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

ID: ALA4086899

PubChem CID: 137643176

Max Phase: Preclinical

Molecular Formula: C26H22ClFN6O3S

Molecular Weight: 553.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(Nc2nc(Nc3ccc(NS(=O)(=O)c4ccc(F)cc4)c(C)c3)ncc2Cl)c1

Standard InChI:  InChI=1S/C26H22ClFN6O3S/c1-3-24(35)30-18-5-4-6-19(14-18)31-25-22(27)15-29-26(33-25)32-20-9-12-23(16(2)13-20)34-38(36,37)21-10-7-17(28)8-11-21/h3-15,34H,1H2,2H3,(H,30,35)(H2,29,31,32,33)

Standard InChI Key:  BFBFWHVADNJHTJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.7779   -6.8553    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.3693   -6.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1962   -1.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1951   -2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9031   -3.1806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6128   -2.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6100   -1.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9014   -1.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3212   -3.1787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   12.7783   -4.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7773   -5.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4852   -5.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.7431   -5.6196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7472   -6.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.0416   -6.8490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4612   -7.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4856   -6.4470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0691   -8.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7776   -9.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4874   -8.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4838   -8.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3161   -1.5373    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.9044   -5.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7791  -10.1220    0.0000 F   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
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 11 19  2  0
 19 20  1  0
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 21 22  1  0
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 23 11  1  0
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 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  2  0
 16 29  1  0
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  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
 17 37  1  0
 33 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4086899

   ---

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: 553.02

Molecular Weight (Monoisotopic): 552.1147

AlogP: 5.99

#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: 8.43

CX Basic pKa: 2.94

CX LogP: 5.94

CX LogD: 5.91

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.19

Np Likeness Score: -1.88

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