IMPPAT Phytochemical information: 
Isotaxiresinol

Isotaxiresinol
Summary

SMILES: OC[C@@H]1Cc2cc(OC)c(cc2[C@@H]([C@H]1CO)c1ccc(c(c1)O)O)O
InChI: InChI=1S/C19H22O6/c1-25-18-6-11-4-12(8-20)14(9-21)19(13(11)7-17(18)24)10-2-3-15(22)16(23)5-10/h2-3,5-7,12,14,19-24H,4,8-9H2,1H3/t12-,14-,19-/m0/s1
InChIKey: GQLVRVYXAHDDLB-PJFSTRORSA-N
DeepSMILES: OC[C@@H]CcccOC))ccc6[C@@H][C@H]%10CO)))cccccc6)O))O))))))))O
Scaffold Graph/Node/Bond level: c1ccc(C2CCCc3ccccc32)cc1
Scaffold Graph/Node level: C1CCC(C2CCCC3CCCCC32)CC1
Scaffold Graph level: C1CCC(C2CCCC3CCCCC32)CC1
Functional groups: CO; cOC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Aryltetralin lignans
ClassyFire Subclass: 9,9p-dihydroxyaryltetralin lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
Isotaxiresinol, isotaxiresinol
External chemical identifiers:
CID:CID_9841162; ChEMBL:CHEMBL1668111; ChEBI:CHEBI:70194; ZINC:ZINC000014435203; SureChEMBL:SCHEMBL13475141; MolPort-005-945-644
Chemical structure download


Isotaxiresinol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 346.38
Log P RDKit 1.72
Topological polar surface area (Å2) RDKit 110.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.37
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
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


Isotaxiresinol
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.539285


Isotaxiresinol
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.19
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes