Loading Pathway...
Error: Pathway image not found.
Hide
Pathway Description
Olivetol Biosynthesis MetaCyc
Cannabis sativa
Metabolic Pathway
Olivetol is a compound involved in the biosynthesis of tetrahydrocannabinol (THC). The pathway starts with Hexanoyl-CoA and adds 2 hydrogen ions and 2 malonyl-CoA which is catalyzed by the enzyme 3,5,7-trioxododecanoyl-CoA synthase or olivetol synthase to produce 3,5-dioxodecanoyl-CoA as well as 2 coenzyme A and 2 carbon dioxide as a byproduct. The 3,5-dioxodecanoyl-CoA then is catalyzed in two reactions, one making triketide pyrone by way of the enzyme triketide pyrone synthase, and the other making 3,5,7-trioxododecanoyl-CoA with the enzyme olivetol synthase along with a hydrogen ion and malonyl-CoA, 3,5,7-trioxododecanoyl-CoA then is also catalyzed in two reactions. With the ensyme olivetol synthase in one reaction it makes olivetol.. In the other reaction with the same enzyme it makes tetraketide pyrone.
References
Olivetol Biosynthesis MetaCyc References
Fellermeier M, Zenk MH: Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol. FEBS Lett. 1998 May 8;427(2):283-5. doi: 10.1016/s0014-5793(98)00450-5.
Pubmed: 9607329
Flores-Sanchez IJ, Verpoorte R: PKS activities and biosynthesis of cannabinoids and flavonoids in Cannabis sativa L. plants. Plant Cell Physiol. 2008 Dec;49(12):1767-82. doi: 10.1093/pcp/pcn150. Epub 2008 Oct 14.
Pubmed: 18854334
Gagne SJ, Stout JM, Liu E, Boubakir Z, Clark SM, Page JE: Identification of olivetolic acid cyclase from Cannabis sativa reveals a unique catalytic route to plant polyketides. Proc Natl Acad Sci U S A. 2012 Jul 31;109(31):12811-6. doi: 10.1073/pnas.1200330109. Epub 2012 Jul 16.
Pubmed: 22802619
Highlighted elements will appear in red.
Highlight Compounds
Highlight Proteins
Enter relative concentration values (without units). Elements will be highlighted in a color gradient where red = lowest concentration and green = highest concentration. For the best results, view the pathway in Black and White.
Visualize Compound Data
Visualize Protein Data
Settings