Compound: rotenone
SMILES: O=C1c2c(O[C@H]3[C@@H]1c4c(OC3)cc(OC)c(c4)OC)c5c(O[C@H](C5)C(=C)C)cc2
InChIKey: JUVIOZPCNVVQFO-HBGVWJBISA-N
Synonyms: rotenone, 83-79-4, Dactinol, Paraderil, Tubatoxin, (-)-Rotenone, Derrin, Derris, Nicouline, (-)-cis-Rotenone, Deril, Liquid Derris, Cube-Pulver, Dri-Kil, Rotocide, Noxfire, Ronone, Rotenon, Canex, Rotefive, Rotefour, Rotessenol, Tubotoxin, Extrax, Haiari, Mexide, Rotenox, Cubor, Chem-Mite, Cenol garden dust, Curex flea duster, Synpren, Gerane, Ro-Ko, Derris (insecticide), Pb-nox, Rotenox 5EC, 5'-beta-Rotenone, Nekoe, Green Cross Warble Powder, Foliafume E.C., Rotenona, ENT 133, Rotacide E.C., NCI-C55210, CUBE, DTXSID6021248, NSC26258, 03L9OT429T, NSC-26258, 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, DTXCID901248, (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-alpha-isopropenyl-8,9-dimethoxy-, (1S,6R,13S)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one, CHEBI:28201, (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)-, (2R-(2alpha,6aalpha,12aalpha))-, (12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano[3,4-b]furano [2,3-h]chroman-6-one, (2R,6aS,12aS)-1,2,6,6a,12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno(3,4-b)furo(2,3-h)chromen-6-one, (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)-, (2R,6aS,12aS)-, [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,6aS,12aS)-1,2,6,6a,12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno[3,4-b]furo[2,3-h]chromen-6-one, [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)-, (2R,6aS,12aS)-, (12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano(3,4-b)furano (2,3-h)chroman-6-one, (1S,6R,13S)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo(11.8.0.03,11.04,8.014,19)henicosa-3(11),4(8),9,14,16,18-hexaen-12-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, [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)-, [2R-(2alpha,6aalpha,12aalpha)]-, TUBOTOXINE, RefChem:179947, (1S,13S)-16,17-dimethoxy-2,7,20-trioxapentacyclo(11.8.0.03,11.04,8.014,19)henicosa-3(11),4(8),9,14,16,18-hexaen-12-one, 201-501-9, Prentox, Caswell No. 725, Rotenone, commercial, CCRIS 895, HSDB 1762, MFCD09025614, EPA Pesticide Chemical Code 071003, AI3-00133, Rotenone, dehydro, Derris resins, MLS000738056, CHEMBL429023, (2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-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)benzopyran-6(6aH)-one, 1,2,12,12aalpha-Tetrahydro-2a-isopropenyl-8,9-dimethoxy(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, NCGC00017358-05, (2R,6aS,12aS)-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrofuro[2',3':7,8][1]benzopyrano[2,3-c][1]benzopyran-6(6aH)-one, Rotenona [Spanish], Rotenone [BSI:ISO], Protax, 5'.beta.-Rotenone, CAS-83-79-4, (2R,6aS,12aS)-1,2,6,6a,12,12a- hexahydro-2-isopropenyl-8,9- dimethoxychromeno[3,4-b] furo(2,3-h)chromen-6-one, (2R,6aS,12aS)-2-isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one, SR-01000076110, EINECS 201-501-9, NSC 26258, Rotenoid, UNII-03L9OT429T, Nicouline;, Paraderil;, WLN: T G5 D6 B666 CV HO MO POT&TT&J IY1&U1 SO1 TO1, Dactinol;, Noxfish;, Derrin;, Derris;, 5''beta-rotenone, 5'b-Rotenone, Dri-kil;, Rotocide E.C., (1)Benzopyrano[3,3-h](1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-.alpha.-iospropenyl-8,9-dimethoxy-, [1]Benzopyrano[3,3-h][1]benzopyran-6(6a.alpha.H)-one, 1,2,12,12a.alpha.-tetrahydro-2.alpha.-isopropenyl-8,9-dimethoxy-, [1]Benzopyrano[3,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, [2R-(2.alpha.,6a.alpha.,12a.alpha.)]-, Derris, JMAF, Prestwick_542, Rotenone (7CI), Rotenone (Standard), Rotenone, >=95%, Spectrum_000065, ROTENONE [HSDB], ROTENONE [ISO], ROTENONE [MI], Spectrum2_000457, Spectrum3_000158, Spectrum4_001638, Spectrum5_000455, GlyTouCan:G26488SP, ROTENONE [MART.], Lopac0_001112, SCHEMBL42253, BSPBio_001896, KBioGR_002075, KBioSS_000465, SPECTRUM200013, (2R-(6aalpha,12aalpha)-1,2-Dihydro-2-isopropenyl-8,9-dimethoxychromano(3,4-b)furo(2,3-h)chroman-6-on, DivK1c_000947, ROTENONE [GREEN BOOK], SPBio_000534, orb1304789, SCHEMBL29388856, HMS502P09, HY-B1756R, KBio1_000947, KBio2_000465, KBio2_003033, KBio2_005601, KBio3_001116, inhibits NADH2 oxidation to NAD, NSC8505, NINDS_000947, GLXC-07705, HMS3263O06, HMS6018H03, G26488SP, HY-B1756, MSK20286, NSC-8505, TNP00301, Tox21_110819, Tox21_201904, Tox21_300695, Tox21_501112, BDBM50135527, CCG-39886, HB5398, LMPK12060007, SBB006465, AKOS004910398, Tox21_110819_1, CS-6067, DB11457, EBC-457082, FR65511, LP01112, SDCCGMLS-0066415.P001, SDCCGSBI-0051081.P003, IDI1_000947, Rotenone 100 microg/mL in Acetonitrile, NCGC00017358-01, NCGC00017358-02, NCGC00017358-03, NCGC00017358-04, NCGC00017358-06, NCGC00017358-07, NCGC00017358-08, NCGC00017358-09, NCGC00017358-10, NCGC00017358-11, NCGC00017358-14, NCGC00017358-15, NCGC00017358-22, NCGC00094382-01, NCGC00094382-02, NCGC00094382-03, NCGC00094382-04, NCGC00094382-05, NCGC00254603-01, NCGC00259453-01, NCGC00261797-01, AC-31290, AS-10183, DA-77540, NCI60_002093, SMR000393729, ST057261, SY102181, EU-0101112, NS00007117, R0090, Rotenone, PESTANAL(R), analytical standard, C07593, R 8875, Q412388, SR-01000076110-2, SR-01000076110-5, SR-01000076110-6, BRD-K08316444-001-01-9, BRD-K08316444-001-05-0, (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)-6-isopropenyl-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one, (2R,6AS,12AS)-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-(6aalpha,12aalpha)-1,2-Dihydro-2-isopropenyl-8,9-dimethoxychromano(3,4-b)furo(2,3-h)chroman-6-one, [1]Benzopyrano[3,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-.alpha.-isopropenyl-8,9-dimethoxy-, [1]Benzopyrano[3,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-isopropenyl-8,9-dimethoxy-, [1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aalphaH)-one, 1,2,12,12aalpha-tetrahydro-2alpha-isopropenyl-8,9-dimethoxy- (8CI), [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)-, (2R,6aS,12aS)- (9CI), 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, Tubatoxin 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
Theoretical properties:
molecular_formula: C23H22O6
molecular_weight: 394.4 g/mol
exact_mass: 394.14163842 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 3
heavy_atom_count: 29
topological_polar_surface_area: 63.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Orthorhombic, six-sided plates from trichloroethylene
color: Orthorhombic, six-sided plates from trichloroethylene
odor: Odorless
boiling_point: 410 to 428 °F at 0.5 mmHg (NTP, 1992)
melting_point: 329 to 331 °F (NTP, 1992)
density: 1.27 at 68 °F (NTP, 1992) - Denser than water; will sink
solubility: less than 1 mg/mL at 68 °F (NTP, 1992)
vapor_pressure: less than 0.0075 mmHg at 68 °F (NTP, 1992)
Descriptions:
pubchem: Rotenone is a member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica). It has a role as a piscicide, a phytogenic insecticide, a metabolite, a toxin, an antineoplastic agent and a mitochondrial NADH:ubiquinone reductase inhibitor. It is an organic heteropentacyclic compound and a member of rotenones.
chebi: A member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-<em>b</em>]furo[2,3-<em>h</em>]chromen-6(6a<em>H</em>)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2<i>R</i>,6a<i>S</i>,12a<i>S</i>-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of <em>Derris elliptica</em>).
chembl: ROTENONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Rotenone is an organic compound that has been described as "by far the most important rotenoid." It is an odorless, colorless, crystalline isoflavone. It occurs naturally in the seeds and stems of several plants, such as the jicama vine, and in the roots of several other members of the Fabaceae. It was the first-described member of the family of chemical compounds known as rotenoids. Rotenone is approved for use as a piscicide to remove alien fish species, see Uses. It has also been used as a broad-spectrum insecticide, but its use as an insecticide has been banned in many countries.