IMPPAT Phytochemical information: 
Meso-dihydroguaiaretic acid

Meso-dihydroguaiaretic acid
Summary

SMILES: COc1cc(ccc1O)C[C@H]([C@H](Cc1ccc(c(c1)OC)O)C)C
InChI: InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3/t13-,14+
InChIKey: ADFOLUXMYYCTRR-OKILXGFUSA-N
DeepSMILES: COcccccc6O))))C[C@H][C@H]Ccccccc6)OC)))O))))))C))C
Scaffold Graph/Node/Bond level: c1ccc(CCCCc2ccccc2)cc1
Scaffold Graph/Node level: C1CCC(CCCCC2CCCCC2)CC1
Scaffold Graph level: C1CCC(CCCCC2CCCCC2)CC1
Functional groups: cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Dibenzylbutane lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Dibenzylbutane lignans
Synonymous chemical names:
meso-dihydroguaiaretic acid
External chemical identifiers:
CID:CID_476856; ChEMBL:CHEMBL430464; ChEBI:CHEBI:68169; ZINC:ZINC000015052537; FDASRS:S81Z40PSJ4; SureChEMBL:SCHEMBL974725
Chemical structure download


Meso-dihydroguaiaretic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 330.42
Log P RDKit 4.17
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
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 12
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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


Meso-dihydroguaiaretic acid
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 0.799677


Meso-dihydroguaiaretic acid
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 -4.79
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes


Meso-dihydroguaiaretic acid
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000283916TMPRSS11D786
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.