IMPPAT Phytochemical information: 
Geissoschizal

Geissoschizal
Summary

SMILES: O=CC[C@H]1C[C@@H]2N(C/C/1=C/C)CCc1c2[nH]c2c1cccc2
InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-9-7-16-15-5-3-4-6-17(15)20-19(16)18(21)11-14(13)8-10-22/h2-6,10,14,18,20H,7-9,11-12H2,1H3/b13-2-/t14-,18-/m0/s1
InChIKey: BPOHSWSDHJBBKX-VILUJCMCSA-N
DeepSMILES: O=CC[C@H]C[C@@H]NC/C/6=C/C))))CCcc6[nH]cc5cccc6
Scaffold Graph/Node/Bond level: C=C1CCC2c3[nH]c4ccccc4c3CCN2C1
Scaffold Graph/Node level: CC1CCC2C3NC4CCCCC4C3CCN2C1
Scaffold Graph level: CC1CCC2C(CCC3C4CCCCC4CC23)C1
Functional groups: CC=O; CN(C)C; C/C=C(/C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyridoindoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
geissoschizal
External chemical identifiers:
CID:CID_11022778; ZINC:ZINC000137481360
Chemical structure download


Geissoschizal
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 294.4
Log P RDKit 3.62
Topological polar surface area (Å2) RDKit 36.1
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 2
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Geissoschizal
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.68


Geissoschizal
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 -6.60
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
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