Farnesyl pyrophosphate

Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is the precursor to all sesquiterpenes, which comprises thousands of compounds.^[1] These 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).

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	372-97-4 Y
3D model (JSmol)	Interactive image
ChemSpider	393270 N
MeSH	farnesyl+pyrophosphate
PubChem CID	445713
UNII	G8X8WT527W Y
CompTox Dashboard (EPA)	DTXSID701020624
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). N verify (what is YN ?) Infobox references

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]

Related compounds

• Farnesene
• Farnesol
• Geranyl pyrophosphate
• Geranylgeranyl pyrophosphate