(2S,4R)-4-hydroxy-1-nitrosopyrrolidine-2-carboxylic acid

• ChemBase ID: 175473
• Molecular Formular: C5H8N2O4
• Molecular Mass: 160.12802
• Monoisotopic Mass: 160.04840675
• SMILES: [C@H]1(C[C@H](N(C1)N=O)C(=O)O)O
• Canonical SMILES: O=NN1C[C@@H](C[C@H]1C(=O)O)O
• InChI: InChI=1S/C5H8N2O4/c8-3-1-4(5(9)10)7(2-3)6-11/h3-4,8H,1-2H2,(H,9,10)/t3-,4+/m1/s1
• InChIKey: ABVBOWJCKJGCJM-DMTCNVIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-4-hydroxy-1-nitrosopyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S,4R)-4-hydroxy-1-nitrosopyrrolidine-2-carboxylic acid
• Synonyms: (4R)-4-Hydroxy-1-nitroso-L-proline; N-Nitroso-4-hydroxyproline; N-Nitrosohydroxyproline; N-Nitroso-L-hydroxyproline

Database IDs

• CAS Number: 30310-80-6
• PubChem SID: 164231383
• PubChem CID: 61873

CALCULATED PROPERTIES

• Acid pKa: 3.5757172
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -3.0118916
• LogD (pH = 7.4): -4.390781
• Log P: -1.1687039
• Molar Refractivity: 34.7393 cm^3
• Polarizability: 13.1061 Å^3
• Polar Surface Area: 90.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Water
• Apperance: Tan Solid
• Melting Point: 129-131°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N528600

A carcinogenic nitrosamine; N-nitrosoamino acid derivative found in cured meat products.

REFERENCES

• Kallistratos, G., et al.: J. Med. Sci., et al.: 1, 49 (1983)
• Dennis, M.J., et al.: Food Chem. Toxicol., 22, 305 (1983)