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Farnesyl pyrophosphate

Chemical compound From Wikipedia, the free encyclopedia

Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is the precursor to all sesquiterpenes, which comprises thousands of compounds.[1] These[clarification needed] include all sesquiterpenes as well as sterols and carotenoids.[2] 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).

Quick facts Names, Identifiers ...
Farnesyl pyrophosphate
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl trihydrogen diphosphate
Identifiers
3D model (JSmol)
ChemSpider
MeSH farnesyl+pyrophosphate
UNII
  • 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
  • CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)C
Properties
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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Biosynthesis

Farnesyl pyrophosphate synthase (a prenyl transferase)[3] catalyzes sequential condensation reactions of dimethylallyl pyrophosphate with 2 units of 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate:

Pharmacology

The above reactions are inhibited by bisphosphonates (used for osteoporosis).[4] Farnesyl pyrophosphate is a selective agonist of TRPV3.[5]

References

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