Geranylgeranyl pyrophosphate

Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids.^[1] It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls.

Geranylgeranyl pyrophosphate

Names
Preferred IUPAC name (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl trihydrogen diphosphate
Other names geranylgeranyl diphosphate trans-geranylgeranyl diphosphate
Identifiers
CAS Number	6699-20-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48861 Y
ChemSpider	394418 Y
IUPHAR/BPS	3052
MeSH	geranylgeranyl+pyrophosphate
PubChem CID	447277
UNII	N21T0D88LX Y
CompTox Dashboard (EPA)	DTXSID90863929
InChI InChI=1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b18-11+,19-13+,20-15+ Y Key: OINNEUNVOZHBOX-QIRCYJPOSA-N Y InChI=1/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b18-11+,19-13+,20-15+ Key: OINNEUNVOZHBOX-QIRCYJPOBR
SMILES O=P(O)(O)OP(=O)(O)OC/C=C(/CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C)C
Properties
Chemical formula	C20H36O7P2
Molar mass	450.449 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

It is also a precursor to geranylgeranylated proteins, which is its primary use in human cells.^[2]

It is formed from farnesyl pyrophosphate by the addition of an isoprene unit from isopentenyl pyrophosphate.

In Drosophila, geranylgeranyl pyrophosphate is synthesised by HMG-CoA encoded by the Columbus gene. Geranylgeranyl pyrophosphate is utilised as a chemoattractant for migrating germ cells that have traversed the midgut epithelia. The attractant signal is produced at the gonadal precursors, directing the germ cells to these sites, where they will differentiate into eggs and spermatozoa (sperm).

Related compounds

• Farnesyl pyrophosphate
• Geranylgeraniol
• Geranyl pyrophosphate