IMPPAT Phytochemical information: 
Gelsevirine

Gelsevirine
Summary

SMILES: CON1c2ccccc2[C@]2(C1=O)[C@@H]1OC[C@@H]3[C@@H]4[C@H]2[C@@]([C@@H]3C1)(C=C)CN4C
InChI: InChI=1S/C21H24N2O3/c1-4-20-11-22(2)17-12-10-26-16(9-14(12)20)21(18(17)20)13-7-5-6-8-15(13)23(25-3)19(21)24/h4-8,12,14,16-18H,1,9-11H2,2-3H3/t12-,14+,16+,17+,18-,20-,21-/m0/s1
InChIKey: SSSCMFCWHWCCEH-MTYPYGCKSA-N
DeepSMILES: CONcccccc6[C@]C9=O))[C@@H]OC[C@@H][C@@H][C@H]7[C@@][C@@H]5C9))C=C))CN5C
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C12C1CC3C(CO1)C1NCC3C12
Scaffold Graph/Node level: OC1NC2CCCCC2C12C1CC3C(CO1)C1NCC3C12
Scaffold Graph level: CC1CC2CCCCC2C12C1CCC3C(C1)C1CCC3C12
Functional groups: cN(OC)C(=O)C; COC; C=CC; CN(C)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:
gelsevirine
External chemical identifiers:
CID:CID_14217344; ChEMBL:CHEMBL515314; ZINC:ZINC000040916683
Chemical structure download


Gelsevirine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.43
Log P RDKit 1.98
Topological polar surface area (Å2) RDKit 42.01
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
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 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 1
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


Gelsevirine
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 0.763631


Gelsevirine
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 -7.02
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 No