IMPPAT Phytochemical information: 
Alkaloid C, from Gelsemium sempervirens

Alkaloid C, from Gelsemium sempervirens
Summary

SMILES: CCC1NC2C3C1C(O)C(C1(C2)c2ccc(cc2N(C1=O)OC)OC)OC3
InChI: InChI=1S/C20H26N2O5/c1-4-13-16-11-9-27-18(17(16)23)20(8-14(11)21-13)12-6-5-10(25-2)7-15(12)22(26-3)19(20)24/h5-7,11,13-14,16-18,21,23H,4,8-9H2,1-3H3
InChIKey: CWXVIZDGZSQOSO-UHFFFAOYSA-N
DeepSMILES: CCCNCCC5CO)CCC7)cccccc6NC9=O))OC)))))OC)))))))OC6
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C12CC1NCC3CC2OCC31
Scaffold Graph/Node level: OC1NC2CCCCC2C12CC1NCC3CC2OCC31
Scaffold Graph level: CC1CC2CCCCC2C12CC1CCC3CC2CCC31
Functional groups: CNC; CO; cN(OC)C(=O)C; cOC; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Gelsemium alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
14-oh-gelsemicine
External chemical identifiers:
CID:CID_597741
Chemical structure download


Alkaloid C, from Gelsemium sempervirens
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 374.44
Log P RDKit 0.99
Topological polar surface area (Å2) RDKit 80.26
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
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 7
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.65
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


Alkaloid C, from Gelsemium sempervirens
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.821358


Alkaloid C, from Gelsemium sempervirens
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 -7.93
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 Yes