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(RS)-mevalonate   Click here for help

GtoPdb Ligand ID: 3056

Synonyms: DL-mevalonate | DL-mevalonic acid
Compound class: Metabolite
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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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]