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Deguelin

PubChem CID: 107935

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Compound Synonyms Deguelin, 522-17-8, (-)-Deguelin, (-)-cis-deguelin, DEGUELIN(-), CHEBI:4357, MFCD01740600, K5Z93K66IE, (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-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, (7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one., Tocris-1770, SR-01000597503, UNII-K5Z93K66IE, (-)-Deguelin, (-)-cis-Deguelin, Legumelin, CCRIS 8104, Deguelin (6CI), Spectrum_001044, DEGUELIN [MI], Spectrum2_000298, Spectrum3_001122, Spectrum4_001965, Spectrum5_001852, SCHEMBL73183, BSPBio_002583, KBioGR_002434, KBioSS_001524, SPECTRUM201138, MLS006010295, SPBio_000236, CHEMBL393417, KBio2_001524, KBio2_004092, KBio2_006660, KBio3_002083, 12-alpha-Deoxytephrosin, Dequelin, DTXSID10200231, 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, BDBM50505204, CCG-39856, LMPK12060019, s8132, AKOS024456769, BCP9000596, CS-1802, FD65404, SDCCGMLS-0066380.P001, NCGC00025288-01, NCGC00025288-02, NCGC00025288-03, (-)-Deguelin, >98% (HPLC), powder, (7as,13as)-13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-3h-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-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, (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, 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)-
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 CC1C2CCC3CCCCC3C2CC2CCC3CCCCC3C21
Np Classifier Class Isoflavanones, Rotenoids
Deep Smiles COcccccc6OC))))OC[C@@H][C@H]6C=O)ccO6)cC=CCOc6cc%10))))C)C
Heavy Atom Count 29.0
Classyfire Class Isoflavonoids
Description 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.
Scaffold Graph Node Level OC1C2CCC3OCCCC3C2OC2COC3CCCCC3C21
Classyfire Subclass Rotenoids
Isotope Atom Count 0.0
Molecular Complexity 674.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 2.0
Uniprot Id P16473, P10636, P25779, P33261, P51450, Q9F4F7, P15917, P04637, P10635, P08684, P05177, Q9HC16, O94782, n.a., O42275, P81908, Q9NUW8, Q9Y6L6, Q9NPD5, P27695, Q16665, P08238, P06276, P22303, P07900
Iupac Name (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
Prediction Hob 1.0
Class Isoflavonoids
Veber Rule True
Classyfire Superclass Phenylpropanoids and polyketides
Target Id NPT210, NPT51, NPT213, NPT539, NPT110, NPT109, NPT208, NPT204, NPT918
Xlogp 3.7
Superclass Phenylpropanoids and polyketides
Subclass Rotenoids
Gsk 4 400 Rule False
Molecular Formula C23H22O6
Scaffold Graph Node Bond Level O=C1c2ccc3c(c2OC2COc4ccccc4C12)C=CCO3
Prediction Swissadme 1.0
Inchi Key ORDAZKGHSNRHTD-UXHICEINSA-N
Silicos It Class Moderately soluble
Fcsp3 0.3478260869565217
Logs -4.59
Rotatable Bond Count 2.0
Logd 4.055
Synonyms 13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7ah)-one, (-)-cis-Deguelin, deguelin
Esol Class Moderately soluble
Functional Groups cC(C)=O, cC=CC, cOC
Compound Name Deguelin
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 2.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteropolycyclic compounds
Lipinski Rule Of 5 True
Esol -4.803229496551725
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
Smiles CC1(C=CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC)C
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

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