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Farnesyl pyrophosphate information


Farnesyl pyrophosphate
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate
Identifiers
CAS Number
  • 13058-04-3 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 393270 ☒N
MeSH farnesyl+pyrophosphate
PubChem CID
  • 445713
UNII
  • 79W6B01D07 checkY
CompTox Dashboard (EPA)
  • DTXSID701020624 Edit this at Wikidata
InChI
  • 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+
    Key: VWFJDQUYCIWHTN-YFVJMOTDSA-N
SMILES
  • CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)C
Properties
Chemical formula
C15H28O7P2
Molar mass 382.330 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in the biosynthesis of terpenes and terpenoids such as sterols and carotenoids.[1] It is also used in the synthesis of CoQ (part of the electron transport chain), as well as dehydrodolichol diphosphate (a precursor of dolichol, which transports proteins to the ER lumen for N-glycosylation).

  1. ^ Davis EM, Croteau R (2000). "Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes". Topics in Current Chemistry. 209: 53–95. doi:10.1007/3-540-48146-X_2. ISBN 978-3-540-66573-1. S2CID 53419212.

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Farnesyl pyrophosphate

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Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in the biosynthesis of terpenes and terpenoids such as sterols...

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Farnesyl pyrophosphate cyclase

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Farnesyl pyrophosphate cyclase may refer to: 5-epiaristolochene synthase, an enzyme (+)-epicubenol synthase, an enzyme This set index page lists enzyme...

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Geranylgeranyl pyrophosphate

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formed from farnesyl pyrophosphate by the addition of an isoprene unit from isopentenyl pyrophosphate. In Drosophila, geranylgeranyl pyrophosphate is synthesised...

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Geranyl pyrophosphate

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pathway that produces longer prenyl chains such as farnesyl pyrophosphate and geranylgeranyl pyrophosphate as well as many terpenes. It can be prepared in...

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Terpene

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proceeds via formation of geranyl pyrophosphate (GPP), farnesyl pyrophosphate (FPP), and geranylgeranyl pyrophosphate (GGPP). In both MVA and MEP pathways...

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Limonene

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ketone-containing carvone. In nature, limonene is formed from geranyl pyrophosphate, via cyclization of a neryl carbocation or its equivalent as shown....

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Farnesol

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animals. When geranyl pyrophosphate reacts with isopentenyl pyrophosphate, the result is the 15-carbon farnesyl pyrophosphate, which is an intermediate...

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Dimethylallyltranstransferase

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all the structural information available in the PDB for UniProt: P14324 (Human Farnesyl pyrophosphate synthaseC) at the PDBe-KB. Portal: Biology v t e...

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Natural rubber

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converts three monomers of isopentenyl pyrophosphate into farnesyl pyrophosphate. The farnesyl pyrophosphate can bind to rubber transferase to elongate...

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Dimethylallyl pyrophosphate

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Dimethylallyl pyrophosphate (DMAPP; or alternatively, dimethylallyl diphosphate (DMADP); also isoprenyl pyrophosphate) is an isoprenoid precursor. It...

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Squalene

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Archaea. Squalene is biosynthesised by coupling two molecules of farnesyl pyrophosphate. The condensation requires NADPH and the enzyme squalene synthase...

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Monoterpene

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isopentenyl pyrophosphate isomerase. Geranyl pyrophosphate is the precursor to monoterpenes (and hence monoterpenoids). Elimination of the pyrophosphate group...

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Terpenoid

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intermediates produced from geranyl pyrophosphate. Analogously hydrolysis of intermediates from farnesyl pyrophosphate gives sesquiterpenoids, and hydrolysis...

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Geosmin

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produced from the universal sesquiterpene precursor farnesyl pyrophosphate (also known as farnesyl diphosphate), in a two-step Mg2+-dependent reaction...

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Prenylation

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geranyl pyrophosphate (10 carbons), farnesyl pyrophosphate (15 carbons) and geranylgeranyl pyrophosphate (20 carbons). Two farnesyl pyrophosphate groups...

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Bisphosphonate

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bisphosphonate group mimics the structure of pyrophosphate, it can inhibit activation of enzymes that utilize pyrophosphate. The specificity of bisphosphonate-based...

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Isopentenyl pyrophosphate

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Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP) is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase...

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Sesquiterpene

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atmosphere. The reaction of geranyl pyrophosphate with isopentenyl pyrophosphate results in the 15-carbon farnesyl pyrophosphate (FPP), which is an intermediate...

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Lycopene

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dimethylallyl pyrophosphate. This is then condensed with three molecules of isopentenyl pyrophosphate (an isomer of dimethylallyl pyrophosphate), to give...

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Drimenol cyclase

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Drimenol cyclase (EC 3.1.7.7, farnesyl pyrophosphate:drimenol cyclase) is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphohydrolase...

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Farnesyltransferase

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JF, Casey PJ (1995). "Protein farnesyltransferase: kinetics of farnesyl pyrophosphate binding and product release". Biochemistry. 34 (20): 6857–62. doi:10...

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Zingiberene

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pathway from farnesyl pyrophosphate (FPP). FPP undergoes a rearrangement to give nerolidyl diphosphate. After the removal of pyrophosphate, the ring closes...

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Saponin

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Sesquiterpenoids (3) Artemisinin Bisabolol Cadinene Cadinol Cedrene Chanootin Farnesyl pyrophosphate Juniperol Longifolene Muurolene Nootkatin Diterpenoids (4) Sesterterpenoids...

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Alendronic acid

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is chemically related to inorganic pyrophosphate, the endogenous regulator of bone turnover. But while pyrophosphate inhibits both osteoclastic bone resorption...

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Triterpene

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is biosynthesized through the head-to-head condensation of two farnesyl pyrophosphate units. This coupling converts a pair of C15 components into a C30...

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Minodronic acid

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of osteoporosis. Its mechanism of action involves inhibition of farnesyl pyrophosphate synthase activity. Shridhar Hegde and Michelle Schmidt (2009). "To...

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Valencene

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inexpensively from Valencia oranges. Valencene is biosynthesized from farnesyl pyrophosphate (FPP) by the CVS enzyme. It is used as a precursor to nootkatone...

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Zoledronic acid

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Zoledronic acid, also known as zoledronate and sold under the brand name Zometa by Novartis among others, is a medication used to treat a number of bone...

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