N-(3-(5-chloro-2-(3-methyl-4-(4-methylphenylsulfonamido)phenylamino)pyrimidin-4-yloxy)phenyl)acrylamide

ID: ALA4092347

PubChem CID: 137654673

Max Phase: Preclinical

Molecular Formula: C27H24ClN5O4S

Molecular Weight: 550.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(Oc2nc(Nc3ccc(NS(=O)(=O)c4ccc(C)cc4)c(C)c3)ncc2Cl)c1

Standard InChI:  InChI=1S/C27H24ClN5O4S/c1-4-25(34)30-19-6-5-7-21(15-19)37-26-23(28)16-29-27(32-26)31-20-10-13-24(18(3)14-20)33-38(35,36)22-11-8-17(2)9-12-22/h4-16,33H,1H2,2-3H3,(H,30,34)(H,29,31,32)

Standard InChI Key:  DVGVIEURKHLUGO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.7089  -27.2149    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3004  -26.5072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1273  -22.3118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1262  -23.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8342  -23.5403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5439  -23.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5410  -22.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8324  -21.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2522  -23.5383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7093  -24.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7083  -25.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4163  -25.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.6741  -25.9793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6783  -26.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3881  -27.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9727  -27.2086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3922  -28.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4167  -26.8066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7096  -28.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0001  -28.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0001  -29.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7086  -29.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4184  -29.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4149  -28.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2472  -21.8969    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.7101  -30.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8355  -25.9836    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
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 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
 17 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092347

   ---

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: 550.04

Molecular Weight (Monoisotopic): 549.1238

AlogP: 6.21

#Rotatable Bonds: 9

Polar Surface Area: 122.31

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.47

CX Basic pKa: 1.75

CX LogP: 6.38

CX LogD: 6.34

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.21

Np Likeness Score: -1.78

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