IMPPAT Phytochemical information: 
Gelsenicine

Gelsenicine
Summary

SMILES: CON1c2ccccc2[C@@]2(C1=O)C[C@@H]1N=C([C@@H]3C[C@H]2OC[C@H]13)CC
InChI: InChI=1S/C19H22N2O3/c1-3-14-11-8-17-19(9-15(20-14)12(11)10-24-17)13-6-4-5-7-16(13)21(23-2)18(19)22/h4-7,11-12,15,17H,3,8-10H2,1-2H3/t11-,12+,15+,17-,19+/m1/s1
InChIKey: BIGABVPVCRHEES-NWPJSNQLSA-N
DeepSMILES: CONcccccc6[C@@]C9=O))C[C@@H]N=C[C@@H]C[C@H]8OC[C@H]96))))))CC
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C12CC1N=CC3CC2OCC31
Scaffold Graph/Node level: OC1NC2CCCCC2C12CC1NCC3CC2OCC31
Scaffold Graph level: CC1CC2CCCCC2C12CC1CCC3CC2CCC31
Functional groups: cN(OC)C(=O)C; CC(=NC)C; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
Synonymous chemical names:
gelsenicine, Gelsenicine, humantenmine
External chemical identifiers:
CID:CID_21123652; ChEMBL:CHEMBL523429; ZINC:ZINC000031459051; MolPort-046-785-861
Chemical structure download


Gelsenicine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 326.4
Log P RDKit 2.49
Topological polar surface area (Å2) RDKit 51.13
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.26
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 1
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 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Gelsenicine
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 0.838881


Gelsenicine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -7.39
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 Yes
P-glycoprotein substrate SwissADME No