US9394285, 186

ID: ALA3978662

PubChem CID: 90421884

Max Phase: Preclinical

Molecular Formula: C18H18ClN3O4

Molecular Weight: 375.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nc(N(C)CCO)ccc1-c1cc2c(C(=O)O)c[nH]c2cc1Cl

Standard InChI:  InChI=1S/C18H18ClN3O4/c1-22(5-6-23)16-4-3-10(17(21-16)26-2)11-7-12-13(18(24)25)9-20-15(12)8-14(11)19/h3-4,7-9,20,23H,5-6H2,1-2H3,(H,24,25)

Standard InChI Key:  RKJSVUYUCNYCPW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.9456    1.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046    0.7483    0.0000 O   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
    5.1969   -1.5045    0.0000 N   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
    3.8943   -3.7525    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
    2.5987   -1.5004    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
    6.4915   -3.7597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5328   -3.1632    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
    7.7840   -6.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7804   -7.2156    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  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 11  2  0
 15 16  1  0
 16 17  2  0
 17  9  1  0
 17 18  1  0
 12 19  1  0
 19 20  2  0
 19 21  1  0
  5 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3978662

   6-chloro-5-[6-[2-hydroxyethyl(methyl)amino]-2-methoxypyridin-3-yl]-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: 375.81

Molecular Weight (Monoisotopic): 375.0986

AlogP: 3.02

#Rotatable Bonds: 6

Polar Surface Area: 98.68

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: 4.09

CX LogP: 2.34

CX LogD: -0.16

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: -0.73

References

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

Source

Source(1):

• BindingDB Database