1.0 2010-04-08 22:06:45 UTC 2025-11-18 22:59:33 UTC FDB005595 Legumelin Legumelin, also known as (-)-cis-deguelin, is a member of the class of compounds known as rotenones. Rotenones are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. Thus, legumelin is considered to be a flavonoid lipid molecule. Legumelin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Legumelin can be found in soy bean, which makes legumelin a potential biomarker for the consumption of this food product. C23H22O6 394.423 394.141638428 (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 deguelin 522-17-8 [H][C@@]12COC3=CC(OC)=C(OC)C=C3[C@]1([H])C(=O)C1=C(O2)C2=C(OC(C)(C)C=C2)C=C1 InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1 ORDAZKGHSNRHTD-UXHICEINSA-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 2,2-dimethyl-1-benzopyrans 8-prenylated isoflavanones Alkyl aryl ethers Anisoles Aryl alkyl ketones Chromones Hydrocarbon derivatives Organic oxides Oxacyclic compounds Pyranochromenes 1-benzopyran 2,2-dimethyl-1-benzopyran 8-prenylated isoflavanone Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzopyran Chromane Chromone Ether Hydrocarbon derivative Isoflavan Isoflavanone Ketone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Pyranochromene Rotenone or derivatives Rotenoid flavonoids isoflavanones rotenones logp 3.93 ALOGPS logs -5.16 ALOGPS solubility 2.71e-03 g/l ALOGPS logp 3.3 ChemAxon pka_strongest_acidic 11.72 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (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 ChemAxon average_mass 394.423 ChemAxon mono_mass 394.141638428 ChemAxon smiles [H][C@@]12COC3=CC(OC)=C(OC)C=C3[C@]1([H])C(=O)C1=C(O2)C2=C(OC(C)(C)C=C2)C=C1 ChemAxon formula C23H22O6 ChemAxon inchi InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1 ChemAxon inchikey ORDAZKGHSNRHTD-UXHICEINSA-N ChemAxon polar_surface_area 63.22 ChemAxon refractivity 107.22 ChemAxon polarizability 42.12 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 107403 Specdb::MsMs 107404 Specdb::MsMs 107405 Specdb::MsMs 174384 Specdb::MsMs 174385 Specdb::MsMs 174386 Specdb::MsMs 3601934 Specdb::MsMs 3601935 Specdb::MsMs 3601936 Specdb::MsMs 3601937 Specdb::MsMs 3601938 Specdb::MsMs 3601939 Soy bean Type 1 specific Glycine max 3847