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

ID: ALA4074077

PubChem CID: 137641160

Max Phase: Preclinical

Molecular Formula: C27H25N7O6S

Molecular Weight: 575.61

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H25N7O6S/c1-4-25(35)29-18-6-5-7-19(14-18)30-26-23(34(36)37)16-28-27(32-26)31-20-10-13-22(24(15-20)40-3)33-41(38,39)21-11-8-17(2)9-12-21/h4-16,33H,1H2,2-3H3,(H,29,35)(H2,28,30,31,32)

Standard InChI Key:  AAILMKXKVXJRLD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 41 44  0  0  0  0  0  0  0  0999 V2000
    2.5589  -16.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3761  -16.5296    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9675  -15.8218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7944  -11.6264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7933  -12.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5013  -12.8549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2110  -12.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2082  -11.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4995  -11.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9193  -12.8529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9206  -13.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0852  -12.8539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0846  -13.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3765  -14.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755  -14.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7913  -14.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2122  -14.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2132  -14.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9221  -15.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6315  -14.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6270  -14.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3412  -15.2939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3454  -16.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0552  -16.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6398  -16.5232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0594  -17.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0838  -16.1212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3768  -17.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6672  -17.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673  -18.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757  -18.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0856  -18.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0820  -17.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9165  -11.2102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9134  -10.3930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6257  -11.6161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026  -15.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5048  -16.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3773  -19.7962    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
 39 40  1  0
 33 41  1  0
M  CHG  2  36   1  38  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4074077

   ---

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: 575.61

Molecular Weight (Monoisotopic): 575.1587

AlogP: 5.11

#Rotatable Bonds: 11

Polar Surface Area: 177.48

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.49

CX Basic pKa: 1.82

CX LogP: 6.28

CX LogD: 6.06

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.11

Np Likeness Score: -1.67

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