IMPPAT Phytochemical information: 
methyl 2-(4-chloro-1H-indol-3-yl)acetate

methyl 2-(4-chloro-1H-indol-3-yl)acetate
Summary

SMILES: COC(=O)Cc1c[nH]c2c1c(Cl)ccc2
InChI: InChI=1S/C11H10ClNO2/c1-15-10(14)5-7-6-13-9-4-2-3-8(12)11(7)9/h2-4,6,13H,5H2,1H3
InChIKey: SYPGJEURLIGNPE-UHFFFAOYSA-N
DeepSMILES: COC=O)Ccc[nH]cc5cCl)ccc6
Scaffold Graph/Node/Bond level: c1ccc2[nH]ccc2c1
Scaffold Graph/Node level: C1CCC2NCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: COC(C)=O; c[nH]c; cCl
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indolyl carboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
methyl-4-chloroindole-3-acetate
External chemical identifiers:
CID:CID_161268; ZINC:ZINC000005997103; FDASRS:J94KP69SZB; SureChEMBL:SCHEMBL152993; MolPort-035-680-272
Chemical structure download


methyl 2-(4-chloro-1H-indol-3-yl)acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 223.66
Log P RDKit 2.54
Topological polar surface area (Å2) RDKit 42.09
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
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 9
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.18
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


methyl 2-(4-chloro-1H-indol-3-yl)acetate
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 0.8


methyl 2-(4-chloro-1H-indol-3-yl)acetate
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 -5.91
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No