US9394285, 68

ID: ALA3979636

PubChem CID: 86698728

Max Phase: Preclinical

Molecular Formula: C21H14BrNO3

Molecular Weight: 408.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1c[nH]c2cc(Br)c(-c3ccc(-c4ccccc4O)cc3)cc12

Standard InChI:  InChI=1S/C21H14BrNO3/c22-18-10-19-16(17(11-23-19)21(25)26)9-15(18)13-7-5-12(6-8-13)14-3-1-2-4-20(14)24/h1-11,23-24H,(H,25,26)

Standard InChI Key:  JWSCPUAEMWNWNC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -1.8631   -3.8341    0.0000 O   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
    0.3114   -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 Br  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
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5002    3.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7969    2.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0983    3.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1031    5.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8065    5.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5050    5.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4677    5.8480    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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13  4  1  0
 13  7  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3979636

   6-Bromo-5-(2'-hydroxybiphenyl-4-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: 408.25

Molecular Weight (Monoisotopic): 407.0157

AlogP: 5.67

#Rotatable Bonds: 3

Polar Surface Area: 73.32

Molecular Species: ACID

HBA: 2

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.52

CX Basic pKa: ┄

CX LogP: 5.49

CX LogD: 2.12

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: 0.18

References

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

Source

Source(1):

• BindingDB Database