IMPPAT Phytochemical information: 
Macelignan

Macelignan
Summary

SMILES: COc1cc(ccc1O)C[C@@H]([C@@H](Cc1ccc2c(c1)OCO2)C)C
InChI: InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1
InChIKey: QDDILOVMGWUNGD-UONOGXRCSA-N
DeepSMILES: COcccccc6O))))C[C@@H][C@@H]Ccccccc6)OCO5)))))))))C))C
Scaffold Graph/Node/Bond level: c1ccc(CCCCc2ccc3c(c2)OCO3)cc1
Scaffold Graph/Node level: C1CCC(CCCCC2CCC3OCOC3C2)CC1
Scaffold Graph level: C1CCC(CCCCC2CCC3CCCC3C2)CC1
Functional groups: cOC; cO; 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:
Macelignan, macelignan
External chemical identifiers:
CID:CID_10404245; ChEMBL:CHEMBL254071; ChEBI:CHEBI:94153; ZINC:ZINC000013108863; FDASRS:8PP3614Z43; SureChEMBL:SCHEMBL1783132; MolPort-020-005-700
Chemical structure download


Macelignan
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 328.41
Log P RDKit 4.19
Topological polar surface area (Å2) RDKit 47.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
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 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
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


Macelignan
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 0.863712


Macelignan
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 -4.64
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 No
P-glycoprotein substrate SwissADME No