IMPPAT Phytochemical information: 
21-Oxogelsemine
21-Oxogelsemine
Summary

SMILES: C=C[C@@]12[C@@H]3C[C@@H]4[C@@]5([C@H]2[C@@H]([C@H]3CO4)N(C1=O)C)C(=O)Nc1c5cccc1
InChI: InChI=1S/C20H20N2O3/c1-3-19-12-8-14-20(11-6-4-5-7-13(11)21-17(20)23)16(19)15(10(12)9-25-14)22(2)18(19)24/h3-7,10,12,14-16H,1,8-9H2,2H3,(H,21,23)/t10-,12+,14+,15+,16-,19-,20-/m0/s1
InChIKey: WOURMHFKVOXOOP-MWBSSGTNSA-N
DeepSMILES: C=C[C@][C@@H]C[C@@H][C@@][C@H]6[C@@H][C@H]7CO7)))NC9=O))C))))C=O)Ncc5cccc6
Scaffold Graph/Node/Bond level: O=C1NC2C3COC4CC3C1C2C41C(=O)Nc2ccccc21
Scaffold Graph/Node level: OC1NC2C3COC4CC3C1C2C41C(O)NC2CCCCC21
Scaffold Graph level: CC1CC2C3CCC4CC3C1C2C41C(C)CC2CCCCC21
Functional groups: C=CC; COC; CN(C)C(=O)C; cNC(=O)C
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
NP Classifier Class: Corynanthe type
Synonymous chemical names:
21-oxo-gelsemine
External chemical identifiers:
CID:CID_11078214; ChEMBL:CHEMBL476882; ZINC:ZINC000040916331
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
21-Oxogelsemine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 336.39
Log P RDKit 1.55
Topological polar surface area (Å2) RDKit 58.64
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 3
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 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
21-Oxogelsemine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.791922
21-Oxogelsemine
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 -7.68
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes