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 |
|---|---|---|
| Purification and regulation of mevalonate kinase from rat liver. | 1990 Feb 5 |
|
| Solubilization, purification, and characterization of a truncated form of rat hepatic squalene synthetase. | 1992 Apr 25 |
|
| Natural and synthetic non-peptide antigens recognized by human gamma delta T cells. | 1995 May 11 |
|
| Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways. | 1997 Nov |
|
| Determination of farnesyl pyrophosphate in dog and human plasma by high-performance liquid chromatography with fluorescence detection. | 1997 Oct 1 |
|
| Truncation of human squalene synthase yields active, crystallizable protein. | 1998 Feb 15 |
|
| The basis for K-Ras4B binding specificity to protein farnesyltransferase revealed by 2 A resolution ternary complex structures. | 2000 Feb 15 |
|
| Simvastatin modulates cytokine-mediated endothelial cell adhesion molecule induction: involvement of an inhibitory G protein. | 2000 Sep 1 |
|
| Tissue-specific transcriptional regulation of the cholesterol biosynthetic pathway leads to accumulation of testis meiosis-activating sterol (T-MAS). | 2002 Jan |
|
| A quantitative structure-activity relationship and pharmacophore modeling investigation of aryl-X and heterocyclic bisphosphonates as bone resorption agents. | 2003 Jul 3 |
|
| Simvastatin modulates expression of the PON1 gene and increases serum paraoxonase: a role for sterol regulatory element-binding protein-2. | 2003 Nov 1 |
|
| Transcriptional regulation of farnesyl pyrophosphate synthase by liver X receptors. | 2003 Sep |
|
| Higher farnesyl diphosphate synthase activity in human colorectal cancer inhibition of cellular apoptosis. | 2004 |
|
| Substrate binding mode and reaction mechanism of undecaprenyl pyrophosphate synthase deduced from crystallographic studies. | 2004 Apr |
|
| Staphylococcus aureus mevalonate kinase: isolation and characterization of an enzyme of the isoprenoid biosynthetic pathway. | 2004 Jan |
|
| Differential effects of simvastatin on mesangial cells. | 2004 Jul |
|
| Lysine beta311 of protein geranylgeranyltransferase type I partially replaces magnesium. | 2004 Jul 16 |
|
| Simvastatin augments lipopolysaccharide-induced proinflammatory responses in macrophages by differential regulation of the c-Fos and c-Jun transcription factors. | 2004 Jun 15 |
|
| Lovastatin-induced apoptosis in human melanoma cell lines. | 2005 Apr |
|
| Pyridinium-1-yl bisphosphonates are potent inhibitors of farnesyl diphosphate synthase and bone resorption. | 2005 Apr 21 |
|
| Simvastatin inhibits NOR-1 expression induced by hyperlipemia by interfering with CREB activation. | 2005 Aug 1 |
|
| Interplay of isoprenoid and peptide substrate specificity in protein farnesyltransferase. | 2005 Aug 23 |
|
| Effect of pitavastatin on transactivation of human serum paraoxonase 1 gene. | 2005 Feb |
|
| Regulation of macrophage cholesterol efflux through hydroxymethylglutaryl-CoA reductase inhibition: a role for RhoA in ABCA1-mediated cholesterol efflux. | 2005 Jun 10 |
|
| The crystal structure of human geranylgeranyl pyrophosphate synthase reveals a novel hexameric arrangement and inhibitory product binding. | 2006 Aug 4 |
|
| Digeranyl bisphosphonate inhibits geranylgeranyl pyrophosphate synthase. | 2007 Feb 23 |
|
| Survivin down-regulation plays a crucial role in 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor-induced apoptosis in cancer. | 2007 Jul 6 |
|
| The carboxyl-terminal region of the geranylgeranyl diphosphate synthase is indispensable for the stabilization of the region involved in substrate binding and catalysis. | 2007 Oct |
|
| Simvastatin inhibits central sympathetic outflow in heart failure by a nitric-oxide synthase mechanism. | 2008 Jul |
|
| 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 Mar |
|
| Biochemical and structural basis for feedback inhibition of mevalonate kinase and isoprenoid metabolism. | 2008 Mar 25 |
|
| Simvastatin suppresses LPS-induced MMP-1 expression in U937 mononuclear cells by inhibiting protein isoprenylation-mediated ERK activation. | 2008 Oct |
|
| Statins induce apoptosis in ovarian cancer cells through activation of JNK and enhancement of Bim expression. | 2009 May |
|
| Isopentenyl pyrophosphate is a novel antinociceptive substance that inhibits TRPV3 and TRPA1 ion channels. | 2011 May |
|
| Simvastatin reduces steroidogenesis by inhibiting Cyp17a1 gene expression in rat ovarian theca-interstitial cells. | 2012 Jan |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 20:20:22 GMT 2023
by
admin
on
Sat Dec 16 20:20:22 GMT 2023
|
| Record UNII |
G8X8WT527W
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
G8X8WT527W
Created by
admin on Sat Dec 16 20:20:22 GMT 2023 , Edited by admin on Sat Dec 16 20:20:22 GMT 2023
|
PRIMARY | |||
|
372-97-4
Created by
admin on Sat Dec 16 20:20:22 GMT 2023 , Edited by admin on Sat Dec 16 20:20:22 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
TARGET -> SUBSTRATE |
|
