1.0 2010-04-08 22:11:57 UTC 2019-11-26 03:11:56 UTC FDB015620 Eucannabinolide Eucannabinolide belongs to germacranolides and derivatives class of compounds. Those are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Eucannabinolide is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eucannabinolide can be found in roman camomile, which makes eucannabinolide a potential biomarker for the consumption of this food product. Eucannabinolide Eupaformosanin Hiyodorilactone A Hydroxychromolaenide Schkuhrin I C22H28O8 420.4529 420.178417872 9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate 9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate 38458-58-1 CC(=O)OC1C\C=C(C)\CC(OC(=O)C(\CO)=C\CO)C2C(OC(=O)C2=C)\C=C1/C InChI=1S/C22H28O8/c1-12-5-6-17(28-15(4)25)13(2)10-19-20(14(3)21(26)29-19)18(9-12)30-22(27)16(11-24)7-8-23/h5,7,10,17-20,23-24H,3,6,8-9,11H2,1-2,4H3/b12-5+,13-10+,16-7+ XYPJAWWDSQFSQA-VISQRNLASA-N belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Germacranolides and derivatives Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aliphatic heteropolycyclic compounds Beta hydroxy acids and derivatives Carbonyl compounds Enoate esters Fatty acid esters Gamma butyrolactones Germacrane sesquiterpenoids Hydrocarbon derivatives Organic oxides Oxacyclic compounds Primary alcohols Tetrahydrofurans Tricarboxylic acids and derivatives Alcohol Aliphatic heteropolycyclic compound Alpha,beta-unsaturated carboxylic ester Beta-hydroxy acid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Enoate ester Fatty acid ester Fatty acyl Gamma butyrolactone Germacrane sesquiterpenoid Germacranolide Hydrocarbon derivative Hydroxy acid Lactone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Primary alcohol Sesquiterpenoid Tetrahydrofuran Tricarboxylic acid or derivatives logp 1.59 ALOGPS logs -3.76 ALOGPS solubility 7.24e-02 g/l ALOGPS logp 1.33 ChemAxon pka_strongest_acidic 6.18 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac 9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate ChemAxon average_mass 420.4529 ChemAxon mono_mass 420.178417872 ChemAxon smiles CC(=O)OC1C\C=C(C)\CC(OC(=O)C(\CO)=C\CO)C2C(OC(=O)C2=C)\C=C1/C ChemAxon formula C22H28O8 ChemAxon inchi InChI=1S/C22H28O8/c1-12-5-6-17(28-15(4)25)13(2)10-19-20(14(3)21(26)29-19)18(9-12)30-22(27)16(11-24)7-8-23/h5,7,10,17-20,23-24H,3,6,8-9,11H2,1-2,4H3/b12-5+,13-10+,16-7+ ChemAxon inchikey XYPJAWWDSQFSQA-VISQRNLASA-N ChemAxon polar_surface_area 119.36 ChemAxon refractivity 109.56 ChemAxon polarizability 43.3 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 87666 Specdb::MsMs 87667 Specdb::MsMs 87668 Specdb::MsMs 150225 Specdb::MsMs 150226 Specdb::MsMs 150227 Specdb::MsMs 3605827 Specdb::MsMs 3605828 Specdb::MsMs 3605829 Specdb::MsMs 3605830 Specdb::MsMs 3605831 Specdb::MsMs 3605832 Roman camomile Type 1 specific Chamaemelum nobile 99037