1.0 2010-04-08 22:10:23 UTC 2019-11-26 03:07:41 UTC FDB012837 Rotenone Widely distrib. in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean) Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the roots and stems of several plants such as the jicama vine plant. In mammals, including humans, it is linked to the development of Parkinson's disease. Rotenone is found in jicama and pulses. (-)-cis-Rotenone (-)-Rotenone [2R-(2a,6Aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one [2R-(2alpha,6Aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one [2R-(2α,6aalpha,12aalpha)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one 1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 9CI 5'beta-rotenone Barbasco Canex Dactinol Derrin Derris Derris, JMAF Dri-kil Nicouline Noxfire Noxfish Paraderil Tubatoxin Tubotoxin C23H22O6 394.4172 394.141638436 (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one 83-79-4 [H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1 JUVIOZPCNVVQFO-HBGVWJBISA-N belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. Rotenones Organic compounds Phenylpropanoids and polyketides Isoflavonoids Rotenoids Aromatic heteropolycyclic compounds 8-prenylated isoflavanones Alkyl aryl ethers Anisoles Aryl alkyl ketones Chromones Coumarans Hydrocarbon derivatives Organic oxides Oxacyclic compounds 1-benzopyran 8-prenylated isoflavanone Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzopyran Chromane Chromone Coumaran Ether Hydrocarbon derivative Isoflavan Isoflavanone Ketone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Rotenone or derivatives Pesticides Rotenoid flavonoids Rotenoid flavonoids organic heteropentacyclic compound rotenones rotenones logp 2.30 ALOGPS logs -4.49 ALOGPS solubility 1.29e-02 g/l ALOGPS melting_point Mp 163° logp 3.32 ChemAxon pka_strongest_acidic 11.8 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one ChemAxon average_mass 394.4172 ChemAxon mono_mass 394.141638436 ChemAxon smiles [H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C ChemAxon formula C23H22O6 ChemAxon inchi InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1 ChemAxon inchikey JUVIOZPCNVVQFO-HBGVWJBISA-N ChemAxon polar_surface_area 63.22 ChemAxon refractivity 105.71 ChemAxon polarizability 42.07 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 6 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 46 Specdb::CMs 18392 Specdb::CMs 132005 Specdb::CMs 139739 Specdb::NmrOneD 2665 Specdb::MsMs 254067 Specdb::MsMs 254068 Specdb::MsMs 254069 Specdb::MsMs 274008 Specdb::MsMs 274009 Specdb::MsMs 274010 Specdb::MsMs 445400 Specdb::MsMs 445401 Specdb::MsMs 445402 Specdb::MsMs 447441 Specdb::MsMs 447442 Specdb::MsMs 447443 Specdb::MsMs 447444 Specdb::MsMs 447445 Specdb::MsMs 447446 Specdb::MsMs 2235822 Specdb::MsMs 2236305 Specdb::MsMs 2237058 Specdb::MsMs 2237572 Specdb::MsMs 2237880 Specdb::MsMs 2239680 Specdb::MsMs 2240038 Specdb::MsMs 2241692 Specdb::MsMs 2242130 Specdb::MsMs 2242577 HMDB34436 28201 #<Reference:0x000055ce327b1c80> #<Reference:0x000055ce327b1ac8> #<Reference:0x000055ce327b18e8> Jicama Type 1 specific Pachyrhizus erosus 109171 Pulses Unknown generic