IMPPAT Phytochemical information: 
Benzofuran

Benzofuran
Summary

SMILES: c1ccc2c(c1)occ2
InChI: InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
InChIKey: IANQTJSKSUMEQM-UHFFFAOYSA-N
DeepSMILES: cccccc6)occ5
Scaffold Graph/Node/Bond level: c1ccc2occc2c1
Scaffold Graph/Node level: C1CCC2OCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzofurans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Furocoumarins
Synonymous chemical names:
Benzofuran, benzofuran
External chemical identifiers:
CID:CID_9223; ChEMBL:CHEMBL363614; ChEBI:CHEBI:35260; ZINC:ZINC000001591814; FDASRS:LK6946W774; SureChEMBL:SCHEMBL5564; MolPort-000-145-910
Chemical structure download


Benzofuran
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 118.14
Log P RDKit 2.43
Topological polar surface area (Å2) RDKit 13.14
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 9
Number of heteroatoms RDKit 1
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 8
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


Benzofuran
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 3
Ghose filter RDKit Failed
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 0.517424


Benzofuran
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 -5.12
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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


Benzofuran
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000296946T800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.