5-Bromo-4-(2-fluoro-4-nitrophenoxy)-N-(3,4,5-trimethoxyphenyl)pyrimidin-2-amine

ID: ALA4758675

PubChem CID: 162658365

Max Phase: Preclinical

Molecular Formula: C19H16BrFN4O6

Molecular Weight: 495.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(Nc2ncc(Br)c(Oc3ccc([N+](=O)[O-])cc3F)n2)cc(OC)c1OC

Standard InChI:  InChI=1S/C19H16BrFN4O6/c1-28-15-6-10(7-16(29-2)17(15)30-3)23-19-22-9-12(20)18(24-19)31-14-5-4-11(25(26)27)8-13(14)21/h4-9H,1-3H3,(H,22,23,24)

Standard InChI Key:  CVOMZGNACQPPDA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   31.2470   -2.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2459   -3.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9606   -3.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9588   -1.8412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6741   -2.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6729   -3.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3898   -3.4986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3922   -1.8326    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   34.1137   -2.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1124   -3.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8284   -3.4951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5463   -3.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5435   -2.2491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8269   -1.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2612   -3.4926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9751   -3.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6886   -3.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4019   -3.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4012   -2.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6813   -1.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9708   -2.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9603   -4.3192    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.5341   -1.8459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8197   -2.2586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5339   -1.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1146   -1.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8301   -2.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1168   -3.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1176   -4.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6771   -1.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3895   -0.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  3 22  1  0
 23 24  2  0
 23 25  1  0
  1 23  1  0
 19 26  1  0
 26 27  1  0
 18 28  1  0
 28 29  1  0
 20 30  1  0
 30 31  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4758675

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 495.26

Molecular Weight (Monoisotopic): 494.0237

AlogP: 4.85

#Rotatable Bonds: 8

Polar Surface Area: 117.87

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.99

CX Basic pKa: 1.40

CX LogP: 4.64

CX LogD: 4.64

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -1.33

References

1. Sun D,Yang Z,Zhen Y,Yang Y,Chen Y,Yuan Y,Zhang L,Zeng X,Chen L.  (2020)  Discovery of 5-bromo-4-phenoxy-N-phenylpyrimidin-2-amine derivatives as novel ULK1 inhibitors that block autophagy and induce apoptosis in non-small cell lung cancer.,  208  [PMID:32961380] [10.1016/j.ejmech.2020.112782]

Source

Source(1):

• Scientific Literature