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Pathway Description
Cannabinoid Biosynthesis
Cannabis sativa
Metabolic Pathway
Hexanoate is first catalyzed to make hexanoyl-CoA with the enzyme hexanoyl CoA synthase in the cytosol and within the membrane of the cell. Hexanoyl-CoA branches paths to olivetol biosynthesis which creates the byproducts of this pathway. The other pathway is catalyzed by olivetol synthase to make 3,5-dioxodecanoyl-CoA which is catalyzed to make 3,5,7-trioxododecanoyl-CoA. This is similar to the olivetol biosynthesis pathway, however here 3,5,7-trioxododecanoyl-CoA is catalyzed by olivetolic acid cyclase to make olivetolate. This takes place in the cytoplasm. Olivetolate along with geranyl diphosphate is catalyzed by olivetolate geranyltransferase to make cannabigerolate or cannabigerolic acid.
This compound branches into three separate pathways each catalyzed by a different enzymes. One pathway is catalyzed by Δ9-tetrahydrocannabinolate synthase along with oxygen to make Δ9-tetrahydrocannabinolate. This compound spontaneously reacts with hydrogen to synthesize the drug Δ9-tetrahydrocannabinol (THC). The second pathway is catalyzed by cannabidiolate synthase and oxygen to make cannabidiolate or cannabidiolic acid. Cannabidiolate spontaneously reacts with hydrogen to synthesize the drug cannabidiol (CBD). The final pathway is catalyzed by cannabichromenate synthase along with an unknown oxidized electron carrier to make cannabichromenate or cannabichromenic acid. This, like the others, spontaneously reacts with hydrogen to synthesize the drug cannabichromene (CBC).
References
Cannabinoid Biosynthesis References
Baker PB, Taylor BJ, Gough TA: The tetrahydrocannabinol and tetrahydrocannabinolic acid content of cannabis products. J Pharm Pharmacol. 1981 Jun;33(6):369-72. doi: 10.1111/j.2042-7158.1981.tb13806.x.
Pubmed: 6115009
Bosy TZ, Cole KA: Consumption and quantitation of delta9-tetrahydrocannabinol in commercially available hemp seed oil products. J Anal Toxicol. 2000 Oct;24(7):562-6. doi: 10.1093/jat/24.7.562.
Pubmed: 11043660
Fellermeier M, Eisenreich W, Bacher A, Zenk MH: Biosynthesis of cannabinoids. Incorporation experiments with (13)C-labeled glucoses. Eur J Biochem. 2001 Mar;268(6):1596-604. doi: 10.1046/j.1432-1033.2001.02030.x.
Pubmed: 11248677
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
Morimoto S, Komatsu K, Taura F, Shoyama Y: Purification and characterization of cannabichromenic acid synthase from Cannabis sativa. Phytochemistry. 1998 Nov;49(6):1525-9. doi: 10.1016/s0031-9422(98)00278-7.
Pubmed: 9862135
Raharjo TJ, Chang WT, Verberne MC, Peltenburg-Looman AM, Linthorst HJ, Verpoorte R: Cloning and over-expression of a cDNA encoding a polyketide synthase from Cannabis sativa. Plant Physiol Biochem. 2004 Apr;42(4):291-7. doi: 10.1016/j.plaphy.2004.02.011.
Pubmed: 15120113
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