US9394285, 143

ID: ALA3984291

PubChem CID: 89837154

Max Phase: Preclinical

Molecular Formula: C20H18FNO3

Molecular Weight: 339.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1c[nH]c2cc(F)c(-c3ccc(C4(CO)CCC4)cc3)cc12

Standard InChI:  InChI=1S/C20H18FNO3/c21-17-9-18-15(16(10-22-18)19(24)25)8-14(17)12-2-4-13(5-3-12)20(11-23)6-1-7-20/h2-5,8-10,22-23H,1,6-7,11H2,(H,24,25)

Standard InChI Key:  ZGFPYTOFALGVHM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    7.5244   -5.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4874   -5.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4921   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8039   -2.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2515   -2.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8586   -4.1990    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 F   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  1  0
  4  5  1  0
  5  6  1  0
  6  3  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 10 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:

   

   ALA3984291

   6-fluoro-5-[4-[1-(hydroxymethyl)cyclobutyl]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: 339.37

Molecular Weight (Monoisotopic): 339.1271

AlogP: 4.09

#Rotatable Bonds: 4

Polar Surface Area: 73.32

Molecular Species: ACID

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.52

CX Basic pKa: ┄

CX LogP: 3.76

CX LogD: 0.40

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: 0.17

References

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

Source

Source(1):

• BindingDB Database