US9394285, 32

ID: ALA3978549

PubChem CID: 86698655

Max Phase: Preclinical

Molecular Formula: C17H12N2O3

Molecular Weight: 292.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc3c(C(=O)O)c[nH]c3cc2C#N)cc1

Standard InChI:  InChI=1S/C17H12N2O3/c1-22-12-4-2-10(3-5-12)13-7-14-15(17(20)21)9-19-16(14)6-11(13)8-18/h2-7,9,19H,1H3,(H,20,21)

Standard InChI Key:  GXJZLDUBLIAVEQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    6.4879   -4.9597    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   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.2008    0.0000 N   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  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
  6  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
 18 19  3  0
 12 20  1  0
 20 21  2  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3978549

   6-Cyano-5-(4-methoxyphenyl)-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: 292.29

Molecular Weight (Monoisotopic): 292.0848

AlogP: 3.41

#Rotatable Bonds: 3

Polar Surface Area: 86.11

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.52

CX Basic pKa: ┄

CX LogP: 3.08

CX LogD: -0.29

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.77

Np Likeness Score: -0.33

References

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

Source

Source(1):

• BindingDB Database