tetralithium(1+) ion 3-hydroxy-3-methyl-5-{[(phosphonatooxy)phosphinato]oxy}pentanoate

• ChemBase ID: 154528
• Molecular Formular: C6H10Li4O10P2
• Molecular Mass: 331.849122
• Monoisotopic Mass: 332.03893798
• SMILES: [Li+].[Li+].[Li+].[Li+].CC(CCOP(=O)([O-])OP(=O)([O-])[O-])(CC(=O)[O-])O
• Canonical SMILES: [O-]C(=O)CC(CCOP(=O)(OP(=O)([O-])[O-])[O-])(O)C.[Li+].[Li+].[Li+].[Li+]
• InChI: InChI=1S/C6H14O10P2.4Li/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12;;;;/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12);;;;/q;4*+1/p-4
• InChIKey: GFIXUUFXTAPBAD-UHFFFAOYSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: tetralithium(1+) ion 3-hydroxy-3-methyl-5-{[(phosphonatooxy)phosphinato]oxy}pentanoate; tetralithium(1+) ion (3R)-3-hydroxy-3-methyl-5-{[(phosphonatooxy)phosphinato]oxy}pentanoate
• IUPAC Traditional name: tetralithium(1+) ion 3-hydroxy-3-methyl-5-[(phosphonatooxyphosphinato)oxy]pentanoate; tetralithium(1+) ion mevalonate 5-diphosphate
• Synonyms: (±)-Mevalonic acid 5-diphosphate tetralithium salt; MVAPP; (±)-Mevalonic acid 5-pyrophosphate tetralithium salt; (R)-Mevalonic acid 5-diphosphate tetralithium salt; R-MVAPP; (R)-Mevalonic acid 5-pyrophosphate tetralithium salt

Database IDs

• CAS Number: 108869-00-7
• MDL Number: MFCD16875407; MFCD16875404
• PubChem SID: 162248667
• PubChem CID: 71311891

CALCULATED PROPERTIES

• Acid pKa: 1.7759297
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -7.402006
• LogD (pH = 7.4): -9.674139
• Log P: -1.6387441
• Molar Refractivity: 63.7292 cm^3
• Polarizability: 22.581154 Å^3
• Polar Surface Area: 182.14 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -2.2±0.5°, c = 0.1 in 0.05 M NaOH

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥80% (qNMR); ≥90% (qNMR)
• Empirical Formula (Hill Notation): C6H10Li4O10P2

DETAILS

Sigma Aldrich - 94259

Biochem/physiol Actions
Metabolite of the mevalonate pathway, which plays a key role in the biosynthesis of sterols, dolichol, heme and ubiquinone. Of interest for research in the disease areas oncology, autoimmune diseases, artherosclerosis and Alzheimer disease, as well as for inherited deficiencies of mevalonate kinase. Mevalonic acid 5-pyrophosphate was shown to elevate ubiquinone levels in rat liver tiβues. 1

Sigma Aldrich - 77631

Biochem/physiol Actions
Metabolite of the mevalonate pathway, which plays a key role in the biosynthesis of sterols, dolichol, heme and ubiquinone. Of interest for research in the disease areas oncology, autoimmune diseases, artherosclerosis and Alzheimer disease, as well as for inherited deficiencies of mevalonate kinase.