3-{[amino({bis[2-chloro(2,2-2H2)ethyl]amino})phosphoryl]oxy}propan-1-ol

• ChemBase ID: 159629
• Molecular Formular: C7H17Cl2N2O3P
• Molecular Mass: 279.101241
• Monoisotopic Mass: 278.0353844
• SMILES: C(OP(=O)(N(CCCl)CCCl)N)CCO
• Canonical SMILES: OCCCOP(=O)(N(CCCl)CCCl)N
• InChI: InChI=1S/C7H17Cl2N2O3P/c8-2-4-11(5-3-9)15(10,13)14-7-1-6-12/h12H,1-7H2,(H2,10,13)
• InChIKey: BZGFIGVSVQRQBJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[amino({bis[2-chloro(2,2-^2H₂)ethyl]amino})phosphoryl]oxy}propan-1-ol
• IUPAC Traditional name: 3-{[amino(bis[2-chloro(2,2-^2H₂)ethyl]amino)phosphoryl]oxy}propan-1-ol
• Synonyms: N,N-Bis(2-chloroethyl)phosphorodiamidic Acid-d4 3-Hydroxypropyl Ester; O-(3-Hydroxypropyl) N,N-Bis(2-chloroethyl)phosphorodiamidate-d4; NSC 153182-d4; NSC 227248-d4; Alcophosphamide-d4

Database IDs

• PubChem SID: 162253764
• PubChem CID: 71313069

CALCULATED PROPERTIES

• Acid pKa: 14.520314
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.64570546
• LogD (pH = 7.4): -0.64570546
• Log P: -0.64570546
• Molar Refractivity: 61.8427 cm^3
• Polarizability: 24.76272 Å^3
• Polar Surface Area: 75.79 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A514577

Labelled Alcophosphamide, a metabolite of the chemotherapeutic agent Cyclophosphamide (C988580).

REFERENCES

• Chan, K. et al.: Cancer Res., 54, 6421 (1994)
• Bates, D.J. et al.: Biochem. Pharmacol., 30, 3055 (1994)
• Joqueviel, C. et al.: Drug Metab. Dispos., 26, 418 (1994)