Compound: Deguelin
SMILES: O=C1c2c(O[C@H]3[C@@H]1c4c(OC3)cc(OC)c(c4)OC)c5c(OC(C)(C)C=C5)cc2
InChIKey: ORDAZKGHSNRHTD-UXHICEINSA-N
Synonyms: Deguelin, 522-17-8, (-)-cis-deguelin, CHEBI:4357, K5Z93K66IE, DTXSID10200231, (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one, (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo(12.8.0.03,12.04,9.015,20)docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one, RefChem:919766, DTXCID10122722, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, (7aS-cis)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, (-)-Deguelin, DEGUELIN(-), MFCD01740600, (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one, C23H22O6, Tocris-1770, SR-01000597503, UNII-K5Z93K66IE, (-)-Deguelin;(-)-cis-Deguelin, Dequelin, Legumelin, CCRIS 8104, Deguelin (6CI), Spectrum_001044, 12-alpha-Deoxytephrosin, DEGUELIN [MI], Spectrum2_000298, Spectrum3_001122, Spectrum4_001965, Spectrum5_001852, GlyTouCan:G15155WL, SCHEMBL73183, BSPBio_002583, KBioGR_002434, KBioSS_001524, SPECTRUM201138, MLS006010295, SPBio_000236, CHEMBL393417, orb1300439, SCHEMBL29405854, SCHEMBL30910172, KBio2_001524, KBio2_004092, KBio2_006660, KBio3_002083, HMS1923A05, HMS3268E12, 3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS-cis)-, EX-A4158, G15155WL, BDBM50505204, CCG-39856, LMPK12060019, s8132, AKOS024456769, CS-1802, EBC-220093, FD65404, SDCCGMLS-0066380.P001, NCGC00025288-01, NCGC00025288-02, NCGC00025288-03, (-)-Deguelin, >98% (HPLC), powder, (7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one., AC-35505, AS-56004, HY-13425, SMR004701363, D5646, Q5251862, SR-01000597503-1, SR-01000597503-3, SR-01000597503-4, BRD-K61401890-001-02-0, BRD-K61401890-001-03-8, BRD-K61401890-001-04-6, (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15,17,19-heptaen-13-one, (7AS,13AS)-13,13A-DIHYDRO-9,10-DIMETHOXY-3,3-DIMETHYL-3H-(1)BENZOPYRANO(3,4-B)PYRANO(2,3-H)(1)BENZOPYRAN-7(7AH)-ONE, (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H,7aH-pyrano[2,3-c;6,5-f']dichromen-7-one, (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-[1]benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aH)-one, 13,13aS-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-[1]benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aS)-one, 3H-[1]Benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)-, 3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)-
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: 2
heavy_atom_count: 29
topological_polar_surface_area: 63.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Deguelin is a rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers. It has a role as an antiviral agent, an antineoplastic agent, a mitochondrial NADH:ubiquinone reductase inhibitor, an angiogenesis inhibitor, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, an anti-inflammatory agent, an apoptosis inducer and a plant metabolite. It is an aromatic ether, an organic heteropentacyclic compound, a diether and a member of rotenones.
chebi: A rotenone that is 13,13a-dihydro-3<em>H</em>-chromeno[3,4-<em>b</em>]pyrano[2,3-<em>h</em>]chromen-7(7a<em>H</em>)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7a<i>S</i>,13a<i>S</i>-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.
chembl: DEGUELIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Deguelin is a derivative of rotenone.  Both are compounds classified as rotenoids of the flavonoid family and are naturally occurring insecticides.  They can be produced by extraction from several plant species belonging to three genera of the legume family, Fabaceae: Lonchocarpus, Derris, or Tephrosia.
Cubé resin, the root extract from cubé (Lonchocarpus utilis) and from barbasco (Lonchocarpus urucu), is used as a commercial insecticide and piscicide (fish poison). The major active ingredients are rotenone and deguelin.  Although "organic" (produced by nature) cubé resin is no longer considered environmentally safe.