IMPPAT Phytochemical information: 
Cissampareine
Cissampareine
Summary

SMILES: COc1cc2CCN=C3c2c(c1OCc1ccc(cc1)C[C@H]1N(C)CCc2c1c(Oc1ccc(C3)cc1)c(OC)c(c2)OC)O
InChI: InChI=1S/C37H38N2O6/c1-39-16-14-26-20-31(42-3)36(43-4)37-33(26)29(39)18-23-5-7-24(8-6-23)21-44-35-30(41-2)19-25-13-15-38-28(32(25)34(35)40)17-22-9-11-27(45-37)12-10-22/h5-12,19-20,29,40H,13-18,21H2,1-4H3/t29-/m1/s1
InChIKey: CXLYPEWFHWCEFN-GDLZYMKVSA-N
DeepSMILES: COcccCCN=Cc6cc%10OCcccccc6))C[C@H]NC)CCcc6cOccccC%24)cc6)))))))cOC))cc6)OC)))))))))))))))))))O
Scaffold Graph/Node/Bond level: c1cc2c3c(c1)Oc1ccc(cc1)CC1=NCCc4ccc(cc41)OCc1ccc(cc1)CC3NCC2
Scaffold Graph/Node level: C1CC2CCNC3CC4CCC(CC4)COC4CCC5CCNC(CC6CCC(CC6)OC(C1)C23)C5C4
Scaffold Graph level: C1CC2CCC3CCC4CCC(CC4)CC4CCCC5CCCC(CC6CCC(CC6)CC(C1)C2C3)C54
Functional groups: cOC; cC(=NC)C; cO; CN(C)C; cOc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Ethers
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
cissampareine, Cissampareine
External chemical identifiers:
CID:CID_254905; ChEMBL:CHEMBL2063771; ZINC:ZINC000060184488
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cissampareine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 606.72
Log P RDKit 6.46
Topological polar surface area (Å2) RDKit 81.98
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.03
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 25
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 3
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
Cissampareine
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 0.286642
Cissampareine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.93
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