IMPPAT Phytochemical information: 
Tepirindole

Tepirindole
Summary

SMILES: CCCN1CCC(=CC1)c1c[nH]c2c1cc(Cl)cc2
InChI: InChI=1S/C16H19ClN2/c1-2-7-19-8-5-12(6-9-19)15-11-18-16-4-3-13(17)10-14(15)16/h3-5,10-11,18H,2,6-9H2,1H3
InChIKey: ZRCUMOBNOPSLKM-UHFFFAOYSA-N
DeepSMILES: CCCNCCC=CC6))cc[nH]cc5ccCl)cc6
Scaffold Graph/Node/Bond level: C1=C(c2c[nH]c3ccccc23)CCNC1
Scaffold Graph/Node level: C1CCC2C(C1)NCC2C1CCNCC1
Scaffold Graph level: C1CCC(C2CCC3CCCCC32)CC1
Functional groups: CN(C)C; cC(=CC)C; c[nH]c; cCl
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
tepurindiol
External chemical identifiers:
CID:CID_68915; ChEMBL:CHEMBL2105413; FDASRS:X235XX30GK; SureChEMBL:SCHEMBL635174
Chemical structure download


Tepirindole
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 274.8
Log P RDKit 4.32
Topological polar surface area (Å2) RDKit 19.03
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Tepirindole
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.883092


Tepirindole
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.29
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes