US9394285, 188

ID: ALA3983491

PubChem CID: 90421956

Max Phase: Preclinical

Molecular Formula: C23H24ClN3O4

Molecular Weight: 441.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(CCCOc2ccc(-c3cc4c(C(=O)O)c[nH]c4cc3Cl)cc2)CC1=O

Standard InChI:  InChI=1S/C23H24ClN3O4/c1-26-8-9-27(14-22(26)28)7-2-10-31-16-5-3-15(4-6-16)17-11-18-19(23(29)30)13-25-21(18)12-20(17)24/h3-6,11-13,25H,2,7-10,14H2,1H3,(H,29,30)

Standard InChI Key:  VIXDPCATZMZUQX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   12.7105  -10.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6723   -9.7758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3720  -10.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0742   -9.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0765   -8.2716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7795   -7.5165    0.0000 C   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
   10.3769   -7.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6747   -8.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7149   -7.6775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 18  2  0
 22 23  1  0
 23 24  2  0
 24 16  1  0
 24 25  1  0
 19 26  1  0
 26 27  2  0
 26 28  1  0
  5 29  1  0
 29 30  1  0
 30  2  1  0
 30 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3983491

   6-chloro-5-[4-[3-(4-methyl-3-oxopiperazin-1-yl)propoxy]phenyl]-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: 441.92

Molecular Weight (Monoisotopic): 441.1455

AlogP: 3.73

#Rotatable Bonds: 7

Polar Surface Area: 85.87

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.52

CX Basic pKa: 6.48

CX LogP: 0.29

CX LogD: -0.39

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.55

Np Likeness Score: -0.75

References

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

Source

Source(1):

• BindingDB Database