1-(2-(4-chlorophenoxy)acetyl)-N-methylindoline-2-carboxamide

ID: ALA3623005

Cas Number: 1100789-67-0

PubChem CID: 18587974

Max Phase: Preclinical

Molecular Formula: C18H17ClN2O3

Molecular Weight: 344.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)C1Cc2ccccc2N1C(=O)COc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C18H17ClN2O3/c1-20-18(23)16-10-12-4-2-3-5-15(12)21(16)17(22)11-24-14-8-6-13(19)7-9-14/h2-9,16H,10-11H2,1H3,(H,20,23)

Standard InChI Key:  WORZSRYKTGYIKJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7008   -0.9930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208    1.3475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877   -3.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -4.3539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5974   -4.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0717   -6.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5412   -6.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5365   -5.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0623   -3.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5928   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0207    1.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7121   -5.5003    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  7 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 12 23  1  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3623005

   1-(2-(4-chlorophenoxy)acetyl)-N-methylindoline-2-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 344.80

Molecular Weight (Monoisotopic): 344.0928

AlogP: 2.42

#Rotatable Bonds: 4

Polar Surface Area: 58.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.58

CX Basic pKa: ┄

CX LogP: 2.34

CX LogD: 2.34

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.93

Np Likeness Score: -1.40

References

1. Cleghorn LA, Albrecht S, Stojanovski L, Simeons FR, Norval S, Kime R, Collie IT, De Rycker M, Campbell L, Hallyburton I, Frearson JA, Wyatt PG, Read KD, Gilbert IH..  (2015)  Discovery of Indoline-2-carboxamide Derivatives as a New Class of Brain-Penetrant Inhibitors of Trypanosoma brucei.,  58  (19): [PMID:26418485] [10.1021/acs.jmedchem.5b00596]

2. Izquierdo, M; Lin, D; De Rycker, M.  (2023)  RapidFire TcLAP Compounds Screening,  [10.6019/CHEMBL5305021]

Source

Source(2):

• Scientific Literature
• University of Dundee - T. cruzi data