(2S)-2-amino-3-[hydroxy(nitroso)amino]propanoic acid

• ChemBase ID: 159612
• Molecular Formular: C3H7N3O4
• Molecular Mass: 149.10538
• Monoisotopic Mass: 149.04365572
• SMILES: ON(C[C@H](N)C(=O)O)N=O
• Canonical SMILES: O=NN(C[C@@H](C(=O)O)N)O
• InChI: InChI=1S/C3H7N3O4/c4-2(3(7)8)1-6(10)5-9/h2,10H,1,4H2,(H,7,8)/t2-/m0/s1
• InChIKey: MLFKVJCWGUZWNV-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[hydroxy(nitroso)amino]propanoic acid
• IUPAC Traditional name: alanosine
• Synonyms: 3-(Hydroxynitrosoamino)-L-alanine; L-2-Amino-3-(N-nitroso)hydroxylaminopropionic Acid; Alanosine; NSC 153353; NSC 529469; SDX 102; L-Alanosine

Database IDs

• CAS Number: 5854-93-3
• PubChem SID: 162253747
• PubChem CID: 22128

CALCULATED PROPERTIES

• Acid pKa: 1.4996141
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -3.557692
• LogD (pH = 7.4): -3.5788004
• Log P: -3.5575805
• Molar Refractivity: 30.6981 cm^3
• Polarizability: 11.728468 Å^3
• Polar Surface Area: 116.22 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1N HCl; 1N NaOH
• Apperance: Off-White Solid
• Melting Point: 190°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A510810

Antibiotic substance from the fermentation of Streptomyces alanosinicus. The first natural product found to have a N-nitrosohydroxylamino group on an aliphatic chain. An experimental insect reproduction inhibitor.

REFERENCES

• Murthy, et al.: Nature, 211 1198 (1966)
• Thiemann, B., et al.: J. Antibiot., 19A, 155 (1966)
• Gale, et al.: Biochem, Pharmacol., 17, 363 (1966)
• Kenaga, E.E., et al.: J. Econ. Entomol., 62, 1006 (1966)
• Matsumoto, S., et al.: Agric. Biol. Chem., 48, 827 (