N-(3-((5-Chloro-2-(4-(4-methylbenzenesulfonicamide)phenylamino)-4-pyrimidinyl)amino)phenyl)acrylamide

ID: ALA4103300

PubChem CID: 137657046

Max Phase: Preclinical

Molecular Formula: C26H23ClN6O3S

Molecular Weight: 535.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(Nc2nc(Nc3ccc(NS(=O)(=O)c4ccc(C)cc4)cc3)ncc2Cl)c1

Standard InChI:  InChI=1S/C26H23ClN6O3S/c1-3-24(34)29-20-5-4-6-21(15-20)30-25-23(27)16-28-26(32-25)31-18-9-11-19(12-10-18)33-37(35,36)22-13-7-17(2)8-14-22/h3-16,33H,1H2,2H3,(H,29,34)(H2,28,30,31,32)

Standard InChI Key:  JKXBBWRXKIOMIG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    2.5011   -7.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3183   -7.0039    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9097   -6.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7366   -2.1007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7355   -2.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4435   -3.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1532   -2.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1504   -2.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4418   -1.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8616   -3.3273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8628   -4.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0275   -3.3283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0268   -4.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3187   -4.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3177   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0256   -5.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7360   -5.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7335   -4.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1545   -4.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1554   -5.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8643   -5.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5737   -5.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5693   -4.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2835   -5.7682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2876   -6.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9974   -6.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5820   -6.9976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0016   -7.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260   -6.5956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -7.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6094   -8.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095   -9.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3180   -9.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0278   -9.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0242   -8.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8565   -1.6859    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3195  -10.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  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  1  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 11 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 11  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  2  0
 16 29  1  0
 29  2  1  0
  2 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
  8 36  1  0
 33 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103300

   ---

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: 535.03

Molecular Weight (Monoisotopic): 534.1241

AlogP: 5.85

#Rotatable Bonds: 9

Polar Surface Area: 125.11

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.42

CX Basic pKa: 2.92

CX LogP: 5.80

CX LogD: 5.77

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.20

Np Likeness Score: -1.54

References

1. Liu H, Qu M, Xu L, Han X, Wang C, Shu X, Yao J, Liu K, Peng J, Li Y, Ma X..  (2017)  Design and synthesis of sulfonamide-substituted diphenylpyrimidines (SFA-DPPYs) as potent Bruton's tyrosine kinase (BTK) inhibitors with improved activity toward B-cell lymphoblastic leukemia.,  135  [PMID:28432946] [10.1016/j.ejmech.2017.04.037]

Source

Source(1):

• Scientific Literature