sodium (3R,5R)-7-[(1S,2S,8S,8aR)-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

• ChemBase ID: 174607
• Molecular Formular: C23H35NaO6
• Molecular Mass: 430.51017
• Monoisotopic Mass: 430.23313312
• SMILES: [C@@H]1(CCC=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)OC(=O)[C@H](CC)C.[Na+]
• Canonical SMILES: CC[C@@H](C(=O)O[C@H]1CCC=C2[C@H]1[C@@H](CC[C@H](C[C@H](CC(=O)[O-])O)O)[C@H](C=C2)C)C.[Na+]
• InChI: InChI=1S/C23H36O6.Na/c1-4-14(2)23(28)29-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-17(24)12-18(25)13-21(26)27;/h6,8-9,14-15,17-20,22,24-25H,4-5,7,10-13H2,1-3H3,(H,26,27);/q;+1/p-1/t14-,15-,17+,18+,19-,20-,22-;/m0./s1
• InChIKey: HSOJKEMXKOVVOH-AGNATJBLSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5R)-7-[(1S,2S,8S,8aR)-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: sodium (3R,5R)-7-[(1S,2S,8S,8aR)-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: (βR,δR,1S,2S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-β,δ-dihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-1-naphthaleneheptanoic Acid Sodium Salt; [1S-[1α(βS*,δS*),2α,8β(R*),8aα]]-1,2,6,7,8,8a-Hexahydro-β,δ-dihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-1-naphthaleneheptanoic Acid Monosodium Salt; (βR,δR,1S,2S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-β,δ-dihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-1-naphthaleneheptanoic Acid Monosodium Salt; ML 236B Sodium Salt; Mevastatin Hydroxy Acid Sodium Salt

Database IDs

• CAS Number: 99782-89-5
• PubChem SID: 164230517
• PubChem CID: 16760562

CALCULATED PROPERTIES

• Acid pKa: 4.212299
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.643644
• LogD (pH = 7.4): -0.07435383
• Log P: 2.9506967
• Molar Refractivity: 122.9631 cm^3
• Polarizability: 43.577713 Å^3
• Polar Surface Area: 106.89 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M340510

An active carboxylate of Mevastatin (M340500). It is a competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase with hypocholesterolemic activity. It has been shown to be effective in reducing cholesterol synthesis in vivo, and thereby in

REFERENCES

• Endo, A. et al.: Atheroscler. Supp., 5, 39 (2004)
• Hosobuchi, M. et al.: J. Ferm. Bioeng., 76, 470 (2004)