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

• ChemBase ID: 171153
• Molecular Formular: C23H35NaO7
• Molecular Mass: 446.50957
• Monoisotopic Mass: 446.22804774
• SMILES: C1C=CC2=C[C@@H]([C@@H]([C@@H]([C@H]2[C@H]1OC(=O)[C@H](CC)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)C)O.[Na+]
• Canonical SMILES: CC[C@@H](C(=O)O[C@H]1CC=CC2=C[C@@H]([C@@H]([C@@H]([C@@H]12)CC[C@H](C[C@H](CC(=O)[O-])O)O)C)O)C.[Na+]
• InChI: InChI=1S/C23H36O7.Na/c1-4-13(2)23(29)30-20-7-5-6-15-10-19(26)14(3)18(22(15)20)9-8-16(24)11-17(25)12-21(27)28;/h5-6,10,13-14,16-20,22,24-26H,4,7-9,11-12H2,1-3H3,(H,27,28);/q;+1/p-1/t13-,14+,16+,17+,18-,19-,20-,22-;/m0./s1
• InChIKey: QMLCOLOJNAKCFF-TWYLDBRHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5R)-7-[(1S,2R,3R,8S,8aR)-3-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,3,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: sodium (3R,5R)-7-[(1S,2R,3R,8S,8aR)-3-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,3,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: 3β-iso-Pravastatin Sodium Salt; [1S-[1α(βS*,δS*),2α,3α,8β(R*),8aα]]-1,2,3,7,8,8a-Hexahydro-β,δ,3-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-1-naphthaleneheptanoic Acid; 3β-Hydroxy Pravastatin Sodium Salt

Database IDs

• PubChem SID: 164227063
• PubChem CID: 23695788

CALCULATED PROPERTIES

• Acid pKa: 4.169863
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.45059016
• LogD (pH = 7.4): -1.2558957
• Log P: 1.7978394
• Molar Refractivity: 124.4016 cm^3
• Polarizability: 44.225346 Å^3
• Polar Surface Area: 127.12 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water

DETAILS

Toronto Research Chemicals - H952315

A metabolite of Pravastatin, a competitive inhibitor of HMG-CoA reductase. Bioactive metabolite of Mevastatin.

REFERENCES

• Serizawa, N., et al.: J. Antibiot., 36, 604 (1983)
• White, H.D, et al.: N. Engl. J. Med., 343, 317 (2000)