IMPPAT Phytochemical information: 
Methyl 1-methoxy-1H-indole-3-carboxylate

Methyl 1-methoxy-1H-indole-3-carboxylate
Summary

SMILES: COC(=O)c1cn(c2c1cccc2)OC
InChI: InChI=1S/C11H11NO3/c1-14-11(13)9-7-12(15-2)10-6-4-3-5-8(9)10/h3-7H,1-2H3
InChIKey: JAAYVMHPQAMBJS-UHFFFAOYSA-N
DeepSMILES: COC=O)ccncc5cccc6))))))OC
Scaffold Graph/Node/Bond level: c1ccc2[nH]ccc2c1
Scaffold Graph/Node level: C1CCC2NCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: cC(=O)OC; cn(OC)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indolecarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
phytoalexin, isoflavonoid phytoalexin
External chemical identifiers:
CID:CID_10465540; ChEMBL:CHEMBL318151; ZINC:ZINC000014517111; SureChEMBL:SCHEMBL1849453
Chemical structure download


Methyl 1-methoxy-1H-indole-3-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 205.21
Log P RDKit 1.49
Topological polar surface area (Å2) RDKit 40.46
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
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 1-methoxy-1H-indole-3-carboxylate
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 0.697178


Methyl 1-methoxy-1H-indole-3-carboxylate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.61
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