IMPPAT Phytochemical information: 
3-Benzylidenephthalide

3-Benzylidenephthalide
Summary

SMILES: O=C1O/C(=C/c2ccccc2)/c2c1cccc2
InChI: InChI=1S/C15H10O2/c16-15-13-9-5-4-8-12(13)14(17-15)10-11-6-2-1-3-7-11/h1-10H/b14-10+
InChIKey: YRTPZXMEBGTPLM-GXDHUFHOSA-N
DeepSMILES: O=CO/C=C/cccccc6)))))))/cc5cccc6
Scaffold Graph/Node/Bond level: O=C1OC(=Cc2ccccc2)c2ccccc21
Scaffold Graph/Node level: OC1OC(CC2CCCCC2)C2CCCCC12
Scaffold Graph level: CC1CC(CC2CCCCC2)C2CCCCC12
Functional groups: c/C=C1\ccC(=O)O1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isocoumarans
ClassyFire Subclass: Isobenzofuranones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Diazotetronic acids and derivatives
NP Classifier Class: Pulvinones
Synonymous chemical names:
benzylidenephthalide
External chemical identifiers:
CID:CID_700611; ChEMBL:CHEMBL1562463; ZINC:ZINC000000080734; FDASRS:C9E8S3AGYQ; SureChEMBL:SCHEMBL5433929; MolPort-002-507-944
Chemical structure download


3-Benzylidenephthalide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 222.24
Log P RDKit 3.36
Topological polar surface area (Å2) RDKit 26.3
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 2
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 15
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
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 2
Number of aromatic heterocycles RDKit 0
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


3-Benzylidenephthalide
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 0.691438


3-Benzylidenephthalide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -5.19
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No