US9394285, 75

ID: ALA3986249

PubChem CID: 71767830

Max Phase: Preclinical

Molecular Formula: C19H16ClNO3

Molecular Weight: 341.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1c[nH]c2cc(Cl)c(-c3ccc(C4(CO)CC4)cc3)cc12

Standard InChI:  InChI=1S/C19H16ClNO3/c20-16-8-17-14(15(9-21-17)18(23)24)7-13(16)11-1-3-12(4-2-11)19(10-22)5-6-19/h1-4,7-9,21-22H,5-6,10H2,(H,23,24)

Standard InChI Key:  HPSVQYWQVLFPRF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  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
    7.1307   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8765   -3.8307    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  1  0
  3  4  1  0
  4  5  1  0
  5  3  1  0
  3  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
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 14  2  0
 18 19  1  0
 19 20  2  0
 20 12  1  0
 20 21  1  0
 15 22  1  0
 22 23  2  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986249

   6-chloro-5-{4-[1-(hydroxymethyl)cyclopropyl]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: 341.79

Molecular Weight (Monoisotopic): 341.0819

AlogP: 4.21

#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: 3.78

CX LogD: 0.41

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: 0.17

References

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

Source

Source(1):

• BindingDB Database