IMPPAT Phytochemical information: 
Heterotropan

Heterotropan
Summary

SMILES: COc1cc(OC)c(cc1C1C(C)C(C1c1cc(OC)c(cc1OC)OC)C)OC
InChI: InChI=1S/C24H32O6/c1-13-14(2)24(16-10-20(28-6)22(30-8)12-18(16)26-4)23(13)15-9-19(27-5)21(29-7)11-17(15)25-3/h9-14,23-24H,1-8H3
InChIKey: WCERJEZPIONOJU-UHFFFAOYSA-N
DeepSMILES: COcccOC))ccc6CCC)CC4cccOC))ccc6OC))))OC)))))))C))))))OC
Scaffold Graph/Node/Bond level: c1ccc(C2CCC2c2ccccc2)cc1
Scaffold Graph/Node level: C1CCC(C2CCC2C2CCCCC2)CC1
Scaffold Graph level: C1CCC(C2CCC2C2CCCCC2)CC1
Functional groups: cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Cyclobutane lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Minor lignans|Neolignans
Synonymous chemical names:
acoradin, heterotropan
External chemical identifiers:
CID:CID_126324
Chemical structure download


Heterotropan
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 416.51
Log P RDKit 4.89
Topological polar surface area (Å2) RDKit 55.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 8
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 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Heterotropan
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.61


Heterotropan
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 -5.35
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No