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

ID: ALA4094611

PubChem CID: 137655908

Max Phase: Preclinical

Molecular Formula: C27H25N7O5S

Molecular Weight: 559.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(Nc2nc(Nc3ccc(NS(=O)(=O)c4ccc(C)cc4)c(C)c3)ncc2[N+](=O)[O-])c1

Standard InChI:  InChI=1S/C27H25N7O5S/c1-4-25(35)29-19-6-5-7-20(15-19)30-26-24(34(36)37)16-28-27(32-26)31-21-10-13-23(18(3)14-21)33-40(38,39)22-11-8-17(2)9-12-22/h4-16,33H,1H2,2-3H3,(H,29,35)(H2,28,30,31,32)

Standard InChI Key:  WEOSNZZPTRHAKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 40 43  0  0  0  0  0  0  0  0999 V2000
   32.1429   -6.1991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9600   -6.1991    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.5515   -5.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3784   -1.2959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3773   -2.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0853   -2.5244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7950   -2.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7921   -1.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0835   -0.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5033   -2.5225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5046   -3.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6692   -2.5235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6686   -3.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9604   -3.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9594   -4.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6674   -4.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3777   -4.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3752   -3.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7962   -3.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7972   -4.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5060   -4.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2154   -4.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2110   -3.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9252   -4.9634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9294   -5.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6392   -6.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2238   -6.1928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6433   -7.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6678   -5.7908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9607   -7.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2512   -7.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2513   -8.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9597   -8.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6695   -8.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6660   -7.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4959   -0.8797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4928   -0.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2051   -1.2857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0866   -4.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9612   -9.4658    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
 36 37  2  0
 36 38  1  0
  8 36  1  0
 17 39  1  0
 33 40  1  0
M  CHG  2  36   1  38  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4094611

   ---

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: 559.61

Molecular Weight (Monoisotopic): 559.1638

AlogP: 5.41

#Rotatable Bonds: 10

Polar Surface Area: 168.25

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.47

CX Basic pKa: 1.95

CX LogP: 6.95

CX LogD: 6.92

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.11

Np Likeness Score: -1.79

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