IMPPAT Phytochemical information: 
Indolo[2,3-a]quinolizine-2-acetic acid, 3-ethenyl-1,2,3,4,6,7,12,12b-octahydro-alpha-(methoxymethylene)-, methyl ester, (alphaE,2S,3R,12bS)-
Indolo[2,3-a]quinolizine-2-acetic acid, 3-ethenyl-1,2,3,4,6,7,12,12b-octahydro-alpha-(methoxymethylene)-, methyl ester, (alphaE,2S,3R,12bS)-
Summary

SMILES: CO/C=C(/[C@H]1C[C@@H]2N(C[C@@H]1C=C)CCc1c2[nH]c2c1cccc2)\C(=O)OC
InChI: InChI=1S/C22H26N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h4-8,13-14,17,20,23H,1,9-12H2,2-3H3/b18-13-/t14-,17-,20-/m0/s1
InChIKey: TZUGIFAYWNNSAO-CPHCKLLXSA-N
DeepSMILES: CO/C=C/[C@H]C[C@@H]NC[C@@H]6C=C))))CCcc6[nH]cc5cccc6)))))))))))))))\C=O)OC
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CCCCN1CC3
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCN2CCCCC12
Scaffold Graph level: C1CCC2C(C1)CC1C3CCCCC3CCC21
Functional groups: CO/C=C(/C)C(=O)OC; CN(C)C; C=CC; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Corynanthean-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
corynantheine
External chemical identifiers:
CID:CID_3000320; ZINC:ZINC000085909641; SureChEMBL:SCHEMBL3084853; MolPort-039-338-502
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Indolo[2,3-a]quinolizine-2-acetic acid, 3-ethenyl-1,2,3,4,6,7,12,12b-octahydro-alpha-(methoxymethylene)-, methyl ester, (alphaE,2S,3R,12bS)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 366.46
Log P RDKit 3.59
Topological polar surface area (Å2) RDKit 54.56
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.41
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Indolo[2,3-a]quinolizine-2-acetic acid, 3-ethenyl-1,2,3,4,6,7,12,12b-octahydro-alpha-(methoxymethylene)-, methyl ester, (alphaE,2S,3R,12bS)-
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.39
Indolo[2,3-a]quinolizine-2-acetic acid, 3-ethenyl-1,2,3,4,6,7,12,12b-octahydro-alpha-(methoxymethylene)-, methyl ester, (alphaE,2S,3R,12bS)-
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 -6.28
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No