IMPPAT Phytochemical information: 
2-amino-3-(4-chloro-1H-indol-3-yl)propanoic acid
2-amino-3-(4-chloro-1H-indol-3-yl)propanoic acid
Summary

SMILES: OC(=O)C(Cc1c[nH]c2c1c(Cl)ccc2)N
InChI: InChI=1S/C11H11ClN2O2/c12-7-2-1-3-9-10(7)6(5-14-9)4-8(13)11(15)16/h1-3,5,8,14H,4,13H2,(H,15,16)
InChIKey: NRTHKYABOMUPSC-UHFFFAOYSA-N
DeepSMILES: OC=O)CCcc[nH]cc5cCl)ccc6))))))))))N
Scaffold Graph/Node/Bond level: c1ccc2[nH]ccc2c1
Scaffold Graph/Node level: C1CCC2NCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CC(=O)O; c[nH]c; cCl; CN
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: Amino acids and Peptides
NP Classifier Superclass: Small peptides
NP Classifier Class: Aminoacids
Synonymous chemical names:
(s)-4-chlorotryptophan
External chemical identifiers:
CID:CID_14048817; ChEBI:CHEBI:170088; SureChEMBL:SCHEMBL9011531
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-amino-3-(4-chloro-1H-indol-3-yl)propanoic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 238.67
Log P RDKit 1.78
Topological polar surface area (Å2) RDKit 79.11
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.09
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
2-amino-3-(4-chloro-1H-indol-3-yl)propanoic acid
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.762638
2-amino-3-(4-chloro-1H-indol-3-yl)propanoic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.14
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No