IMPPAT Phytochemical information: 
(2R,3R,12bR)-3-ethenyl-9-methoxy-2-[[(1R)-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
(2R,3R,12bR)-3-ethenyl-9-methoxy-2-[[(1R)-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
Summary

SMILES: COc1ccc2c(c1)c1CCN[C@@H](c1[nH]2)C[C@@H]1C[C@H]2N(C[C@@H]1C=C)CCc1c2[nH]c2c1cc(cc2)OC
InChI: InChI=1S/C31H36N4O2/c1-4-18-17-35-12-10-23-25-16-21(37-3)6-8-27(25)34-31(23)29(35)14-19(18)13-28-30-22(9-11-32-28)24-15-20(36-2)5-7-26(24)33-30/h4-8,15-16,18-19,28-29,32-34H,1,9-14,17H2,2-3H3/t18-,19+,28+,29+/m0/s1
InChIKey: MKRBLBZRPCFROB-IUSJDPGBSA-N
DeepSMILES: COcccccc6)cCCN[C@@H]c6[nH]9))C[C@@H]C[C@H]NC[C@@H]6C=C))))CCcc6[nH]cc5cccc6))OC
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C(CC1CCN2CCc4c([nH]c5ccccc45)C2C1)NCC3
Scaffold Graph/Node level: C1CCC2C(C1)NC1C(CC3CCN4CCC5C6CCCCC6NC5C4C3)NCCC21
Scaffold Graph level: C1CCC2C(C1)CC1C(CC3CCC4CCC5C6CCCCC6CC5C4C3)CCCC21
Functional groups: cOC; CNC; c[nH]c; CN(C)C; C=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Harmala alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
cinchophyllamine, 3α, 17β-cinchophylline, 3-beta,17-beta-cinchophylline, 3-alpha,17-beta-cinchophylline, cinchophylline
External chemical identifiers:
CID:CID_165871
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2R,3R,12bR)-3-ethenyl-9-methoxy-2-[[(1R)-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 496.66
Log P RDKit 5.66
Topological polar surface area (Å2) RDKit 65.31
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
(2R,3R,12bR)-3-ethenyl-9-methoxy-2-[[(1R)-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
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 0.31
(2R,3R,12bR)-3-ethenyl-9-methoxy-2-[[(1R)-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.87
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No