US9394285, 16

ID: ALA3980024

PubChem CID: 86698611

Max Phase: Preclinical

Molecular Formula: C20H19ClN2O4S

Molecular Weight: 418.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)N1CCC(c2ccc(-c3cc4c(C(=O)O)c[nH]c4cc3Cl)cc2)C1

Standard InChI:  InChI=1S/C20H19ClN2O4S/c1-28(26,27)23-7-6-14(11-23)12-2-4-13(5-3-12)15-8-16-17(20(24)25)10-22-19(16)9-18(15)21/h2-5,8-10,14,22H,6-7,11H2,1H3,(H,24,25)

Standard InChI Key:  SKNDTMSDOZFWLP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    7.9888   -7.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6975   -6.9254    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8904   -7.0554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1816   -8.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0924   -5.5548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8466   -4.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8464   -3.1402    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
    6.6262   -5.2383    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 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  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 18  2  0
 22 23  1  0
 23 24  2  0
 24 16  1  0
 24 25  1  0
 19 26  1  0
 26 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980024

   6-chloro-5-{4-[1-(methylsulfonyl)pyrrolidin-3-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: 418.90

Molecular Weight (Monoisotopic): 418.0754

AlogP: 3.94

#Rotatable Bonds: 4

Polar Surface Area: 90.47

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.52

CX Basic pKa: ┄

CX LogP: 2.82

CX LogD: -0.55

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -0.91

References

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

Source

Source(1):

• BindingDB Database