US9394285, 10

ID: ALA3983520

PubChem CID: 86698591

Max Phase: Preclinical

Molecular Formula: C19H17ClN2O4

Molecular Weight: 372.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NCCOc1ccc(-c2cc3c(C(=O)O)c[nH]c3cc2Cl)cc1

Standard InChI:  InChI=1S/C19H17ClN2O4/c1-11(23)21-6-7-26-13-4-2-12(3-5-13)14-8-15-16(19(24)25)10-22-18(15)9-17(14)20/h2-5,8-10,22H,6-7H2,1H3,(H,21,23)(H,24,25)

Standard InChI Key:  NWINTRMXZDHKDU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   10.1178   -7.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0765   -8.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0729   -9.4716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7795   -7.5165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7840   -6.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4870   -5.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -3.7597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -3.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115    2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8032    3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133    1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6890    4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    5.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8631    3.8342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 16  2  0
 20 21  1  0
 21 22  2  0
 22 14  1  0
 22 23  1  0
 17 24  1  0
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3983520

   5-{4-[2-(acetylamino)ethoxy]phenyl}-6-chloro-1H-indole-3-carboxylic acid

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: 372.81

Molecular Weight (Monoisotopic): 372.0877

AlogP: 3.70

#Rotatable Bonds: 6

Polar Surface Area: 91.42

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.52

CX Basic pKa: ┄

CX LogP: 2.85

CX LogD: -0.52

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: -0.59

References

1.  (2016)  Indole and indazole compounds that activate AMPK, 

Source

Source(1):

• BindingDB Database