(4S,4aR,5S,6S)-4-[(2,2-dimethylbutanoyl)oxy]-5-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-6-methyl-3,4,4a,5,6,7-hexahydronaphthalene-2-carboxylic acid

• ChemBase ID: 163718
• Molecular Formular: C25H36O7
• Molecular Mass: 448.54914
• Monoisotopic Mass: 448.24610349
• SMILES: [C@@H]1([C@H](CC=C2[C@@H]1[C@H](CC(=C2)C(=O)O)OC(=O)C(CC)(C)C)C)CC[C@@H]1C[C@H](CC(=O)O1)O
• Canonical SMILES: CCC(C(=O)O[C@H]1CC(=CC2=CC[C@@H]([C@@H]([C@@H]12)CC[C@@H]1C[C@@H](O)CC(=O)O1)C)C(=O)O)(C)C
• InChI: InChI=1S/C25H36O7/c1-5-25(3,4)24(30)32-20-11-16(23(28)29)10-15-7-6-14(2)19(22(15)20)9-8-18-12-17(26)13-21(27)31-18/h7,10,14,17-20,22,26H,5-6,8-9,11-13H2,1-4H3,(H,28,29)/t14-,17+,18+,19-,20-,22-/m0/s1
• InChIKey: CGKWQIRKHPKYEV-BPTCXLADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aR,5S,6S)-4-[(2,2-dimethylbutanoyl)oxy]-5-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-6-methyl-3,4,4a,5,6,7-hexahydronaphthalene-2-carboxylic acid
• IUPAC Traditional name: (4S,4aR,5S,6S)-4-[(2,2-dimethylbutanoyl)oxy]-5-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-6-methyl-3,4,4a,5,6,7-hexahydronaphthalene-2-carboxylic acid
• Synonyms: 3-[[Amino[bis(2-chloroethyl)amino]phosphinyl]oxy]propanoic Acid-d4; N,N-Bis(2-chloroethyl)phosphorodiamidate Hydracrylic Acid-d4; Asta 5754-d4; Carboxycyclophosphamide-d4; NSC 145124-d4; Carboxyphosphamide-d4; [4S-[4α,4aβ,5β(2S*,4S*),6β]]-4-(2,2-Dimethyl-1-oxobutoxy)-3,4,4a,5,6,7-hexahydro-6-methyl-5-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-2-naphthalenecarboxylic Acid; 6-Carboxy Δ-5',4',5,6-Simvastatin

Database IDs

• CAS Number: 125206-31-7
• PubChem SID: 162257853
• PubChem CID: 14652873

CALCULATED PROPERTIES

• Acid pKa: 4.589892
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.6467917
• LogD (pH = 7.4): 0.8713047
• Log P: 3.606236
• Molar Refractivity: 119.134 cm^3
• Polarizability: 46.816006 Å^3
• Polar Surface Area: 110.13 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 107-109°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C181352

A labelled metabolite of Cyclophosphamide (CPA) (C988580).

Toronto Research Chemicals - C182405

An intermediate used in the preparation of HMG-CoA reductase inhibitors.

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)