IMPPAT Phytochemical information: 
Licarin A

Licarin A
Summary

SMILES: C/C=C/c1cc2c(c(c1)OC)O[C@@H]([C@H]2C)c1ccc(c(c1)OC)O
InChI: InChI=1S/C20H22O4/c1-5-6-13-9-15-12(2)19(24-20(15)18(10-13)23-4)14-7-8-16(21)17(11-14)22-3/h5-12,19,21H,1-4H3/b6-5+/t12-,19-/m0/s1
InChIKey: ITDOFWOJEDZPCF-FNINDUDTSA-N
DeepSMILES: C/C=C/cccccc6)OC)))O[C@@H][C@H]5C))cccccc6)OC)))O
Scaffold Graph/Node/Bond level: c1ccc(C2Cc3ccccc3O2)cc1
Scaffold Graph/Node level: C1CCC(C2CC3CCCCC3O2)CC1
Scaffold Graph level: C1CCC(C2CC3CCCCC3C2)CC1
Functional groups: c/C=C/C; cOC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: 2-arylbenzofuran flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Neolignans
Synonymous chemical names:
dehydro diisoeugenol, licarin a, dehydrodiisoeugenol, Dehydrodiisoeugenol
External chemical identifiers:
CID:CID_5281836; ChEMBL:CHEMBL463526; ChEBI:CHEBI:6451; ZINC:ZINC000004098822; SureChEMBL:SCHEMBL2871101; MolPort-035-706-055
Chemical structure download


Licarin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 326.39
Log P RDKit 4.68
Topological polar surface area (Å2) RDKit 47.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 4
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


Licarin A
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.886022


Licarin A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -5.18
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No