Terpene

Geranyl pyrophosphate
Identifiers
CAS Number	763-10-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17211 ;
ChEMBL	ChEMBL41342 ;
ChemSpider	393471 ;
DrugBank	DB02552 ;
IUPHAR/BPS	3051;
MeSH	Geranyl+pyrophosphate
PubChem CID	445995;
	InChI InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+ Key: GVVPGTZRZFNKDS-JXMROGBWSA-N ; InChI=1/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+ Key: GVVPGTZRZFNKDS-JXMROGBWBE;
	SMILES O=P(O)(O)OP(=O)(OC/C=C(/CC\C=C(/C)C)C)O;
Properties
Chemical formula	C10H17O7P2
Molar mass	311,19
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of farnesyl pyrophosphate and geranylgeranyl pyrophosphate.^[1] These species are respectively precursors to sesquiterpenes and diterpenes.^[2]

Isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) are condensed by geranyl pyrophosphate synthase (dimethylallyltranstransferase) to produce geranyl pyrophosphate (GPP) and pyrophosphate. The carbon skeletons of DMAPP and IPP have been colored to indicate their location in GPP.

Related compounds[edit]

^ Davis, Edward M.; Croteau, Rodney (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.CS1 maint: uses authors parameter (link)
^ Bohlmann, Jorg; Gershenzon, Jonathan (2009). "Old Substrates for New Enzymes of Terpenoid Biosynthesis". Proceedings of the National Academy of Sciences of the United States of America. 106 (26): 10402–10403. Bibcode:2009PNAS..10610402B. doi:10.1073/pnas.0905226106. PMC 2705528. PMID 19553206.CS1 maint: uses authors parameter (link)

Identifiers


CAS Number	763-10-0^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17211^Y
ChEMBL	ChEMBL41342^Y
ChemSpider	393471^Y
DrugBank	DB02552^Y
IUPHAR/BPS	3051
MeSH	Geranyl+pyrophosphate
PubChem CID	445995
InChI InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+^Y Key: GVVPGTZRZFNKDS-JXMROGBWSA-N^Y InChI=1/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+ Key: GVVPGTZRZFNKDS-JXMROGBWBE
SMILES O=P(O)(O)OP(=O)(OC/C=C(/CC\C=C(/C)C)C)O
Properties
Chemical formula	C₁₀H₁₇O₇P₂
Molar mass	311,19
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