5-Bromo-N-(4-chlorophenyl)-4-(2-fluoro-4-nitrophenoxy)pyrimidin-2-amine

ID: ALA4759627

PubChem CID: 162657789

Max Phase: Preclinical

Molecular Formula: C16H9BrClFN4O3

Molecular Weight: 439.63

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(Oc2nc(Nc3ccc(Cl)cc3)ncc2Br)c(F)c1

Standard InChI:  InChI=1S/C16H9BrClFN4O3/c17-12-8-20-16(21-10-3-1-9(18)2-4-10)22-15(12)26-14-6-5-11(23(24)25)7-13(14)19/h1-8H,(H,20,21,22)

Standard InChI Key:  LDLWNDJZEXLGGA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    0.9897   -8.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885   -9.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -9.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7011   -8.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4160   -8.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148   -9.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1313   -9.9387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1337   -8.2736    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.8547   -8.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535   -9.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5691   -9.9351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2865   -9.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2838   -8.6898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5675   -8.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0011   -9.9326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7146   -9.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4278   -9.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1407   -9.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1400   -8.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4203   -8.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7103   -8.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8529   -8.2831    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7026  -10.7587    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -8.2805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393   -8.6930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2786   -7.4561    0.0000 O   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
 19 22  1  0
  3 23  1  0
 24 25  2  0
 24 26  1  0
  1 24  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4759627

   ---

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: 439.63

Molecular Weight (Monoisotopic): 437.9531

AlogP: 5.48

#Rotatable Bonds: 5

Polar Surface Area: 90.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.62

CX Basic pKa: 1.44

CX LogP: 5.72

CX LogD: 5.72

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.42

Np Likeness Score: -1.92

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