US9394303, 61

ID: ALA3908553

PubChem CID: 129012571

Max Phase: Preclinical

Molecular Formula: C25H19N3O3S

Molecular Weight: 441.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(Cc2ccc(Oc3ccccc3)cc2)c2nc(-c3cccs3)cc(C(=O)O)c12

Standard InChI:  InChI=1S/C25H19N3O3S/c1-16-23-20(25(29)30)14-21(22-8-5-13-32-22)26-24(23)28(27-16)15-17-9-11-19(12-10-17)31-18-6-3-2-4-7-18/h2-14H,15H2,1H3,(H,29,30)

Standard InChI Key:  AOKJSDQDESVTNU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -0.4916   -3.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.2121    3.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    5.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537    5.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149    3.8587    0.0000 S   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
 13 14  2  0
 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  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3908553

   ---

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: 441.51

Molecular Weight (Monoisotopic): 441.1147

AlogP: 6.01

#Rotatable Bonds: 6

Polar Surface Area: 77.24

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.52

CX Basic pKa: 1.81

CX LogP: 5.25

CX LogD: 2.02

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.35

Np Likeness Score: -1.72

References

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

Source

Source(1):

• BindingDB Database