IMPPAT Phytochemical information: 
Oxyacanthan-12'-ol, 6',7-epoxy-6-methoxy-2,2'-dimethyl-, (1'alpha)-

Oxyacanthan-12'-ol, 6',7-epoxy-6-methoxy-2,2'-dimethyl-, (1'alpha)-
Summary

SMILES: COc1cc2CCN([C@@H]3c2c2c1Oc1cc4CCN([C@H](c4cc1O2)Cc1ccc(c(Oc2ccc(C3)cc2)c1)O)C)C
InChI: InChI=1S/C35H34N2O5/c1-36-12-10-22-17-30-31-19-25(22)26(36)15-21-6-9-28(38)29(16-21)40-24-7-4-20(5-8-24)14-27-33-23(11-13-37(27)2)18-32(39-3)34(41-30)35(33)42-31/h4-9,16-19,26-27,38H,10-15H2,1-3H3/t26-,27-/m0/s1
InChIKey: GOYCVNCWKXBQBF-SVBPBHIXSA-N
DeepSMILES: COcccCCN[C@@H]c6cc%10OcccCCN[C@H]c6cc%10O%14))))CcccccOccccC%24)cc6)))))))c6))O)))))))C))))))))))))C
Scaffold Graph/Node/Bond level: c1cc2cc(c1)Oc1ccc(cc1)CC1NCCc3ccc4c(c31)Oc1cc3c(cc1O4)CCNC3C2
Scaffold Graph/Node level: C1CC2CC(C1)OC1CCC(CC1)CC1NCCC3CCC4OC5CC6CCNC(C2)C6CC5OC4C31
Scaffold Graph level: C1CC2CC3CCC(CC3)CC3CCCC4CCC5CC6CC7CCCC(CC(C1)C2)C7CC6CC5C43
Functional groups: cOC; CN(C)C; cO; cOc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
cocsuline, cocsulin
External chemical identifiers:
CID:CID_21579625; ChEMBL:CHEMBL447886; SureChEMBL:SCHEMBL16251978
Chemical structure download


Oxyacanthan-12'-ol, 6',7-epoxy-6-methoxy-2,2'-dimethyl-, (1'alpha)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 562.67
Log P RDKit 6.95
Topological polar surface area (Å2) RDKit 63.63
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.31
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 9
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 9


Oxyacanthan-12'-ol, 6',7-epoxy-6-methoxy-2,2'-dimethyl-, (1'alpha)-
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
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 0.23727


Oxyacanthan-12'-ol, 6',7-epoxy-6-methoxy-2,2'-dimethyl-, (1'alpha)-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.47
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No