2-(1-{2-[(3R,5S)-1-[3-(acetyloxy)-2,2-dimethylpropyl]-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl}(2H9)piperidin-4-yl)acetic acid

• ChemBase ID: 172219
• Molecular Formular: C33H41ClN2O9
• Molecular Mass: 645.13964
• Monoisotopic Mass: 644.25005858
• SMILES: C1(=O)N(c2c([C@H](O[C@@H]1CC(=O)N1CCC(CC1)CC(=O)O)c1cccc(c1OC)OC)cc(cc2)Cl)CC(COC(=O)C)(C)C
• Canonical SMILES: COc1cccc(c1OC)[C@H]1O[C@H](CC(=O)N2CCC(CC2)CC(=O)O)C(=O)N(c2c1cc(Cl)cc2)CC(COC(=O)C)(C)C
• InChI: InChI=1S/C33H41ClN2O9/c1-20(37)44-19-33(2,3)18-36-25-10-9-22(34)16-24(25)30(23-7-6-8-26(42-4)31(23)43-5)45-27(32(36)41)17-28(38)35-13-11-21(12-14-35)15-29(39)40/h6-10,16,21,27,30H,11-15,17-19H2,1-5H3,(H,39,40)/t27-,30-/m1/s1
• InChIKey: CMLUGNQVANVZHY-POURPWNDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1-{2-[(3R,5S)-1-[3-(acetyloxy)-2,2-dimethylpropyl]-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl}(^2H₉)piperidin-4-yl)acetic acid
• IUPAC Traditional name: (1-{2-[(3R,5S)-1-[3-(acetyloxy)-2,2-dimethylpropyl]-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-3,5-dihydro-4,1-benzoxazepin-3-yl]acetyl}(^2H₉)piperidin-4-yl)acetic acid
• Synonyms: 1-[2-[(3R,5S)-1-[3-(Acetyloxy)-2,2-dimethylpropyl]-7-chloro-5-(2,3-dimethoxyphenyl)-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepin-3-yl]acetyl]-4-piperidineacetic Acid-d9; (3R-trans)-1-[[1-[3-(acetyloxy)-2,2-dimethylpropyl]-7-chloro-5-(2,3-dimethoxyphenyl)-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepin-3-yl]acetyl]-4-piperidineacetic Acid-d9; TAK 475-d9; Lapaquistat-d9 Acetate

Database IDs

• PubChem SID: 164228129
• PubChem CID: 71749746

CALCULATED PROPERTIES

• Acid pKa: 4.2790923
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 2.0926642
• LogD (pH = 7.4): 0.35868585
• Log P: 3.3368025
• Molar Refractivity: 165.2293 cm^3
• Polarizability: 64.83742 Å^3
• Polar Surface Area: 131.91 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L175502

A novel labelled squalene synthase inhibitor. Lapaquistat acetate decreased plasma cholesterol and triglyceride levels, by lowering lipoproteins containing apoB100. Treatment with Lapaquistat acetate increased collagen concentration and transformed coron

REFERENCES

• Amano, Y., et al.: Eur. J. Pharmacol., 466, 155 ( 2003), Hiyoshi, H., et al.: J. Lipid Res., 44, 128 (2003)
• Miki, T., et al.: J. Med. Chem., 45, 4571 (2003)
• Shiomi, M., et al.: Atherosclerosis, 178, 287 (2003)