IMPPAT Phytochemical information: 
Dehydrodeguelin

Dehydrodeguelin
Summary

SMILES: COc1cc2-c3c(COc2cc1OC)oc1c(c3=O)ccc2c1C=CC(O2)(C)C
InChI: InChI=1S/C23H20O6/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/h5-10H,11H2,1-4H3
InChIKey: NGQVFILFHVPLFE-UHFFFAOYSA-N
DeepSMILES: COccc-ccCOc6cc%10OC)))))))occc6=O))cccc6C=CCO6)C)C
Scaffold Graph/Node/Bond level: O=c1c2c(oc3c4c(ccc13)OCC=C4)COc1ccccc1-2
Scaffold Graph/Node level: OC1C2CCC3OCCCC3C2OC2COC3CCCCC3C21
Scaffold Graph level: CC1C2CCC3CCCCC3C2CC2CCC3CCCCC3C21
Functional groups: cOC; coc; c=O; cC=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Rotenoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Rotenoids
Synonymous chemical names:
Dehydrodeguelin, dehydrodeguelin
External chemical identifiers:
CID:CID_3083803; ChEMBL:CHEMBL465673; ZINC:ZINC000013434200; SureChEMBL:SCHEMBL16694597; MolPort-039-141-929
Chemical structure download


Dehydrodeguelin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 392.41
Log P RDKit 4.55
Topological polar surface area (Å2) RDKit 67.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.26
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Dehydrodeguelin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.637233


Dehydrodeguelin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.14
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes