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Rotenone

PubChem CID: 6758

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Compound Synonyms rotenone, 83-79-4, Dactinol, Paraderil, Barbasco, Tubatoxin, (-)-Rotenone, Derris, (-)-cis-Rotenone, Derrin, Nicouline, Rotocide, Noxfire, Ronone, Rotenon, Rotenox, Canex, Deril, Liquid Derris, Cube-Pulver, Dri-Kil, Rotessenol, Prentox, Rotefive, Rotefour, Tubotoxin, Cubor, Extrax, Haiari, Mexide, Chem-Mite, Pb-nox, Cenol garden dust, Curex flea duster, Gerane, Ro-Ko, Synpren, Derris (insecticide), Caswell No. 725, Rotenox 5EC, Foliafume E.C., 5'-beta-Rotenone, Green Cross Warble Powder, CCRIS 895, Rotenone [BSI:ISO], Rotenone, dehydro, HSDB 1762, Rotacide E.C., ENT 133, Rotenone, commercial, EPA Pesticide Chemical Code 071003, NCI-C55210, AI3-00133, NSC26258, EINECS 201-501-9, NSC 26258, Derris, JMAF, UNII-03L9OT429T, DTXSID6021248, CHEBI:28201, 03L9OT429T, ROTENONE [HSDB], C23H22O6, ROTENONE [ISO], ROTENONE [MI], NSC-26258, ROTENONE [MART.], (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, 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, Rotenona, ROTENONE [GREEN BOOK], Derris resins, MLS000738056, CHEMBL429023, 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-, (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)-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, 5'beta-Rotenone, Green cross warble, CUBE, (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))-, (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-(6aalpha,12aalpha)-1,2-Dihydro-2-isopropenyl-8,9-dimethoxychromano(3,4-b)furo(2,3-h)chroman-6-on, [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, NCGC00017358-05, Rotacide, Nekoe, ROTENONE (MART.), (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,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,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)-, Rotenona [Spanish], Foliafume, Nusyn, Protax, MFCD09025614, 5'.beta.-Rotenone, CAS-83-79-4, (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,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, (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, SR-01000076110, Cuberol, Rotenoid, Roteonone, Derri, Sinid, ChemFish, ChemMite, Derris powder, FishTox, DriKil, Cibe Extract, WLN: T G5 D6 B666 CV HO MO POT&TT&J IY1&U1 SO1 TO1, ProNox fish, Fish Tox, PBNox, 5''beta-rotenone, 5'b-Rotenone, Rotenone commercial, Rotocide E.C., (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)-, (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aalphaH)-one, 1,2,12,12aalpha-tetrahydro-2alpha-isopropenyl-8,9-dimethoxy-, (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,12A.ALPHA)).-, (1)Benzopyrano[3,3-h](1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-.alpha.-iospropenyl-8,9-dimethoxy-, (12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano(3,4-b)furano (2,3-h)chroman-6-one, (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, (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, (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,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)(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,6aS,12aS)-, [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.)]-, [1]BENZOPYRANO[3,4-B]FURO[2,3-H][1]BENZOPYRAN-6(6AALPHAH)-ONE, 1,2,12,12AALPHA-TETRAHYDRO-2ALPHA-ISOPROPENYL-8,9-DIMETHOXY-, [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,12A.ALPHA]).-, [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)]-, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methyl-ethenyl)-(1)benzopyrano (3,4-b)furo(2,3-h)(1) benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methyl-ethenyl)-[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, Prestwick_542, Rotenone (7CI), Rotenone (Standard), TUBOTOXINE, Rotenone, >=95%, Spectrum_000065, Spectrum2_000457, Spectrum3_000158, Spectrum4_001638, Spectrum5_000455, Rotenone (ACGIH:OSHA), Lopac0_001112, SCHEMBL42253, BSPBio_001896, isopropenyl(dimethoxy)[?]one, KBioGR_002075, KBioSS_000465, SPECTRUM200013, DivK1c_000947, SPBio_000534, HMS502P09, HY-B1756R, KBio1_000947, KBio2_000465, KBio2_003033, KBio2_005601, KBio3_001116, inhibits NADH2 oxidation to NAD, NSC8505, NINDS_000947, HMS3263O06, (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6a.alpha.H)-one, 1,2,12,12a.alpha.-tetrahydro-2.alpha.-isopropenyl-8,9-dimethoxy-, (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-, (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,2.alpha.,6a.alpha.,12a.alpha.)-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(6a.alpha.H)-one, 1,2,12,12a.alpha.-tetrahydro-2.alpha.-isopropenyl-8,9-dimethoxy-, 2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-H]chromen-6(6ah)-one, (6R,-(6a.alpha.,12a.alpha.)-, BCP07278, HY-B1756, NSC-8505, TNP00301, Tox21_110819, Tox21_201904, Tox21_300695, Tox21_501112, BDBM50135527, CCG-39886, HB5398, LMPK12060007, AKOS004910398, Tox21_110819_1, CS-6067, DB11457, FR65511, LP01112, SDCCGMLS-0066415.P001, SDCCGSBI-0051081.P003, IDI1_000947, Rotenone 100 microg/mL in Acetonitrile, USEPA/OPP Pesticide Code: 071003, 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, EU-0101112, NS00007117, R0090, Rotenone, PESTANAL(R), analytical standard, C07593, R 8875, HYDRO-2-ALPHA-ISOPROPENYL-8,9-DIMETHOXY-, Q412388, SR-01000076110-2, SR-01000076110-5, SR-01000076110-6, BRD-K08316444-001-01-9, BRD-K08316444-001-05-0, 1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, 1,2,12,12AALPHA-TETRAHYDRO-2A-ISOPROPENYL-8,9-DIMETHOXY, (1)BENZOPYRANO(3,4-B)FURO(2,3-H)(1)BENZOPYRAN-6(6AH)-ONE, 1,2,12,12A-TETRA-, (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))-, (1)BENZOPYRANO(3,4-B)FURO(2,3-H)(1)BENZOPYRAN-6(6ALPHAH)-ONE, 1,2,12,12AALPHA-TETRAHYDRO-2ALPHA-ISOPROPENYL-8,9-DIMETHOXY-, (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-(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-2-ALPHA-ISOPROPENYL-8,9-DIMETHOXY(1)BENZOPYRANO-(3,4-B)FURO(2,3-H)(1)BENZOPYRAN-6(6AH)-ONE, 1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methyl-ethenyl)-benzopyrano furo 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, 2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno(3,4-b)furo(2,3-H)chromen-6(6ah)-one, (6R,-(6aalpha,12aalpha)-, 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
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 63.2
Hydrogen Bond Donor Count 0.0
Pfizer 3 75 Rule False
Scaffold Graph Level CC1C2CCC3CCCC3C2CC2CCC3CCCCC3C21
Np Classifier Class Rotenoids
Deep Smiles COcccccc6OC))))OC[C@@H][C@H]6C=O)ccO6)cC[C@@H]Oc5cc9))))C=C)C
Heavy Atom Count 29.0
Classyfire Class Isoflavonoids
Description 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.
Scaffold Graph Node Level OC1C2CCC3OCCC3C2OC2COC3CCCCC3C21
Classyfire Subclass Rotenoids
Isotope Atom Count 0.0
Molecular Complexity 664.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 3.0
Uniprot Id P03905, P52505, n.a., Q72547, Q92887, Q54A96, P28272, P02545, P46063, B2RXH2, P51151, Q16637, P02791, P16473, P42345, Q9NUW8, P25779, P33261, P10636, P51450, P00352, Q01453, P97697, Q194T2, P15917, O15118, P54132, P06746, Q6W5P4, P08684, O75496, P11712, Q16236, Q99549, Q96KQ7, O15648, P83916, Q96QE3, P19793, Q99700, P10275, P10828, O89049, P49798, Q9UNA4, Q12809, Q03181, P03372, P37231, P04150, O94782, P50406, P25094, P04637, O42275, P81908, P03887, O46521, P00591, Q9Y6L6, Q9NPD5, Q9EPQ1, O95342, O15438, O15439, P0DTD1, P04792, P19838, P05412
Iupac Name (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
Prediction Hob 1.0
Class Isoflavonoids
Veber Rule True
Classyfire Superclass Phenylpropanoids and polyketides
Target Id NPT4266, NPT483, NPT47, NPT48, NPT537, NPT93, NPT210, NPT940, NPT50, NPT213, NPT51, NPT94, NPT796, NPT538, NPT58, NPT59, NPT1416, NPT109, NPT10, NPT212, NPT294, NPT713
Xlogp 4.1
Superclass Phenylpropanoids and polyketides
Subclass Rotenoids
Gsk 4 400 Rule True
Molecular Formula C23H22O6
Scaffold Graph Node Bond Level O=C1c2ccc3c(c2OC2COc4ccccc4C12)CCO3
Prediction Swissadme 1.0
Inchi Key JUVIOZPCNVVQFO-HBGVWJBISA-N
Silicos It Class Poorly soluble
Fcsp3 0.3478260869565217
Logs -6.008
Rotatable Bond Count 3.0
State Solid
Logd 3.457
Synonyms (-)-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, 5'beta-Rotenone, 5'b-Rotenone, 5'Β-rotenone, [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, Derris, jmaf, 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, rotenone
Esol Class Moderately soluble
Functional Groups C=C(C)C, cC(C)=O, cOC
Compound Name Rotenone
Kingdom Organic compounds
Prediction Hob Swissadme 1.0
Exact Mass 394.142
Formal Charge 0.0
Monoisotopic Mass 394.142
Hydrogen Bond Acceptor Count 6.0
Molecular Weight 394.4
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 3.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteropolycyclic compounds
Lipinski Rule Of 5 True
Esol -4.976629496551724
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
Smiles CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC
Nring 5.0
Np Classifier Biosynthetic Pathway Shikimates and Phenylpropanoids
Defined Bond Stereocenter Count 0.0
Egan Rule True
Taxonomy Direct Parent Rotenones
Np Classifier Superclass Isoflavonoids