MDL Number: MFCD00007123
• Beilstein Number: 2813157
• PubChem SID: 160966946; 46507718; 24897825; 24886641
• PubChem CID: 65124
• CHEBI ID: 44454
• Chemspider ID: 58633
• DrugBank ID: DB03867
• Wikipedia Title: Nitrotyrosine

CALCULATED PROPERTIES

JChem

• 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: 20.514719 Å^3
• Polar Surface Area: 129.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.07
• LOG S: -2.18
• Solubility (Water): 1.49e+00 g/l

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Yellow Solid; yellow to green crystalline; Yellow to green crystalline solid
• Melting Point: ~230 °C (dec.); 228-230°C; 233°C; 233-235 °C (dec.); 233-235 °C (dec.)(lit.); ca 230°C dec.
• Optical Rotation: [α]20/D +4.5±0.5°, c = 3.2% in 1 M HCl; [α]22/D +3.8°, c = 1 in 1 M HCl

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ~99%; ≥98.0% (NT); 98%; 99%
• Grade: purum
• Linear Formula: O2NC6H3-4-(OH)CH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 05221138

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102460

Purity: ~99%
Yellowish-green crystals

DrugBank - DB03867

Drug information: experimental

Sigma Aldrich - N7389

Application
Marker for peroxynitrite.
Biochem/physiol Actions
Oxidant and cytotoxic agent.
包装
5, 10, 25 g in poly bottle

Sigma Aldrich - 851914

Packaging
25 g in poly bottle

Toronto Research Chemicals - N597000

A 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)