2-(4-Methyl-3-propionamidophenylamino)-N-(2-methyl-5-(3,4,5-trimethoxybenzamido)phenyl)-4-(methylamino)pyrimidine-5-carboxamide

ID: ALA4087478

PubChem CID: 122633880

Max Phase: Preclinical

Molecular Formula: C33H37N7O6

Molecular Weight: 627.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)Nc1cc(Nc2ncc(C(=O)Nc3cc(NC(=O)c4cc(OC)c(OC)c(OC)c4)ccc3C)c(NC)n2)ccc1C

Standard InChI:  InChI=1S/C33H37N7O6/c1-8-28(41)38-24-16-22(12-10-18(24)2)37-33-35-17-23(30(34-4)40-33)32(43)39-25-15-21(11-9-19(25)3)36-31(42)20-13-26(44-5)29(46-7)27(14-20)45-6/h9-17H,8H2,1-7H3,(H,36,42)(H,38,41)(H,39,43)(H2,34,35,37,40)

Standard InChI Key:  JJORFRRMKVGMOJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 46 49  0  0  0  0  0  0  0  0999 V2000
    1.0510  -10.5492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0499  -11.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7579  -11.7777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676  -11.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4648  -10.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7561  -10.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1709  -10.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8802  -10.5402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1678   -9.3171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5863  -10.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1759  -11.7757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1772  -12.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2940  -10.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9997  -10.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970   -9.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2828   -8.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -9.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8692   -8.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3419  -11.7767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3412  -12.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3677  -13.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750  -13.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3400  -14.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0504  -13.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479  -12.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3404  -15.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7592  -14.2210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7087  -10.5340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4151  -10.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1241  -10.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4124   -9.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1223  -11.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8305  -11.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8238  -10.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658  -13.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1746  -14.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4635  -12.9933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1768  -15.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5325  -10.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5338  -11.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2385  -10.1090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2350   -9.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8358  -12.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1307  -12.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2438  -11.7422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2484  -12.5594    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 40  2  0
 39 34  2  0
 34 30  1  0
 27 35  1  0
 35 36  1  0
 35 37  2  0
 36 38  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 33 43  1  0
 43 44  1  0
 40 45  1  0
 45 46  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087478

   ---

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: 627.70

Molecular Weight (Monoisotopic): 627.2805

AlogP: 5.76

#Rotatable Bonds: 12

Polar Surface Area: 164.83

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.78

CX Basic pKa: 4.81

CX LogP: 5.56

CX LogD: 5.56

Aromatic Rings: 4

Heavy Atoms: 46

QED Weighted: 0.13

Np Likeness Score: -1.17

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