1.0 2010-04-08 22:06:53 UTC 2019-11-26 03:00:50 UTC FDB005891 Parthenolide Parthenolide 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. Thus, parthenolide is considered to be an isoprenoid lipid molecule. Parthenolide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Parthenolide is a bitter tasting compound found in sweet bay, which makes parthenolide a potential biomarker for the consumption of this food product. Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named. It is found in highest concentration in the flowers and fruit . (-)-parthenolide Feverfew 125mg Parthenolide C15H20O3 248.3175 248.141244506 (1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one (-)-parthenolide 20554-84-1 C\C1=C/CC[C@@]2(C)O[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC1 InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1 KTEXNACQROZXEV-SLXBATTESA-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 Carbonyl compounds Dialkyl ethers Enoate esters Epoxides Gamma butyrolactones Germacrane sesquiterpenoids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Tetrahydrofurans Aliphatic heteropolycyclic compound Alpha,beta-unsaturated carboxylic ester Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl ether Enoate ester Ether Gamma butyrolactone Germacrane sesquiterpenoid Germacranolide Hydrocarbon derivative Lactone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxirane Sesquiterpenoid Tetrahydrofuran Germacrane sesquiterpenoids Germacrane sesquiterpenoids Germacrenes logp 3.03 ALOGPS logs -3.10 ALOGPS solubility 1.96e-01 g/l ALOGPS logp 3.07 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one ChemAxon average_mass 248.3175 ChemAxon mono_mass 248.141244506 ChemAxon smiles C\C1=C/CC[C@@]2(C)O[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC1 ChemAxon formula C15H20O3 ChemAxon inchi InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1 ChemAxon inchikey KTEXNACQROZXEV-SLXBATTESA-N ChemAxon polar_surface_area 38.83 ChemAxon refractivity 68.55 ChemAxon polarizability 26.8 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 6280 Specdb::MsMs 246549 Specdb::MsMs 246550 Specdb::MsMs 246551 Specdb::MsMs 266493 Specdb::MsMs 266494 Specdb::MsMs 266495 Sweet bay Type 1 specific Laurus nobilis 85223 bitter 5-hydroxytryptamine inhibitor 9 Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists. 5-lipoxygenase inhibitor 10 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. allelopathic 42 allergenic 43 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. anti aggregant 94 anti arthritic 131 Any substance introduced into a living organism with therapeutic or diagnostic purpose. anti bacterial 145 A substance that kills or slows the growth of bacteria. anti cancer 159 A substance that inhibits or prevents the proliferation of neoplasms. anti inflammatory 370 A substance that reduces or suppresses inflammation. anti migraine 437 Any substance introduced into a living organism with therapeutic or diagnostic purpose. anti neuralgic 469 Any substance introduced into a living organism with therapeutic or diagnostic purpose. anti prostaglandin 550 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. anti secretory 601 anti septic 603 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. anti spasmodic 619 Any substance introduced into a living organism with therapeutic or diagnostic purpose. antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. candidicide 756 cyclooxygenase inhibitor 849 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. cyclooxygenase-2 inhibitor 841 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. dermatitigenic 875 fungicide 940 A substance used to destroy fungal pests. Gram(+)icide 962 A substance that kills or slows the growth of bacteria. hypercalcuric 1002 pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. phospholipase inhibitor 1217 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. prostaglandin-synthetase inhibitor 1259 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.