IMPPAT Phytochemical information: 
Machilin A
Machilin A
Summary

SMILES: C[C@H]([C@@H](Cc1ccc2c(c1)OCO2)C)Cc1ccc2c(c1)OCO2
InChI: InChI=1S/C20H22O4/c1-13(7-15-3-5-17-19(9-15)23-11-21-17)14(2)8-16-4-6-18-20(10-16)24-12-22-18/h3-6,9-10,13-14H,7-8,11-12H2,1-2H3/t13-,14+
InChIKey: QEFJURUMSHPMTC-OKILXGFUSA-N
DeepSMILES: C[C@H][C@@H]Ccccccc6)OCO5)))))))))C))Ccccccc6)OCO5
Scaffold Graph/Node/Bond level: c1cc2c(cc1CCCCc1ccc3c(c1)OCO3)OCO2
Scaffold Graph/Node level: C(CCC1CCC2OCOC2C1)CC1CCC2OCOC2C1
Scaffold Graph level: C(CCC1CCC2CCCC2C1)CC1CCC2CCCC2C1
Functional groups: c1cOCO1
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:
machilin a
External chemical identifiers:
CID:CID_10359012; ChEMBL:CHEMBL261367
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Machilin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 326.39
Log P RDKit 4.2
Topological polar surface area (Å2) RDKit 36.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
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 5
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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Machilin 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 0.82496
Machilin A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.49
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 Yes
P-glycoprotein substrate SwissADME No