IMPPAT Phytochemical information: 
Gelsemoxonine
Gelsemoxonine
Summary

SMILES: CON1c2ccccc2[C@@]2(C1=O)C[C@@H]1N[C@@]3([C@H]([C@H]2OC[C@H]13)O)C(=O)CC
InChI: InChI=1S/C19H22N2O5/c1-3-14(22)19-11-9-26-16(15(19)23)18(8-12(11)20-19)10-6-4-5-7-13(10)21(25-2)17(18)24/h4-7,11-12,15-16,20,23H,3,8-9H2,1-2H3/t11-,12+,15+,16-,18+,19-/m1/s1
InChIKey: KCKQVEIIPULRFW-SAAOQMMJSA-N
DeepSMILES: CONcccccc6[C@@]C9=O))C[C@@H]N[C@@][C@H][C@H]7OC[C@H]86))))O))C=O)CC
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C12CC1NC3CC2OCC31
Scaffold Graph/Node level: OC1NC2CCCCC2C12CC1NC3CC2OCC31
Scaffold Graph level: CC1CC2CCCCC2C12CC1CC3CC2CCC31
Functional groups: cN(OC)C(=O)C; CNC; COC; CO; CC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Strychnos type
Synonymous chemical names:
Gelsemoxonine, gelsemoxonine
External chemical identifiers:
CID:CID_44583831; ChEMBL:CHEMBL524079; ZINC:ZINC000040975655
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Gelsemoxonine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 358.39
Log P RDKit 0.3
Topological polar surface area (Å2) RDKit 88.1
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.58
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 5
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 0
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Gelsemoxonine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.81
Gelsemoxonine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.23
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 Yes