(1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate

• ChemBase编号: 134162
• 分子式: C23H34O5
• 平均质量: 390.51306
• 单一同位素质量: 390.24062419
• SMILES: CC[C@H](C)C(=O)O[C@H]1CCC=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]1C[C@H](CC(=O)O1)O
• Canonical SMILES: CC[C@@H](C(=O)O[C@H]1CCC=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
• InChI: InChI=1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1
• InChIKey: AJLFOPYRIVGYMJ-INTXDZFKSA-N

名称和登记号

名称

• IUPAC标准名: (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
• IUPAC传统名: mevastatin
• 别名: Compactin; ML-236B; Mevastatin; Compactin, 6-Demethylvevinolin, CS-500, ML-236 B; Mevastatin

登记号

• CAS号: 73573-88-3
• MDL号: MFCD05662341
• Beilstein号: 1269441
• PubChem SID: 162228439; 24278540
• PubChem CID: 64715

理论计算性质

• Acid pKa: 14.914537
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 3.6151679
• LogD (pH = 7.4): 3.6151679
• Log P: 3.6151679
• 摩尔折射率: 108.6338 cm^3
• 极化性: 42.577927 Å^3
• 极化表面积: 72.83 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Acetone; DMSO: soluble20 mg/mL; ethanol: soluble25 mg/mL
• 外观: Off-White Solid; white powder
• 熔点: 135-137°C; 151-153 °C

安全信息

• 保存条件: -20°C Freezer
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... HMGCL(3155), HMGCR(3156)rat ... Hmgcr(25675)

产品相关信息

• 纯度: ≥95% (HPLC); ≥96% (HPLC)
• Empirical Formula (Hill Notation): C23H34O5

详细说明

Sigma Aldrich - M2537

Biochem/physiol Actions
HMG-CoA reductase inhibitor. Cholesterol lowering drug. Inhibits myoblast formation. An antibiotic shown to cause apoptosis, apparently by inhibiting post-translational prenylation of proteins such as Ras. Similarly, mevastatin increases eNOS mRNA and protein levels by blocking the geranylgeranylation of Rho.

Sigma Aldrich - 27696

Other Notes
Potent inhibitor of 3-hydroxy-3-methylglutaryl-CoA reductase, HMG-CoA reductase1,2,3; Used e.g. in culturing compactin-resistant cell lines overaccumulating HMG-CoA reductase4

Toronto Research Chemicals - M340500

A fungal metabolite which is a potent inhibitor of HMG-CoA reductase.

参考文献

• Endo, A., et al.: FEBS Letters, 72, 323 (1976)
• Endo, A.: J. Med. Chem., 28, 401 (1985)