IMPPAT Phytochemical information: 
Benzoic acid, 2-((1-oxo-1H-2-benzopyran-3-yl)methyl)-
Benzoic acid, 2-((1-oxo-1H-2-benzopyran-3-yl)methyl)-
Summary

SMILES: OC(=O)c1ccccc1Cc1cc2ccccc2c(=O)o1
InChI: InChI=1S/C17H12O4/c18-16(19)14-7-3-1-5-11(14)9-13-10-12-6-2-4-8-15(12)17(20)21-13/h1-8,10H,9H2,(H,18,19)
InChIKey: GCFOLLWPQAGLCM-UHFFFAOYSA-N
DeepSMILES: OC=O)cccccc6Ccccccccc6c=O)o%10
Scaffold Graph/Node/Bond level: O=c1oc(Cc2ccccc2)cc2ccccc12
Scaffold Graph/Node level: OC1OC(CC2CCCCC2)CC2CCCCC21
Scaffold Graph level: CC1CC(CC2CCCCC2)CC2CCCCC12
Functional groups: cC(=O)O; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isocoumarins and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Isocoumarins
Synonymous chemical names:
3-(but-trans-1-ynyl)-isocoumarin
External chemical identifiers:
CID:CID_197836
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Benzoic acid, 2-((1-oxo-1H-2-benzopyran-3-yl)methyl)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 280.28
Log P RDKit 3.08
Topological polar surface area (Å2) RDKit 67.51
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 21
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 16
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.06
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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
Benzoic acid, 2-((1-oxo-1H-2-benzopyran-3-yl)methyl)-
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 0.800183
Benzoic acid, 2-((1-oxo-1H-2-benzopyran-3-yl)methyl)-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.62
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