2-(3-Acrylamido-4-methylphenylamino)-N-(5-(3,4-dimethoxybenzamido)-2-methylphenyl)-4-(methylamino)pyrimidine-5-carboxamide

ID: ALA4089476

PubChem CID: 122633242

Max Phase: Preclinical

Molecular Formula: C32H33N7O5

Molecular Weight: 595.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cc(Nc2ncc(C(=O)Nc3cc(NC(=O)c4ccc(OC)c(OC)c4)ccc3C)c(NC)n2)ccc1C

Standard InChI:  InChI=1S/C32H33N7O5/c1-7-28(40)37-24-16-22(12-9-18(24)2)36-32-34-17-23(29(33-4)39-32)31(42)38-25-15-21(11-8-19(25)3)35-30(41)20-10-13-26(43-5)27(14-20)44-6/h7-17H,1H2,2-6H3,(H,35,41)(H,37,40)(H,38,42)(H2,33,34,36,39)

Standard InChI Key:  NYCFYFJQJVVPRT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 44 47  0  0  0  0  0  0  0  0999 V2000
   33.7965  -24.1896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7953  -25.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5034  -25.4182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2130  -25.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2102  -24.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5016  -23.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9164  -23.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6256  -24.1807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9133  -22.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3318  -23.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9214  -25.4162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9227  -26.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0394  -24.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7451  -23.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7425  -22.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0283  -22.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3255  -22.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6147  -22.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0873  -25.4172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0866  -26.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3785  -26.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3775  -27.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0854  -27.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7958  -27.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7933  -26.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0859  -28.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5046  -27.8615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.4542  -24.1745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.1605  -23.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8696  -24.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1578  -22.9464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.8677  -24.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5760  -25.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2833  -24.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2780  -24.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5692  -23.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2112  -27.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9200  -27.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2090  -26.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9223  -28.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9929  -25.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.9967  -26.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9829  -23.7477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.6934  -24.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
  4 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 10  1  0
 17 18  1  0
  2 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 24 27  1  0
 14 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 30  1  0
 27 37  1  0
 37 38  1  0
 37 39  2  0
 38 40  2  0
 34 41  1  0
 41 42  1  0
 35 43  1  0
 43 44  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089476

   ---

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: 595.66

Molecular Weight (Monoisotopic): 595.2543

AlogP: 5.53

#Rotatable Bonds: 11

Polar Surface Area: 155.60

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.80

CX Basic pKa: 4.81

CX LogP: 5.77

CX LogD: 5.77

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.14

Np Likeness Score: -1.10

References

1. Liang X, Lv F, Wang B, Yu K, Wu H, Qi Z, Jiang Z, Chen C, Wang A, Miao W, Wang W, Hu Z, Liu J, Liu X, Zhao Z, Wang L, Zhang S, Ye Z, Wang C, Ren T, Wang Y, Liu Q, Liu J..  (2017)  Discovery of 2-((3-Acrylamido-4-methylphenyl)amino)-N-(2-methyl-5-(3,4,5-trimethoxybenzamido)phenyl)-4-(methylamino)pyrimidine-5-carboxamide (CHMFL-BMX-078) as a Highly Potent and Selective Type II Irreversible Bone Marrow Kinase in the X Chromosome (BMX) Kinase Inhibitor.,  60  (5): [PMID:28140585] [10.1021/acs.jmedchem.6b01413]

Source

Source(1):

• Scientific Literature