(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 ID: 134162
• Molecular Formular: C23H34O5
• Molecular Mass: 390.51306
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: mevastatin
• Synonyms: Compactin; ML-236B; Mevastatin; Compactin, 6-Demethylvevinolin, CS-500, ML-236 B; Mevastatin

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 14.914537
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.6151679
• LogD (pH = 7.4): 3.6151679
• Log P: 3.6151679
• Molar Refractivity: 108.6338 cm^3
• Polarizability: 42.577927 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO: soluble20 mg/mL; ethanol: soluble25 mg/mL
• Apperance: Off-White Solid; white powder
• Melting Point: 135-137°C; 151-153 °C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... HMGCL(3155), HMGCR(3156)rat ... Hmgcr(25675)

Product Information

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

DETAILS

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.

REFERENCES

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