IMPPAT Phytochemical information: 
8-Methoxy-6,7-methylenedioxycoumarin

8-Methoxy-6,7-methylenedioxycoumarin
Summary

SMILES: COc1c2OCOc2cc2c1oc(=O)cc2
InChI: InChI=1S/C11H8O5/c1-13-11-9-6(2-3-8(12)16-9)4-7-10(11)15-5-14-7/h2-4H,5H2,1H3
InChIKey: GDJFGAQXNUYMPM-UHFFFAOYSA-N
DeepSMILES: COccOCOc5ccc9oc=O)cc6
Scaffold Graph/Node/Bond level: O=c1ccc2cc3c(cc2o1)OCO3
Scaffold Graph/Node level: OC1CCC2CC3OCOC3CC2O1
Scaffold Graph level: CC1CCC2CC3CCCC3CC2C1
Functional groups: cOC; c1cOCO1; coc; c=O
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:
8-methoxy-6,7-methylenedioxy coumarin, 8-methoxy-6, 7-methylenedioxycoumarin
External chemical identifiers:
CID:CID_13704005; ChEMBL:CHEMBL596030; ZINC:ZINC000014776358
Chemical structure download


8-Methoxy-6,7-methylenedioxycoumarin
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


8-Methoxy-6,7-methylenedioxycoumarin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.68


8-Methoxy-6,7-methylenedioxycoumarin
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