US9394285, 107

ID: ALA3983545

PubChem CID: 86698805

Max Phase: Preclinical

Molecular Formula: C20H19ClN4O3

Molecular Weight: 398.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCN(c2ccc(-c3cc4c(C(=O)O)n[nH]c4cc3Cl)cc2)CC1

Standard InChI:  InChI=1S/C20H19ClN4O3/c1-12(26)24-6-8-25(9-7-24)14-4-2-13(3-5-14)15-10-16-18(11-17(15)21)22-23-19(16)20(27)28/h2-5,10-11H,6-9H2,1H3,(H,22,23)(H,27,28)

Standard InChI Key:  SMOBMRZREKQDOM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   11.4244   -5.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3822   -6.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3767   -7.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0864   -5.2653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0912   -3.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7945   -3.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4930   -3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4884   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7850   -6.0111    0.0000 C   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 N   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  1  0
  9  4  1  0
  7 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
M  END

Alternative Forms

1. Parent:

   

   ALA3983545

   5-(4-(4-Acetylpiperazin-1-yl)phenyl)-6-chloro-1H-indazole-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: 398.85

Molecular Weight (Monoisotopic): 398.1146

AlogP: 3.25

#Rotatable Bonds: 3

Polar Surface Area: 89.53

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.37

CX Basic pKa: 2.76

CX LogP: 2.22

CX LogD: -0.69

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -1.28

References

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

Source

Source(1):

• BindingDB Database