geranyl diphosphate   Click here for help

GtoPdb Ligand ID: 3051

Synonyms: geranyl pyrophosphate | GPP | neryl pyrophosphate
PDB Ligand
Compound class: Metabolite
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 132.91
Molecular weight 314.07
XLogP 0.07
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC(=CCOP(=O)(OP(=O)(O)O)O)CCC=C(C)C
Isomeric SMILES C/C(=C\COP(=O)(OP(=O)(O)O)O)/CCC=C(C)C
InChI InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+
InChI Key GVVPGTZRZFNKDS-JXMROGBWSA-N
References
1. Barnard GF, Popják G. (1981)
Human liver prenyltransferase and its characterization.
Biochim Biophys Acta, 661 (1): 87-99. [PMID:7295734]
2. Glickman JF, Schmid A. (2007)
Farnesyl pyrophosphate synthase: real-time kinetics and inhibition by nitrogen-containing bisphosphonates in a scintillation assay.
Assay Drug Dev Technol, 5 (2): 205-14. [PMID:17477829]
3. 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]
4. Qiu Y, Li D. (2006)
Bifunctional inhibitors of mevalonate kinase and mevalonate 5-diphosphate decarboxylase.
Org Lett, 8 (6): 1013-6. [PMID:16524256]
5. Qiu Y, Li D. (2006)
Inhibition of mevalonate 5-diphosphate decarboxylase by fluorinated substrate analogs.
Biochim Biophys Acta, 1760 (7): 1080-7. [PMID:16626865]
6. Runquist M, Ericsson J, Thelin A, Chojnacki T, Dallner G. (1994)
Isoprenoid biosynthesis in rat liver mitochondria. Studies on farnesyl pyrophosphate synthase and trans-prenyltransferase.
J Biol Chem, 269 (8): 5804-9. [PMID:8119922]