1.0 2020-03-19 00:25:14 UTC 2020-11-18 16:34:56 UTC CDB000220 4a-Methyl-1-methylidene-7-(propan-2-ylidene)-decahydronaphthalene γ-Selinene belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. γ-Selinene is a woody tasting compound. It can found in the higher yields within a few different foods, such as gingers, limes, and mandarin orange (clementine, tangerine). γ-Selinene has also been detected, but not quantified, in a few different foods, such as alcoholic beverages, fats and oils, and wild celeries. The selinenes have been identified in a variety of plant sources, including Cannabis sativa (PMID: 26657499). There are four known selinene isomers, namely α-, β-, γ-, and δ-selinene. α-Selinene and β-selinene are the most common and are two of the principal components of the oil from celery seeds. γ-Selinene and δ-selinene are less common. C15H24 204.36 204.1878 (4aR,8aR)-4a-methyl-1-methylidene-7-(propan-2-ylidene)-decahydronaphthalene (4aR,8aR)-4a-methyl-1-methylidene-7-(propan-2-ylidene)-hexahydro-2H-naphthalene 515-17-3 CC(C)=C1CC[C@@]2(C)CCCC(=C)[C@H]2C1 InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h14H,3,5-10H2,1-2,4H3/t14-,15-/m1/s1 RMZHSBMIZBMVMN-HUUCEWRRSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 5.27 ALOGPS logs -4.09 ALOGPS logp 4.48 ChemAxon iupac (4aR,8aR)-4a-methyl-1-methylidene-7-(propan-2-ylidene)-decahydronaphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=C1CC[C@@]2(C)CCCC(=C)[C@H]2C1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h14H,3,5-10H2,1-2,4H3/t14-,15-/m1/s1 ChemAxon inchikey RMZHSBMIZBMVMN-HUUCEWRRSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.19 ChemAxon polarizability 25.83 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 162920675 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499