IMPPAT Phytochemical information: 
Dukunolide E

Dukunolide E
Summary

SMILES: O=C1CC2C(O1)(C)C1(O)C3=C4C5(CC1(C(=O)C2(C)C)O)OC5CCC4(C(OC3=O)c1cocc1)C
InChI: InChI=1S/C26H28O9/c1-21(2)13-9-15(27)35-23(13,4)26(31)16-17-22(3,18(33-19(16)28)12-6-8-32-10-12)7-5-14-24(17,34-14)11-25(26,30)20(21)29/h6,8,10,13-14,18,30-31H,5,7,9,11H2,1-4H3
InChIKey: HQKQACOUFFEUAD-UHFFFAOYSA-N
DeepSMILES: O=CCCCO5)C)CO)C=CCCC6C=O)C%10C)C)))O)))OC3CCC7COC%11=O)))ccocc5))))))C
Scaffold Graph/Node/Bond level: O=C1CC2CC(=O)C3CC45OC4CCC4C5=C(C(=O)OC4c4ccoc4)C3C2O1
Scaffold Graph/Node level: OC1CC2CC(O)C3CC45OC4CCC4C(C6CCOC6)OC(O)C(C3C2O1)C45
Scaffold Graph level: CC1CC2CC(C)C3CC45CC4CCC4C(C6CCCC6)CC(C)C(C3C2C1)C45
Functional groups: COC(=O)C; CO; CC1=C(CCOC1=O)C1(C)OC1C; CC(=O)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
dukunolide e
External chemical identifiers:
CID:CID_131751857
Chemical structure download


Dukunolide E
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 484.5
Log P RDKit 1.91
Topological polar surface area (Å2) RDKit 135.8
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7


Dukunolide E
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 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.452436


Dukunolide E
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -9.35
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes