1.0 2020-03-18 23:25:18 UTC 2020-12-07 19:07:07 UTC CDB000114 beta-Humulene Beta-humulene belongs to the class of organic compounds known as sesquiterpenoids. These 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 cytoplasm (PMID:23746261). 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. Beta-humulene is possibly neutral. Beta-humulene is found in hops (Humulus lupulus) a member of the Cannabaceae family and in Cannabis plants (PMID: 6991645). It is also detected in allspice and guava fruit, celery seed, lemon oil and spearmint leaf ( http://www.thegoodscentscompany.com/data/rw1539551.html#tooccur ). b-Humulene Β-humulene (e,e)-1,4,4-Trimethyl-8-methylene-1,5-cycloundecadiene 1,4,4-Trimethyl-8-methylene-(e,e)-1,5-cycloundecadiene 1,4,4-Trimethyl-8-methylene-1,5-cycloundecadiene C15H24 204.35 204.1878 (1Z,5Z)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene (1Z,5Z)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene 116-04-1 C\C1=C\CC(C)(C)\C=C/CC(=C)CCC1 InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6,10-11H,1,5,7-9,12H2,2-4H3/b11-6-,14-10- HAVYZKHVTLAPDZ-PRUKLFJYSA-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 homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Humulane sesquiterpenoid Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon melting_point < 25 °C logp 5.97 ALOGPS logs -4.93 ALOGPS logp 4.94 ChemAxon iupac (1Z,5Z)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles C\C1=C\CC(C)(C)\C=C/CC(=C)CCC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6,10-11H,1,5,7-9,12H2,2-4H3/b11-6-,14-10- ChemAxon inchikey HAVYZKHVTLAPDZ-PRUKLFJYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 70.48 ChemAxon polarizability 26.04 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 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB017456 20120040 21159064 C00012455 49312 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261