Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H28O7P2 |
| Molecular Weight | 382.3261 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O
InChI
InChIKey=VWFJDQUYCIWHTN-YFVJMOTDSA-N
InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
| Molecular Formula | C15H28O7P2 |
| Molecular Weight | 382.3261 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Optical Activity | NONE |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Simvastatin reduces steroidogenesis by inhibiting Cyp17a1 gene expression in rat ovarian theca-interstitial cells. | 2012-01 |
|
| Isopentenyl pyrophosphate is a novel antinociceptive substance that inhibits TRPV3 and TRPA1 ion channels. | 2011-05 |
|
| Statins induce apoptosis in ovarian cancer cells through activation of JNK and enhancement of Bim expression. | 2009-05 |
|
| Simvastatin inhibits induction of matrix metalloproteinase-9 in rat alveolar macrophages exposed to cigarette smoke extract. | 2009-04-30 |
|
| Simvastatin suppresses LPS-induced MMP-1 expression in U937 mononuclear cells by inhibiting protein isoprenylation-mediated ERK activation. | 2008-10 |
|
| Simvastatin inhibits central sympathetic outflow in heart failure by a nitric-oxide synthase mechanism. | 2008-07 |
|
| Biochemical and structural basis for feedback inhibition of mevalonate kinase and isoprenoid metabolism. | 2008-03-25 |
|
| Simvastatin antagonizes tumor necrosis factor-alpha inhibition of bone morphogenetic proteins-2-induced osteoblast differentiation by regulating Smad signaling and Ras/Rho-mitogen-activated protein kinase pathway. | 2008-03 |
|
| The carboxyl-terminal region of the geranylgeranyl diphosphate synthase is indispensable for the stabilization of the region involved in substrate binding and catalysis. | 2007-10 |
|
| Survivin down-regulation plays a crucial role in 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor-induced apoptosis in cancer. | 2007-07-06 |
|
| Digeranyl bisphosphonate inhibits geranylgeranyl pyrophosphate synthase. | 2007-02-23 |
|
| The crystal structure of human geranylgeranyl pyrophosphate synthase reveals a novel hexameric arrangement and inhibitory product binding. | 2006-08-04 |
|
| Interplay of isoprenoid and peptide substrate specificity in protein farnesyltransferase. | 2005-08-23 |
|
| Simvastatin inhibits NOR-1 expression induced by hyperlipemia by interfering with CREB activation. | 2005-08-01 |
|
| Regulation of macrophage cholesterol efflux through hydroxymethylglutaryl-CoA reductase inhibition: a role for RhoA in ABCA1-mediated cholesterol efflux. | 2005-06-10 |
|
| Pyridinium-1-yl bisphosphonates are potent inhibitors of farnesyl diphosphate synthase and bone resorption. | 2005-04-21 |
|
| Lovastatin-induced apoptosis in human melanoma cell lines. | 2005-04 |
|
| Effect of pitavastatin on transactivation of human serum paraoxonase 1 gene. | 2005-02 |
|
| Lysine beta311 of protein geranylgeranyltransferase type I partially replaces magnesium. | 2004-07-16 |
|
| Differential effects of simvastatin on mesangial cells. | 2004-07 |
|
| Simvastatin augments lipopolysaccharide-induced proinflammatory responses in macrophages by differential regulation of the c-Fos and c-Jun transcription factors. | 2004-06-15 |
|
| Substrate binding mode and reaction mechanism of undecaprenyl pyrophosphate synthase deduced from crystallographic studies. | 2004-04 |
|
| Staphylococcus aureus mevalonate kinase: isolation and characterization of an enzyme of the isoprenoid biosynthetic pathway. | 2004-01 |
|
| Higher farnesyl diphosphate synthase activity in human colorectal cancer inhibition of cellular apoptosis. | 2004 |
|
| Simvastatin modulates expression of the PON1 gene and increases serum paraoxonase: a role for sterol regulatory element-binding protein-2. | 2003-11-01 |
|
| Transcriptional regulation of farnesyl pyrophosphate synthase by liver X receptors. | 2003-09 |
|
| A quantitative structure-activity relationship and pharmacophore modeling investigation of aryl-X and heterocyclic bisphosphonates as bone resorption agents. | 2003-07-03 |
|
| Tissue-specific transcriptional regulation of the cholesterol biosynthetic pathway leads to accumulation of testis meiosis-activating sterol (T-MAS). | 2002-01 |
|
| Simvastatin modulates cytokine-mediated endothelial cell adhesion molecule induction: involvement of an inhibitory G protein. | 2000-09-01 |
|
| The basis for K-Ras4B binding specificity to protein farnesyltransferase revealed by 2 A resolution ternary complex structures. | 2000-02-15 |
|
| Truncation of human squalene synthase yields active, crystallizable protein. | 1998-02-15 |
|
| Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways. | 1997-11 |
|
| Determination of farnesyl pyrophosphate in dog and human plasma by high-performance liquid chromatography with fluorescence detection. | 1997-10-01 |
|
| Natural and synthetic non-peptide antigens recognized by human gamma delta T cells. | 1995-05-11 |
|
| Solubilization, purification, and characterization of a truncated form of rat hepatic squalene synthetase. | 1992-04-25 |
|
| Purification and regulation of mevalonate kinase from rat liver. | 1990-02-05 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 19:22:40 GMT 2025
by
admin
on
Wed Apr 02 19:22:40 GMT 2025
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| Record UNII |
G8X8WT527W
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Validated (UNII)
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17407
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G8X8WT527W
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79W6B01D07
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FARNESYL PYROPHOSPHATE
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DB07780
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13058-04-3
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DTXSID701020624
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50277
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372-97-4
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445713
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