IMPPAT Phytochemical information: 
8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one
8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one
Summary

SMILES: O=c1ccc2c(o1)c1OCOc1cc2
InChI: InChI=1S/C10H6O4/c11-8-4-2-6-1-3-7-10(9(6)14-8)13-5-12-7/h1-4H,5H2
InChIKey: OZRUEXJYRHKIJC-UHFFFAOYSA-N
DeepSMILES: O=ccccco6)cOCOc5cc9
Scaffold Graph/Node/Bond level: O=c1ccc2ccc3c(c2o1)OCO3
Scaffold Graph/Node level: OC1CCC2CCC3OCOC3C2O1
Scaffold Graph level: CC1CCC2CCC3CCCC3C2C1
Functional groups: 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:
7,8-methylene ether-7,8-dihydroxy-2h-benzopyran-2-one
External chemical identifiers:
CID:CID_13704003; ChEMBL:CHEMBL611651; ChEBI:CHEBI:173903; ZINC:ZINC000013481657; SureChEMBL:SCHEMBL6778388
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 190.15
Log P RDKit 1.52
Topological polar surface area (Å2) RDKit 48.67
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 4
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 1
Shape complexity RDKit 0.1
Number of rotatable bonds RDKit 0
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
8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one
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 0.59
8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one
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 -6.24
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