IMPPAT Phytochemical information: 
Dukunolide A

Dukunolide A
Summary

SMILES: O=C1OC2(C3(C1O3)C(C)(C)C(=O)C1(C2(O)C2=C3C(=CCCC3(C(OC2=O)c2cocc2)C)C1)O)C
InChI: InChI=1S/C26H26O9/c1-21(2)20(29)24(30)10-12-6-5-8-22(3)14(12)15(18(27)33-16(22)13-7-9-32-11-13)25(24,31)23(4)26(21)17(34-26)19(28)35-23/h6-7,9,11,16-17,30-31H,5,8,10H2,1-4H3
InChIKey: BATTZJIKLZSIAU-UHFFFAOYSA-N
DeepSMILES: O=COCCC5O3))CC)C)C=O)CC6O)C=CC=CCCC6COC%10=O)))ccocc5))))))C)))))C6)))))O)))))C
Scaffold Graph/Node/Bond level: O=C1OC(c2ccoc2)C2CCC=C3CC4C(=O)CC56OC5C(=O)OC6C4C1=C32
Scaffold Graph/Node level: OC1CC23OC2C(O)OC3C2C1CC1CCCC3C(C4CCOC4)OC(O)C2C13
Scaffold Graph level: CC1CC23CC2C(C)CC3C2C1CC1CCCC3C(C4CCCC4)CC(C)C2C13
Functional groups: CC12COC(=O)C1O2; CO; CC(=O)C; CC=C(C)C1=C(C)C(=O)OCC1; 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 a
External chemical identifiers:
CID:CID_73820465; ChEBI:CHEBI:172707
Chemical structure download


Dukunolide A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 482.49
Log P RDKit 1.83
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 7
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.58
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 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7


Dukunolide A
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 0.453764


Dukunolide A
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 -9.20
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes