1-nitrosopiperidine-2-carboxylic acid

• ChemBase ID: 175503
• Molecular Formular: C6H10N2O3
• Molecular Mass: 158.1552
• Monoisotopic Mass: 158.06914219
• SMILES: C1CCN(C(C1)C(=O)O)N=O
• Canonical SMILES: O=NN1CCCCC1C(=O)O
• InChI: InChI=1S/C6H10N2O3/c9-6(10)5-3-1-2-4-8(5)7-11/h5H,1-4H2,(H,9,10)
• InChIKey: DSGKTUVITPQPRT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-nitrosopiperidine-2-carboxylic acid
• IUPAC Traditional name: pipecolic acid, 1-nitroso-
• Synonyms: 1-Nitroso-2-piperidinecarboxylic Acid; 1-Nitrosopipecolic Acid; NSC 109550; N-Nitroso-D,L-pipecolic Acid; NPIPAC; N-Nitrosopiperidine-2-carboxylic Acid

Database IDs

• CAS Number: 4515-18-8
• PubChem SID: 164231413
• PubChem CID: 20614

CALCULATED PROPERTIES

• Acid pKa: 3.8670197
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.1069955
• LogD (pH = 7.4): -2.6754997
• Log P: 0.48107406
• Molar Refractivity: 38.0224 cm^3
• Polarizability: 14.189364 Å^3
• Polar Surface Area: 69.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 89-90°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N545225

A volatile mutagen found in cigarette smoke.

REFERENCES

• Lijinsky, W., et al.: Tetrahedron, 26, 5137 (1970)
• Venkatesan, A., et al.: J. Med. Chem., 49, 4623 (1970)
• Helguera, A., et al.: Toxicol. App. Pharmacol., 231, 197 (1970)