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

ID: ALA4097689

PubChem CID: 137661571

Max Phase: Preclinical

Molecular Formula: C26H23N7O6S

Molecular Weight: 561.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(Nc2nc(Nc3ccc(NS(=O)(=O)c4ccc(OC)cc4)cc3)ncc2[N+](=O)[O-])c1

Standard InChI:  InChI=1S/C26H23N7O6S/c1-3-24(34)28-19-5-4-6-20(15-19)29-25-23(33(35)36)16-27-26(31-25)30-17-7-9-18(10-8-17)32-40(37,38)22-13-11-21(39-2)12-14-22/h3-16,32H,1H2,2H3,(H,28,34)(H2,27,29,30,31)

Standard InChI Key:  OZAVAIUFXCUDIZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   30.2815  -15.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0987  -15.8403    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.6901  -15.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5170  -10.9371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5159  -11.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2239  -12.1656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9336  -11.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9307  -10.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2221  -10.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6419  -12.1637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   31.8078  -12.1647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   33.9348  -13.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   35.3541  -14.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.0638  -14.6046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0680  -15.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7778  -15.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3624  -15.8340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7820  -16.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8064  -15.4320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0994  -16.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3898  -17.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3899  -17.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0983  -18.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8082  -17.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8046  -17.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0999  -19.1070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3929  -19.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6390  -10.5209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.6360   -9.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3483  -10.9268    0.0000 O   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
 33 36  1  0
 36 37  1  0
 38 39  2  0
 38 40  1  0
  8 38  1  0
M  CHG  2  38   1  40  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4097689

   ---

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: 561.58

Molecular Weight (Monoisotopic): 561.1431

AlogP: 4.81

#Rotatable Bonds: 11

Polar Surface Area: 177.48

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.51

CX Basic pKa: 1.94

CX LogP: 5.77

CX LogD: 5.74

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.11

Np Likeness Score: -1.50

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