IMPPAT Phytochemical information: 
Dracunculin

Dracunculin
Summary

SMILES: COc1cc2ccc(=O)oc2c2c1OCO2
InChI: InChI=1S/C11H8O5/c1-13-7-4-6-2-3-8(12)16-9(6)11-10(7)14-5-15-11/h2-4H,5H2,1H3
InChIKey: GHIKZCCKJTXOGO-UHFFFAOYSA-N
DeepSMILES: COcccccc=O)oc6cc%10OCO5
Scaffold Graph/Node/Bond level: O=c1ccc2ccc3c(c2o1)OCO3
Scaffold Graph/Node level: OC1CCC2CCC3OCOC3C2O1
Scaffold Graph level: CC1CCC2CCC3CCCC3C2C1
Functional groups: cOC; c=O; coc; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
6-methoxy-7,8-methylene-dioxycoumarin
External chemical identifiers:
CID:CID_5319474; ZINC:ZINC000002566154
Chemical structure download


Dracunculin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 220.18
Log P RDKit 1.53
Topological polar surface area (Å2) RDKit 57.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 5
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 9
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.18
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Dracunculin
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.681892


Dracunculin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.44
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No