IMPPAT Phytochemical information: 
Guaiacin

Guaiacin
Summary

SMILES: COc1cc2C[C@@H](C)[C@@H]([C@H](c2cc1O)c1ccc(c(c1)OC)O)C
InChI: InChI=1S/C20H24O4/c1-11-7-14-9-19(24-4)17(22)10-15(14)20(12(11)2)13-5-6-16(21)18(8-13)23-3/h5-6,8-12,20-22H,7H2,1-4H3/t11-,12+,20+/m1/s1
InChIKey: TZAAYUCUPIYQBR-JGRMJRGVSA-N
DeepSMILES: COcccC[C@@H]C)[C@@H][C@H]c6cc%10O))))cccccc6)OC)))O))))))C
Scaffold Graph/Node/Bond level: c1ccc(C2CCCc3ccccc32)cc1
Scaffold Graph/Node level: C1CCC(C2CCCC3CCCCC32)CC1
Scaffold Graph level: C1CCC(C2CCCC3CCCCC32)CC1
Functional groups: cOC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Aryltetralin lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
guaiacin
External chemical identifiers:
CID:CID_11724027; ChEMBL:CHEMBL1080351; ChEBI:CHEBI:68173; ZINC:ZINC000034646124; FDASRS:O8S88V2539; MolPort-039-338-380
Chemical structure download


Guaiacin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 328.41
Log P RDKit 4.08
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 3
Stereochemical complexity RDKit 0.15
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 3
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


Guaiacin
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 0.891328


Guaiacin
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 -5.12
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 No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No