US9394285, 73

ID: ALA3978055

PubChem CID: 86698739

Max Phase: Preclinical

Molecular Formula: C15H13ClN4O2

Molecular Weight: 316.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ncc(-c2cc3c(C(=O)O)c[nH]c3cc2Cl)cn1

Standard InChI:  InChI=1S/C15H13ClN4O2/c1-20(2)15-18-5-8(6-19-15)9-3-10-11(14(21)22)7-17-13(10)4-12(9)16/h3-7,17H,1-2H3,(H,21,22)

Standard InChI Key:  LUTPDSUMKRMXBH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    6.4879   -4.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -3.7597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5328   -3.1632    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 N   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 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
   -0.3115    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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 16 17  1  0
 17 18  2  0
 18 10  1  0
 18 19  1  0
 13 20  1  0
 20 21  2  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3978055

   6-chloro-5-[2-(dimethylamino)pyrimidin-5-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: 316.75

Molecular Weight (Monoisotopic): 316.0727

AlogP: 3.04

#Rotatable Bonds: 3

Polar Surface Area: 82.11

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.59

CX Basic pKa: 2.67

CX LogP: 2.55

CX LogD: -0.52

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: -0.65

References

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

Source

Source(1):

• BindingDB Database