2-Amino-4-(4-bromothenyloxy)-6-[N-(4,4'-aminobenzophenone)]-5-nitropyrimidine

ID: ALA1683167

PubChem CID: 53321500

Max Phase: Preclinical

Molecular Formula: C22H17BrN6O4S

Molecular Weight: 541.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(C(=O)c2ccc(Nc3nc(N)nc(OCc4cc(Br)cs4)c3[N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C22H17BrN6O4S/c23-14-9-17(34-11-14)10-33-21-18(29(31)32)20(27-22(25)28-21)26-16-7-3-13(4-8-16)19(30)12-1-5-15(24)6-2-12/h1-9,11H,10,24H2,(H3,25,26,27,28)

Standard InChI Key:  IGZYFNYVXLBLIX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    7.7569   -9.5541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7557  -10.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4706  -10.7944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1870  -10.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1841   -9.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4688   -9.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0409  -10.7934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9021  -10.7924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8992   -9.1339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8961   -8.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6152   -9.5437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4663   -8.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1795   -7.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1771   -7.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8465   -6.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5892   -5.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7641   -5.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5117   -6.5946    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0721   -5.1379    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.9034  -11.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1883  -12.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1892  -12.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9049  -13.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6211  -12.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6166  -12.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9073  -14.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6229  -14.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6204  -15.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3353  -15.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0495  -15.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0445  -14.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3291  -14.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7657  -15.7313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1940  -14.5054    0.0000 O   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
 26 34  2  0
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1683167

   [4-[[2-Amino-6-[(4-bromothiophen-2-yl)methoxy]-5-nitropyrimidin-4-yl]amino]phenyl]-(4-aminophenyl)methanone

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: 541.39

Molecular Weight (Monoisotopic): 540.0215

AlogP: 4.93

#Rotatable Bonds: 8

Polar Surface Area: 159.29

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.96

CX Basic pKa: 3.96

CX LogP: 6.65

CX LogD: 6.65

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.12

Np Likeness Score: -1.30

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