US9394285, 148

ID: ALA3980011

PubChem CID: 89837077

Max Phase: Preclinical

Molecular Formula: C19H18ClNO4

Molecular Weight: 359.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(CO)c1ccc(-c2cc3c(C(=O)O)c[nH]c3cc2Cl)cc1O

Standard InChI:  InChI=1S/C19H18ClNO4/c1-19(2,9-22)14-4-3-10(5-17(14)23)11-6-12-13(18(24)25)8-21-16(12)7-15(11)20/h3-8,21-23H,9H2,1-2H3,(H,24,25)

Standard InChI Key:  ZGFPHNJLXVUBPK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    7.5331   -3.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4931   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5317   -4.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5299   -5.8595    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
    3.8924   -4.9525    0.0000 O   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
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 11 12  1  0
  9 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 15  2  0
 19 20  1  0
 20 21  2  0
 21 13  1  0
 21 22  1  0
 16 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980011

   6-chloro-5-[3-hydroxy-4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-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: 359.81

Molecular Weight (Monoisotopic): 359.0924

AlogP: 4.16

#Rotatable Bonds: 4

Polar Surface Area: 93.55

Molecular Species: ACID

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.52

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 0.57

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: 0.18

References

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

Source

Source(1):

• BindingDB Database