IMPPAT Phytochemical information: 
n-[2-(1h-Indol-3-yl)ethyl]-n-methyl-2-(methylamino)benzamide
n-[2-(1h-Indol-3-yl)ethyl]-n-methyl-2-(methylamino)benzamide
Summary

SMILES: CNc1ccccc1C(=O)N(CCc1c[nH]c2c1cccc2)C
InChI: InChI=1S/C19H21N3O/c1-20-17-9-5-4-8-16(17)19(23)22(2)12-11-14-13-21-18-10-6-3-7-15(14)18/h3-10,13,20-21H,11-12H2,1-2H3
InChIKey: KDRYLUSBBOOWIC-UHFFFAOYSA-N
DeepSMILES: CNcccccc6C=O)NCCcc[nH]cc5cccc6)))))))))))C
Scaffold Graph/Node/Bond level: O=C(NCCc1c[nH]c2ccccc12)c1ccccc1
Scaffold Graph/Node level: OC(NCCC1CNC2CCCCC12)C1CCCCC1
Scaffold Graph level: CC(CCCC1CCC2CCCCC21)C1CCCCC1
Functional groups: cNC; cC(=O)N(C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzoic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
evodiamide
External chemical identifiers:
CID:CID_189454; ZINC:ZINC000005141033
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
n-[2-(1h-Indol-3-yl)ethyl]-n-methyl-2-(methylamino)benzamide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 307.4
Log P RDKit 3.52
Topological polar surface area (Å2) RDKit 48.13
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 3
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 15
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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
n-[2-(1h-Indol-3-yl)ethyl]-n-methyl-2-(methylamino)benzamide
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 0.76
n-[2-(1h-Indol-3-yl)ethyl]-n-methyl-2-(methylamino)benzamide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.34
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No