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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 376807923 |
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| ImageFile = Farnesyl_pyrophosphate.png |
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| verifiedrevid = 424660305 |
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| ImageSize = 220px |
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| ImageFile = Farnesylpyrophosphat Strukturformel V2a.svg |
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| ImageName = Skeletal formula |
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| ImageSize = 220px |
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| ImageFile1 = Farnesyl-pyrophosphate-3D-balls.png |
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| ImageName = Skeletal formula |
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| ImageSize1 = 250px |
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| ImageFile1 = Farnesyl-pyrophosphate-3D-balls.png |
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| ImageName1 = Ball-and-stick model |
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| ImageSize1 = 250px |
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| IUPACName = |
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| ImageName1 = Ball-and-stick model |
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| OtherNames = |
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| PIN = (2''E'',6''E'')-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo=13058-04-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem=706 |
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| CASNo= 372-97-4 |
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| SMILES= |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| MeSHName=farnesyl+pyrophosphate |
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| UNII = G8X8WT527W |
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| PubChem=445713 |
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|Section2= {{Chembox Properties |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Formula=C<sub>15</sub>H<sub>28</sub>O<sub>7</sub>P<sub>2</sub> |
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| ChemSpiderID = 393270 |
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| MolarMass=382.326 |
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| SMILES=CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)C |
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| Appearance= |
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| 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+ |
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| Density= |
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| InChIKey=VWFJDQUYCIWHTN-YFVJMOTDSA-N |
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| MeltingPt= |
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| MeSHName=farnesyl+pyrophosphate |
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| BoilingPt= |
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| Solubility= |
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|Section2={{Chembox Properties |
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| C=15 | H=28 | O=7 | P=2 |
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|Section3= {{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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'''Farnesyl pyrophosphate''' (FPP) is an intermediate in the ] used by organisms in the biosynthesis of ]s, ]s, and ]s. |
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'''Farnesyl pyrophosphate''' ('''FPP'''), also known as '''farnesyl diphosphate''' ('''FDP'''), is the precursor to all ]s, which comprises thousand of compounds.<ref name=KO>{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }}</ref> These include all ]s as well as ] and ].<ref>{{cite journal|title=Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes| vauthors = Davis EM, Croteau R |s2cid=53419212|journal=Topics in Current Chemistry |year=2000 |volume=209 |pages=53–95 |doi=10.1007/3-540-48146-X_2 |isbn=978-3-540-66573-1}}</ref> It is also used in the synthesis of ] (part of the electron transport chain), as well as dehydrodolichol diphosphate (a precursor of ], which transports proteins to the ] for ]). |
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It is the immediate precursor of ] (via the enzyme ]), dehydrodolichol diphosphate (a precursor of ]), and ] (GGPP). |
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==Biosynthesis== |
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==Biosynthesis== |
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] (a ]) catalyzes sequential condensation reactions of ] with 2 units of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate. |
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] (a ])<ref>{{cite journal | vauthors = Kulkarni RS, Pandit SS, Chidley HG, Nagel R, Schmidt A, Gershenzon J, Pujari KH, Giri AP, Gupta VS | display-authors = 6 |title=Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit |journal=Plant Physiology and Biochemistry |date=October 2013 |volume=71 |pages=121–131 |doi=10.1016/j.plaphy.2013.07.006| pmid = 23911730 }}</ref> catalyzes sequential condensation reactions of ] with 2 units of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate: |
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:]{{clear-left}} |
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==Pharmacology== |
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* Dimethylallyl pyrophosphate reacts with 3-isopentenyl pyrophosphate to form ]: |
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The above reactions are inhibited by ]s (used for ]).<ref>{{cite journal | vauthors = Russell RG | title = Bisphosphonates: from bench to bedside | journal = Annals of the New York Academy of Sciences | volume = 1068 | issue = April 2006 | pages = 367–401 | date = April 2006 | pmid = 16831938 | doi = 10.1196/annals.1346.041 | s2cid = 20706956 | bibcode = 2006NYASA1068..367R }}</ref> Farnesyl pyrophosphate is a ] of ].<ref name="pmid20395302">{{cite journal | vauthors = Bang S, Yoo S, Yang TJ, Cho H, Hwang SW | title = Farnesyl pyrophosphate is a novel pain-producing molecule via specific activation of TRPV3 | journal = The Journal of Biological Chemistry | volume = 285 | issue = 25 | pages = 19362–71 | date = June 2010 | pmid = 20395302 | pmc = 2885216 | doi = 10.1074/jbc.M109.087742 | doi-access = free }}</ref> |
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* Geranyl pyrophosphate itself reacts with 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate |
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] |
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==Regulation== |
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The above reactions are inhibited by ]s (used for ]). |
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==Related compounds== |
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==Related compounds== |
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== References == |
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{{Reflist}} |
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{{Cholesterol metabolism intermediates}} |
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{{Cholesterol metabolism intermediates}} |
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{{DEFAULTSORT:Farnesyl Pyrophosphate}} |
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{{DEFAULTSORT:Farnesyl Pyrophosphate}} |
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{{Biochem-stub}} |
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