IMPPAT Phytochemical information: 
4,21-Dehydrogeissoschizine

4,21-Dehydrogeissoschizine
Summary

SMILES: COC(=O)/C(=C\O)/[C@H]1C[C@@H]2[N+](=C/C/1=C/C)CCc1c2[nH]c2c1cccc2
InChI: InChI=1S/C21H22N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,11-12,16,19,22H,8-10H2,1-2H3/p+1/b13-3-/t16-,19-/m0/s1
InChIKey: CUHFIPBCFIPFJM-JXSBNBLESA-O
DeepSMILES: COC=O)/C=C\O))/[C@H]C[C@@H][N+]=C/C/6=C/C))))CCcc6[nH]cc5cccc6
Scaffold Graph/Node/Bond level: C=C1C=[N+]2CCc3c([nH]c4ccccc34)C2CC1
Scaffold Graph/Node level: CC1CCC2C3NC4CCCCC4C3CCN2C1
Scaffold Graph level: CC1CCC2C(CCC3C4CCCCC4CC23)C1
Functional groups: COC(=O)/C(C)=C\O; C/C=C(\C)C=[N+](C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyridoindoles
Synonymous chemical names:
4,21-dehydrogeissoschizine
External chemical identifiers:
CID:CID_5280619; ChEBI:CHEBI:17294; ZINC:ZINC000100066744; SureChEMBL:SCHEMBL23658250
Chemical structure download


4,21-Dehydrogeissoschizine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 351.43
Log P RDKit 3.43
Topological polar surface area (Å2) RDKit 65.33
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
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 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


4,21-Dehydrogeissoschizine
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 0.377019


4,21-Dehydrogeissoschizine
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 -6.53
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 3
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