US9394303, 14

ID: ALA3926939

PubChem CID: 118414922

Max Phase: Preclinical

Molecular Formula: C22H19N3O3

Molecular Weight: 373.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C(=O)O)c2c(C)nn(Cc3ccc(Oc4ccccc4)cc3)c2n1

Standard InChI:  InChI=1S/C22H19N3O3/c1-14-12-19(22(26)27)20-15(2)24-25(21(20)23-14)13-16-8-10-18(11-9-16)28-17-6-4-3-5-7-17/h3-12H,13H2,1-2H3,(H,26,27)

Standard InChI Key:  MYMWHEACODUIMJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    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
    0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432    3.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0351    3.6026    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
   -2.7248    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0955    2.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -1.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -2.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6588   -2.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1271   -4.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5954   -4.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5954   -3.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0651   -3.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0641   -2.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5334   -3.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5296   -1.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0565   -0.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5872   -0.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5910   -1.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1272   -2.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6590   -1.8298    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 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  4  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 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  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 17 25  1  0
 25 26  2  0
 26 14  1  0
 12 27  1  0
 27  8  1  0
 27 28  2  0
 28  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3926939

   3,6-Dimethyl-1-[(4-phenoxyphenyl)methyl]pyrazolo[3,4-b]pyridine-4-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: 373.41

Molecular Weight (Monoisotopic): 373.1426

AlogP: 4.59

#Rotatable Bonds: 5

Polar Surface Area: 77.24

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.53

CX Basic pKa: 1.93

CX LogP: 3.56

CX LogD: 0.34

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: -1.38

References

1.  (2016)  Small molecule inhibitors of MCL-1 and uses thereof, 

Source

Source(1):

• BindingDB Database