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

ID: ALA4071567

PubChem CID: 137639108

Max Phase: Preclinical

Molecular Formula: C26H22ClN5O5S

Molecular Weight: 552.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(Oc2nc(Nc3ccc(NS(=O)(=O)c4ccc(OC)cc4)cc3)ncc2Cl)c1

Standard InChI:  InChI=1S/C26H22ClN5O5S/c1-3-24(33)29-19-5-4-6-21(15-19)37-25-23(27)16-28-26(31-25)30-17-7-9-18(10-8-17)32-38(34,35)22-13-11-20(36-2)12-14-22/h3-16,32H,1H2,2H3,(H,29,33)(H,28,30,31)

Standard InChI Key:  JAZDXGNHKJRAMD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.4458  -27.4083    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0333  -26.6938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8778  -22.4582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8765  -23.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914  -23.6985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3078  -23.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3050  -22.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5896  -22.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0230  -23.6966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4462  -24.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4452  -25.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1599  -26.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4584  -26.1608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4627  -26.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1792  -27.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7502  -27.4019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1834  -28.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604  -26.9961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4465  -28.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7301  -28.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302  -29.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4455  -29.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621  -29.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1585  -28.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0179  -22.0395    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4470  -30.7062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7334  -31.1200    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
 37 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4071567

   ---

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: 552.01

Molecular Weight (Monoisotopic): 551.1030

AlogP: 5.60

#Rotatable Bonds: 10

Polar Surface Area: 131.54

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.51

CX Basic pKa: 1.73

CX LogP: 5.19

CX LogD: 5.16

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.22

Np Likeness Score: -1.43

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