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

ID: ALA4089960

PubChem CID: 137641918

Max Phase: Preclinical

Molecular Formula: C26H22FN7O5S

Molecular Weight: 563.57

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H22FN7O5S/c1-3-24(35)29-18-5-4-6-19(14-18)30-25-23(34(36)37)15-28-26(32-25)31-20-9-12-22(16(2)13-20)33-40(38,39)21-10-7-17(27)8-11-21/h3-15,33H,1H2,2H3,(H,29,35)(H2,28,30,31,32)

Standard InChI Key:  RLMZJNBURABDNG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 40 43  0  0  0  0  0  0  0  0999 V2000
   13.5002  -16.3314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -16.3314    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.9088  -15.6237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7357  -11.4283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7346  -12.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4426  -12.6568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1523  -12.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1494  -11.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4408  -11.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8606  -12.6548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8619  -13.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0265  -12.6558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0259  -13.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3177  -13.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.0247  -15.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7350  -14.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7325  -13.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1535  -13.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1545  -14.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8633  -15.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5728  -14.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5683  -13.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2825  -15.0958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2867  -15.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9965  -16.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5811  -16.3251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0006  -17.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0251  -15.9231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3181  -17.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6085  -17.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6086  -18.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3170  -18.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0269  -18.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0233  -17.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8577  -11.0120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8547  -10.1949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5670  -11.4180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4439  -15.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3185  -19.5981    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
 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
 33 40  1  0
M  CHG  2  36   1  38  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4089960

   ---

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: 563.57

Molecular Weight (Monoisotopic): 563.1387

AlogP: 5.24

#Rotatable Bonds: 10

Polar Surface Area: 168.25

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.43

CX Basic pKa: 1.95

CX LogP: 6.58

CX LogD: 6.55

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.11

Np Likeness Score: -1.92

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