3-(2-chloroethyl)-2-hydroxy-1,3,6,2λ5-oxadiazaphosphonan-2-one

• ChemBase ID: 164231
• Molecular Formular: C7H16ClN2O3P
• Molecular Mass: 242.640301
• Monoisotopic Mass: 242.05870669
• SMILES: O1P(=O)(N(CCNCCC1)CCCl)O
• Canonical SMILES: ClCCN1CCNCCCOP1(=O)O
• InChI: InChI=1S/C7H16ClN2O3P/c8-2-5-10-6-4-9-3-1-7-13-14(10,11)12/h9H,1-7H2,(H,11,12)
• InChIKey: SIMWMEHPUXRDQD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-chloroethyl)-2-hydroxy-1,3,6,2λ^5-oxadiazaphosphonan-2-one
• IUPAC Traditional name: 3-(2-chloroethyl)-2-hydroxy-1,3,6,2λ^5-oxadiazaphosphonan-2-one
• Synonyms: Cyclophosphamide Monochloro Impurity; 3-(2-Chloroethyl)octahydro-2-hydroxy-1,3,6,2-oxadiazaphosphonine 2-Oxide

Database IDs

• CAS Number: 158401-52-6
• PubChem SID: 162258366
• PubChem CID: 3074468

CALCULATED PROPERTIES

• Acid pKa: 2.9277694
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.801002
• LogD (pH = 7.4): -1.8227789
• Log P: -1.8008665
• Molar Refractivity: 55.4271 cm^3
• Polarizability: 21.984756 Å^3
• Polar Surface Area: 61.8 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C366170

A metabolite of Cyclophosphamide (C988580).

REFERENCES

• Joqueviel, C. et al.: Drug Metab. Dispos., 26, 418 (1998)