2-Amino-4-(4-bromothenyloxy)-6-[N-(4-(4-aminophenylamino)anilino)]-5-nitropyrimidine

ID: ALA1683165

PubChem CID: 51351519

Max Phase: Preclinical

Molecular Formula: C21H18BrN7O3S

Molecular Weight: 528.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(Nc2ccc(Nc3nc(N)nc(OCc4cc(Br)cs4)c3[N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C21H18BrN7O3S/c22-12-9-17(33-11-12)10-32-20-18(29(30)31)19(27-21(24)28-20)26-16-7-5-15(6-8-16)25-14-3-1-13(23)2-4-14/h1-9,11,25H,10,23H2,(H3,24,26,27,28)

Standard InChI Key:  YUKYAOCOEPTCIM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -4.0984  -10.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3836  -10.6860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672  -10.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6700   -9.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3854   -9.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9520  -10.6841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9550   -9.0256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581   -8.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2389   -9.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3879   -8.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6746   -7.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771   -6.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0077   -6.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2650   -5.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0900   -5.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3425   -6.4863    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7821   -5.0296    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508  -11.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6659  -11.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650  -12.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9493  -13.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331  -12.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376  -11.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9469  -13.9825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2312  -14.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337  -15.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5189  -15.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1954  -15.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1903  -14.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5251  -13.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116  -15.6230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  1  0
  4  5  1  0
 16 19  1  0
  2  3  1  0
  8 20  1  0
  9 10  2  0
 20 21  2  0
  9 11  1  0
 21 22  1  0
  5  9  1  0
 22 23  2  0
  5  6  2  0
 23 24  1  0
  6 12  1  0
 24 25  2  0
 25 20  1  0
  6  1  1  0
 23 26  1  0
 12 13  1  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 13 14  1  0
 28 29  1  0
 14 15  2  0
 29 30  2  0
  2  7  1  0
 30 31  1  0
  3  4  2  0
 31 32  2  0
 32 27  1  0
  4  8  1  0
 30 33  1  0
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1683165

   4-N-[4-(4-aminoanilino)phenyl]-6-[(4-bromothiophen-2-yl)methoxy]-5-nitropyrimidine-2,4-diamine

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: 528.39

Molecular Weight (Monoisotopic): 527.0375

AlogP: 5.44

#Rotatable Bonds: 8

Polar Surface Area: 154.25

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.90

CX Basic pKa: 5.36

CX LogP: 6.63

CX LogD: 6.62

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.13

Np Likeness Score: -1.27

References

1. Lopez S, Margison GP, McElhinney RS, Cordeiro A, McMurry TB, Rozas I..  (2011)  Towards more specific O6-methylguanine-DNA methyltransferase (MGMT) inactivators.,  19  (5): [PMID:21320783] [10.1016/j.bmc.2011.01.038]

Source

Source(1):

• Scientific Literature