1.0 2010-04-08 22:10:09 UTC 2025-11-18 23:36:30 UTC FDB012420 (-)-cis-Rotenolone Isolated from Pachyrrhizus erosus (yam bean). (-)-cis-Rotenolone is found in jicama and pulses. (-)-cis-12a-Hydroxyrotenone [1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aR,12aR)- 1,2,12,12a-Tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-(2R,6ar,12ar)-[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-one 12-Hydroxyrotenone 12a-Hydroxyrotenone 12alpha-Hydroxyrotenone 6a-beta,12a-beta-Rotenolone 6ab,12ab-Rotenolone Rotenalone Rotenolon I Rotenolone Rotenolone I Rotenolone; (-)-cis-form C23H22O7 410.4166 410.136553058 (1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-12-one rotenolone 509-96-6 [H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1 JFVKWCYZKMUTLH-AYPBNUJASA-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 Tertiary alcohols 1-benzopyran 8-prenylated isoflavanone Alcohol 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 Tertiary alcohol organic molecular entity rotenones logp 2.40 ALOGPS logs -3.87 ALOGPS solubility 5.58e-02 g/l ALOGPS melting_point Mp 91-92° (88°) logp 2.73 ChemAxon pka_strongest_acidic 11.08 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-12-one ChemAxon average_mass 410.4166 ChemAxon mono_mass 410.136553058 ChemAxon smiles [H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C ChemAxon formula C23H22O7 ChemAxon inchi InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1 ChemAxon inchikey JFVKWCYZKMUTLH-AYPBNUJASA-N ChemAxon polar_surface_area 83.45 ChemAxon refractivity 106.96 ChemAxon polarizability 42.8 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 7 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 15866 Specdb::CMs 43734 Specdb::CMs 159170 Specdb::MsMs 68592 Specdb::MsMs 68593 Specdb::MsMs 68594 Specdb::MsMs 126660 Specdb::MsMs 126661 Specdb::MsMs 126662 Specdb::MsMs 2327274 Specdb::MsMs 2327275 Specdb::MsMs 2327276 Specdb::MsMs 2612122 Specdb::MsMs 2612123 Specdb::MsMs 2612124 HMDB34145 #<Reference:0x000055ce32110e58> Jicama Type 1 specific Pachyrhizus erosus 109171 Pulses Unknown generic