IMPPAT Phytochemical information: 
Gelselegine

Gelselegine
Summary

SMILES: CON1c2ccccc2[C@@]2(C1=O)C[C@H]1[C@H]3CO[C@@H]2C[C@H]3[C@](N1C)(CC)CO
InChI: InChI=1S/C21H28N2O4/c1-4-20(12-24)15-9-18-21(10-17(22(20)2)13(15)11-27-18)14-7-5-6-8-16(14)23(26-3)19(21)25/h5-8,13,15,17-18,24H,4,9-12H2,1-3H3/t13-,15+,17-,18+,20-,21-/m0/s1
InChIKey: OSYOERKDINCIMG-IKMCGIAPSA-N
DeepSMILES: CONcccccc6[C@@]C9=O))C[C@H][C@H]CO[C@@H]7C[C@H]6[C@]N9C))CC))CO
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C12CC1NCC3CC2OCC31
Scaffold Graph/Node level: OC1NC2CCCCC2C12CC1NCC3CC2OCC31
Scaffold Graph level: CC1CC2CCCCC2C12CC1CCC3CC2CCC31
Functional groups: cN(OC)C(=O)C; COC; CN(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Gelsemium alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
Synonymous chemical names:
Gelselegine, gelselegine
External chemical identifiers:
CID:CID_102061673
Chemical structure download


Gelselegine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 372.47
Log P RDKit 1.71
Topological polar surface area (Å2) RDKit 62.24
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Gelselegine
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 0.88


Gelselegine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.49
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