lithium(1+) ion (3R)-3,5-dihydroxy-3-methylpentanoate

• ChemBase ID: 154631
• Molecular Formular: C6H11LiO4
• Molecular Mass: 154.09014
• Monoisotopic Mass: 154.08173838
• SMILES: [Li+].CC(CCO)(CC(=O)[O-])O
• Canonical SMILES: OCCC(CC(=O)[O-])(O)C.[Li+]
• InChI: InChI=1S/C6H12O4.Li/c1-6(10,2-3-7)4-5(8)9;/h7,10H,2-4H2,1H3,(H,8,9);/q;+1/p-1/t6-;/m1./s1
• InChIKey: PVWNXFFXFNEHDZ-FYZOBXCZSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: lithium(1+) ion (3R)-3,5-dihydroxy-3-methylpentanoate
• IUPAC Traditional name: lithium(1+) ion (R)-mevalonate
• Synonyms: Lithium (R)-3,5-dihydroxy-3-methylpentanoate; Lithium (R)-3,5-dihydroxy-3-methylvalerate; (R)-Mevalonic acid lithium salt

Database IDs

• MDL Number: MFCD18632545
• PubChem SID: 162248769
• PubChem CID: 55296253

CALCULATED PROPERTIES

• Acid pKa: 4.384681
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.2391148
• LogD (pH = 7.4): -3.993144
• Log P: -1.0933796
• Molar Refractivity: 45.3485 cm^3
• Polarizability: 13.548565 Å^3
• Polar Surface Area: 80.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -22.0±3.0°, c = 0.1 in 1 M HCl (3 h)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥93.0% (qNMR)
• Empirical Formula (Hill Notation): C6H11LiO4

DETAILS

Sigma Aldrich - 50838

Biochem/physiol Actions
Mevalonic acid1,2, is an intermediate in the mevalonate pathway, producing terpenes and steroids. This function provides treatment options metabolic disorders3,4,5,6,7,8, R-mevalonate accumulates in patients with the autosomal recessively inherited mevalonic acidurias, an inborn error of cholesterol and nonsterol isoprene biosynthesis9.