IMPPAT Phytochemical information: 
Pinoresinol
Pinoresinol
Summary

SMILES: COc1cc(ccc1O)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc(c(c1)OC)O
InChI: InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1
InChIKey: HGXBRUKMWQGOIE-AFHBHXEDSA-N
DeepSMILES: COcccccc6O))))[C@H]OC[C@H][C@@H]5CO[C@@H]5cccccc6)OC)))O
Scaffold Graph/Node/Bond level: c1ccc(C2OCC3C(c4ccccc4)OCC23)cc1
Scaffold Graph/Node level: C1CCC(C2OCC3C2COC3C2CCCCC2)CC1
Scaffold Graph level: C1CCC(C2CCC3C(C4CCCCC4)CCC23)CC1
Functional groups: cOC; cO; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Furanoid lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Furofuranoid lignans
Synonymous chemical names:
(+) pinoresinol, (+)pinoresinol, Pinoresinol, pinoresinol, (+)-pinoresinol
External chemical identifiers:
CID:CID_73399; ChEMBL:CHEMBL260183; ChEBI:CHEBI:40; ZINC:ZINC000004098921; FDASRS:V4N1UDY811; SureChEMBL:SCHEMBL122105; MolPort-001-740-983
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Pinoresinol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 358.39
Log P RDKit 3.19
Topological polar surface area (Å2) RDKit 77.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Pinoresinol
Drug-likeness
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 0.874053
Pinoresinol
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 -6.87
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes
Pinoresinol
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001851ENSG00000282607MGAM8972ChEMBL
TAR_EXP_001497ENSG00000090402SI6476ChEMBL
TAR_EXP_001306ENSG00000196396PTPN15770ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL
TAR_EXP_000711ENSG00000086696HSD17B23294ChEMBL, NPASS
TAR_EXP_001895ENSG00000257743MGAM293432ChEMBL
TAR_EXP_000519ENSG00000171298GAA2548ChEMBL