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

ID: ALA4779407

PubChem CID: 162663675

Max Phase: Preclinical

Molecular Formula: C16H9Br2FN4O3

Molecular Weight: 484.08

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H9Br2FN4O3/c17-9-1-3-10(4-2-9)21-16-20-8-12(18)15(22-16)26-14-6-5-11(23(24)25)7-13(14)19/h1-8H,(H,20,21,22)

Standard InChI Key:  QARCGHJYBXBEBZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   11.2998   -8.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2986   -9.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0130   -9.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0112   -8.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7261   -8.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7249   -9.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4413   -9.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4438   -8.2358    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.1647   -8.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1635   -9.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8792   -9.8973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5965   -9.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5938   -8.6520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8775   -8.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3111   -9.8948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0246   -9.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7377   -9.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4506   -9.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4499   -8.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7304   -8.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0203   -8.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0127  -10.7210    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5850   -8.2452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8711   -8.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5848   -7.4207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1628   -8.2453    0.0000 Br  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
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4779407

   ---

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: 484.08

Molecular Weight (Monoisotopic): 481.9025

AlogP: 5.58

#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: 12.74

CX Basic pKa: 1.47

CX LogP: 5.88

CX LogD: 5.88

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.38

Np Likeness Score: -1.78

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