Farnesyl pyrophosphate
Identifiers
CAS number	13058-04-3
PubChem	706
MeSH	farnesyl+pyrophosphate
Properties
Molecular formula	C15H28O7P2
Molar mass	382.326
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Farnesyl pyrophosphate (FPP) is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids.

It is the immediate precursor of squalene (via the enzyme squalene synthase), dehydrodolichol diphosphate (a precursor of dolichol), and geranylgeranyl pyrophoshate (GGPP).

[edit] Biosynthesis

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

• Dimethylallyl pyrophosphate reacts with 3-isopentenyl pyrophosphate to form geranyl pyrophosphate:

• Geranyl pyrophosphate itself reacts with 3-isopentenyl pyrophosphate to form farnesyl pyrophosphate

[edit] Regulation

The above reactions are inhibited by bisphosphonates (used for osteoporosis).

[edit] Related compounds

• Farnesene
• Farnesol
• Geranyl pyrophosphate
• Geranylgeranyl pyrophosphate

v • d • e Cholesterol and steroid metabolic intermediates Mevalonate pathway to HMG-CoA Acetyl-CoA · Acetoacetyl-CoA · HMG-CoA Ketone bodies Acetone · Acetoacetic acid · beta-Hydroxybutyric acid to DMAPP Mevalonic acid · Phosphomevalonic acid · 5-Diphosphomevalonic acid · Isopentenyl pyrophosphate · Dimethylallyl pyrophosphate Geranyl- Geranyl pyrophosphate · Geranylgeranyl pyrophosphate Carotenoid Prephytoene diphosphate · Phytoene Non-mevalonate pathway DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP To Cholesterol Farnesyl pyrophosphate · Squalene · 2,3-Oxidosqualene · Lanosterol Lanosterol · Lathosterol · 7-Dehydrocholesterol · Cholesterol Lanosterol · Zymosterol · 7-Dehydrodesmosterol · Desmosterol · Cholesterol Steroid Corticosteroids (C21 pregnane) Mineralocorticoids Pregnenolone · Progesterone · 11-Deoxycorticosterone · Corticosterone · Aldosterone Glucocorticoids Pregnenolone · 17-Hydroxypregnenolone · 17-Hydroxyprogesterone · 11-Deoxycortisol · Cortisol Cortisol · Cortisone Sex steroids Androgens (C19 andrane) DHEA · Androstenedione/5-Androstenediol · Testosterone · Dihydrotestosterone DHEA sulfate · Epitestosterone Estrogens (C18 estrane) Estrone · Estradiol · Estriol Nonhuman Phytosterols Stigmasterol · Brassicasterol Ergosterols Ergosterol · Ergocalciferol see also enzymes, disorders Major families of biochemicals Saccharides/Carbohydrates/Glycosides · Amino acids/Peptides/Proteins/Glycoproteins · Lipids/Terpenes/Steroids/Carotenoids · Alkaloids/Nucleobases/Nucleic acids · Cofactors/Phenylpropanoids/Polyketides/Tetrapyrroles

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