IMPPAT Phytochemical information: 
Ligustilide

Ligustilide
Summary

SMILES: CCC/C=C/1\OC(=O)C2=C1CCC=C2
InChI: InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3/b11-8-
InChIKey: IQVQXVFMNOFTMU-FLIBITNWSA-N
DeepSMILES: CCC/C=C\OC=O)C=C\5CCC=C6
Scaffold Graph/Node/Bond level: C=C1OC(=O)C2=C1CCC=C2
Scaffold Graph/Node level: CC1OC(O)C2CCCCC12
Scaffold Graph level: CC1CC(C)C2CCCCC12
Functional groups: C/C=C1\OC(=O)C2=C1CCC=C2
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isobenzofurans
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Cyclic polyketides
NP Classifier Class: Phthalide derivatives
Synonymous chemical names:
(Z)-ligustilide, z-lingustilide, z-ligustilide, ligustilide, (z)-ligustilide (2), ligustilide,z-
External chemical identifiers:
CID:CID_5319022; ChEMBL:CHEMBL481246; ChEBI:CHEBI:68232; ZINC:ZINC000002386261; FDASRS:10HE68JD06; SureChEMBL:SCHEMBL4087027; MolPort-003-665-830
Chemical structure download


Ligustilide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 190.24
Log P RDKit 2.87
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 12
Number of heavy atoms RDKit 14
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 7
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
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


Ligustilide
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 0.63


Ligustilide
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 -5.54
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


Ligustilide
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000369442KL800
ENSP00000287641SST846
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.