(RS)-mevalonate   

GtoPdb Ligand ID: 3056

Synonyms: DL-mevalonate | DL-mevalonic acid
Comment: (RS)-mevalonate is a mixture of two chiral isoforms, (R)-mevalonate and (S)-mevalonate. Only the (R)-form is biologically active.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 77.76
Molecular weight 148.07
XLogP -0.86
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OCCC(CC(=O)O)(O)C
Isomeric SMILES OCCC(CC(=O)O)(O)C
InChI InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)
InChI Key KJTLQQUUPVSXIM-UHFFFAOYSA-N
References
1. Chu X, Li D. (2003)
Cloning, expression, and purification of His-tagged rat mevalonate kinase.
Protein Expr. Purif., 27 (1): 165-70. [PMID:12509999]
2. Chu X, Li D. (2003)
Expression, purification, and characterization of His20 mutants of rat mevalonate kinase.
Protein Expr. Purif., 32 (1): 75-82. [PMID:14680942]
3. Chu X, Yu W, Wu L, Liu X, Li N, Li D. (2007)
Effect of a disulfide bond on mevalonate kinase.
Biochim. Biophys. Acta, 1774 (12): 1571-81. [PMID:17964869]
4. Fu Z, Voynova NE, Herdendorf TJ, Miziorko HM, Kim JJ. (2008)
Biochemical and structural basis for feedback inhibition of mevalonate kinase and isoprenoid metabolism.
Biochemistry, 47 (12): 3715-24. [PMID:18302342]
5. Hinson DD, Chambliss KL, Toth MJ, Tanaka RD, Gibson KM. (1997)
Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways.
J. Lipid Res., 38 (11): 2216-23. [PMID:9392419]
6. Potter D, Miziorko HM. (1997)
Identification of catalytic residues in human mevalonate kinase.
J. Biol. Chem., 272 (41): 25449-54. [PMID:9325256]
7. Potter D, Wojnar JM, Narasimhan C, Miziorko HM. (1997)
Identification and functional characterization of an active-site lysine in mevalonate kinase.
J. Biol. Chem., 272 (9): 5741-6. [PMID:9038186]
8. Tanaka RD, Schafer BL, Lee LY, Freudenberger JS, Mosley ST. (1990)
Purification and regulation of mevalonate kinase from rat liver.
J. Biol. Chem., 265 (4): 2391-8. [PMID:2153681]