US9394285, 126

ID: ALA3979205

Max Phase: Preclinical

Molecular Formula: C18H15ClN2O3

Molecular Weight: 342.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1n[nH]c2cc(Cl)c(-c3ccc([C@H]4C[C@H](O)C4)cc3)cc12

Standard InChI:  InChI=1S/C18H15ClN2O3/c19-15-8-16-14(17(18(23)24)21-20-16)7-13(15)10-3-1-9(2-4-10)11-5-12(22)6-11/h1-4,7-8,11-12,22H,5-6H2,(H,20,21)(H,23,24)/t11-,12-

Standard InChI Key:  AAORADYAVNVBAV-HAQNSBGRSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  1  0  0  0  0  0999 V2000
    9.3194   -5.4008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2821   -4.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8985   -3.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4930   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8320   -5.1811    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
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  2  1  0
  4  6  1  6
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 14  2  0
 18 19  1  0
 19 20  2  0
 20 12  1  0
 20 21  1  0
 15 22  1  0
 22 23  2  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3979205

   ---

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: 342.78

Molecular Weight (Monoisotopic): 342.0771

AlogP: 3.82

#Rotatable Bonds: 3

Polar Surface Area: 86.21

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.12

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: -0.03

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.68

Np Likeness Score: -0.22

References

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

Source

Source(1):

• BindingDB Database