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

ID: ALA1683164

PubChem CID: 53320184

Max Phase: Preclinical

Molecular Formula: C22H19BrN6O3S

Molecular Weight: 527.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(Cc2ccc(Nc3nc(N)nc(OCc4cc(Br)cs4)c3[N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C22H19BrN6O3S/c23-15-10-18(33-12-15)11-32-21-19(29(30)31)20(27-22(25)28-21)26-17-7-3-14(4-8-17)9-13-1-5-16(24)6-2-13/h1-8,10,12H,9,11,24H2,(H3,25,26,27,28)

Standard InChI Key:  XSRYUJNXUWEJQU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    8.5777   -0.9208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5766   -1.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2914   -2.1610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0078   -1.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0050   -0.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2896   -0.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8618   -2.1601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7230   -2.1591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7200   -0.5006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7169    0.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4361   -0.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2871    0.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0004    0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9979    1.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6673    2.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4100    2.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5850    2.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3325    2.0387    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.8929    3.4954    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.7242   -2.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0091   -3.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0100   -4.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7257   -4.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4419   -4.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4374   -3.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7281   -5.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4438   -5.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4413   -6.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1561   -7.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8704   -6.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8653   -5.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1499   -5.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5866   -7.0980    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:

   

   ALA1683164

   4-N-[4-[(4-aminophenyl)methyl]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: 527.40

Molecular Weight (Monoisotopic): 526.0423

AlogP: 5.29

#Rotatable Bonds: 8

Polar Surface Area: 142.22

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.98

CX Basic pKa: 4.59

CX LogP: 7.28

CX LogD: 7.28

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.16

Np Likeness Score: -1.25

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