ammonium (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

• ChemBase ID: 177772
• Molecular Formular: C25H43NO6
• Molecular Mass: 453.61202
• Monoisotopic Mass: 453.3090381
• SMILES: [C@@H]1(C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)C)OC(=O)C(CC)(C)C.[NH4+]
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@H](C[C@H](CC(=O)[O-])O)O)[C@H](C=C2)C)(C)C.[NH4+]
• InChI: InChI=1S/C25H40O6.H3N/c1-6-25(4,5)24(30)31-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-18(26)13-19(27)14-22(28)29;/h7-8,11,15-16,18-21,23,26-27H,6,9-10,12-14H2,1-5H3,(H,28,29);1H3/t15-,16-,18+,19+,20-,21-,23-;/m0./s1
• InChIKey: FFPDWNBTEIXJJF-OKDJMAGBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ammonium (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: ammonium (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: (βR,δR,1S,2S,6R,8S,8aR)-8-(2,2-Dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-β,δ-dihydroxy-2,6-dimethyl-1-naphthaleneheptanoic Acid Ammonium Salt; Simvastatin Acid Ammonium Salt; Simvastatin Ammonium Salt; Simvastatin Carboxylic Acid Ammonium Salt; Simvastatin Hydroxy Acid Ammonium Salt; (3S,5S)-8-(2,2-Dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-β,δ-dihydroxy-2,6-dimethyl-1-naphthaleneheptanoic Acid Ammonium Salt; (3S,5S)-Simvastatin Hydroxy Acid Ammonium Salt

Database IDs

• CAS Number: 139893-43-9
• PubChem SID: 164233682
• PubChem CID: 10961424

CALCULATED PROPERTIES

• Acid pKa: 4.212299
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.4866774
• LogD (pH = 7.4): 0.76867956
• Log P: 3.79373
• Molar Refractivity: 132.0127 cm^3
• Polarizability: 47.25198 Å^3
• Polar Surface Area: 106.89 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol; Water
• Apperance: White Solid
• Melting Point: 128-131°C

Safety Information

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

DETAILS

Toronto Research Chemicals - S485025

A metabolite of Simvastin (S485000). A competitive inhibitor of HMG-CoA reductase.

Toronto Research Chemicals - S485020

A metabolite of Simvastin (S485000). A competitive inhibitor of HMG-CoA reductase.

REFERENCES

• Hoffman, W.F., et al.: J. Med. Chem., 29, 849 (1986)
• Mol, M.J., et al.: Lancet, 2, 936 (1986)
• Hoffman, W.F., et al.: J. Med. Chem., 29, 849 (1986)
• Mol, M.J., et al.: Lancet, 2, 936 (1986)