3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid

• ChemBase ID: 163717
• Molecular Formular: C7H15Cl2N2O4P
• Molecular Mass: 293.084761
• Monoisotopic Mass: 292.01464896
• SMILES: C(OP(=O)(N(CCCl)CCCl)N)CC(=O)O
• Canonical SMILES: ClCCN(P(=O)(OCCC(=O)O)N)CCCl
• InChI: InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(10,14)15-6-1-7(12)13/h1-6H2,(H2,10,14)(H,12,13)
• InChIKey: QLAKAJLYYGOZQL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid
• IUPAC Traditional name: carboxyphosphamide
• Synonyms: 3-[[Amino[bis(2-chloroethyl)amino]phosphinyl]oxy]propanoic Acid; N,N-Bis(2-chloroethyl)phosphorodiamidate Hydracrylic Acid; Asta 5754; Carboxycyclophosphamide; NSC 145124; Carboxyphosphamide

Database IDs

• CAS Number: 22788-18-7
• PubChem SID: 162257852
• PubChem CID: 31515

CALCULATED PROPERTIES

• Acid pKa: 4.4929156
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.3471024
• LogD (pH = 7.4): -3.1152682
• Log P: -0.30056712
• Molar Refractivity: 61.469 cm^3
• Polarizability: 24.787197 Å^3
• Polar Surface Area: 92.86 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 105-108°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C181350

A metabolite of Cyclophosphamide (CPA) (C988580).

REFERENCES

• Takamizawa, A., et al.: J. Med. Chem., 18, 376 (1975)
• Jones, R.J., et al.: J. Hematother., 1, 343 (1975)
• Biggs, D., et al.: Prog. Clin. Biol. Res., 389, 9 (1975)