US9394303, 17

ID: ALA3922950

PubChem CID: 118414937

Max Phase: Preclinical

Molecular Formula: C29H21N3O3

Molecular Weight: 459.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(Cc2ccc(Oc3ccccc3)cc2)c2nc(C#Cc3ccccc3)cc(C(=O)O)c12

Standard InChI:  InChI=1S/C29H21N3O3/c1-20-27-26(29(33)34)18-23(15-12-21-8-4-2-5-9-21)30-28(27)32(31-20)19-22-13-16-25(17-14-22)35-24-10-6-3-7-11-24/h2-11,13-14,16-18H,19H2,1H3,(H,33,34)

Standard InChI Key:  VMUSMRANUHVVFA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 N   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
    3.8794   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8823   -2.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3506   -2.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3506   -3.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8824   -4.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8807   -5.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4102   -7.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4064   -8.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9332   -9.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4640  -10.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4678   -9.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9409   -7.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4142   -5.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -3.9859    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 N   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
   -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
   -2.6003   -1.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387   -0.8963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024   -2.6978    0.0000 O   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    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    6.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    6.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    8.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    9.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    8.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    6.7525    0.0000 C   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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
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 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 17  1  0
 17 18  2  0
 18  6  1  0
  4 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 23 27  2  0
 27  2  1  0
 27 19  1  0
 21 28  1  0
 28 29  3  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3922950

   3-Methyl-1-[(4-phenoxyphenyl)methyl]-6-(2-phenylethynyl)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: 459.51

Molecular Weight (Monoisotopic): 459.1583

AlogP: 5.68

#Rotatable Bonds: 5

Polar Surface Area: 77.24

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.51

CX Basic pKa: 1.84

CX LogP: 5.94

CX LogD: 2.72

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.34

Np Likeness Score: -1.11

References

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

Source

Source(1):

• BindingDB Database