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

ID: ALA1683168

PubChem CID: 53324160

Max Phase: Preclinical

Molecular Formula: C24H22N6O3

Molecular Weight: 442.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(Cc2ccc(Nc3nc(N)nc(OCc4ccccc4)c3[N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C24H22N6O3/c25-19-10-6-16(7-11-19)14-17-8-12-20(13-9-17)27-22-21(30(31)32)23(29-24(26)28-22)33-15-18-4-2-1-3-5-18/h1-13H,14-15,25H2,(H3,26,27,28,29)

Standard InChI Key:  DCHXFIWIXOKSMG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.4736   -9.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4724   -9.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1872  -10.3402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9037   -9.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9008   -9.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1854   -8.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7576  -10.3393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6188  -10.3382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6159   -8.6798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6128   -7.8548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3319   -9.0896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1830   -7.8622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8962   -7.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8937   -6.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6201  -11.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9049  -11.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9059  -12.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6215  -12.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3377  -12.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3333  -11.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6239  -13.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3396  -14.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3371  -14.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0519  -15.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7662  -14.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7611  -14.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0457  -13.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4824  -15.2771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6088   -6.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6067   -5.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8905   -4.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1749   -5.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1805   -6.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  8  1  0
 16 17  1  0
 17 18  2  0
  4  5  1  0
 18 19  1  0
  2  3  1  0
 19 20  2  0
 20 15  1  0
  9 10  2  0
 18 21  1  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
  6  1  1  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
 27 22  1  0
  1  2  2  0
 25 28  1  0
 13 14  1  0
 14 29  2  0
  2  7  1  0
 29 30  1  0
  8 15  1  0
 30 31  2  0
  3  4  2  0
 31 32  1  0
 15 16  2  0
 32 33  2  0
 33 14  1  0
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1683168

   4-N-[4-[(4-aminophenyl)methyl]phenyl]-5-nitro-6-phenylmethoxypyrimidine-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: 442.48

Molecular Weight (Monoisotopic): 442.1753

AlogP: 4.46

#Rotatable Bonds: 8

Polar Surface Area: 142.22

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.99

CX Basic pKa: 4.60

CX LogP: 6.60

CX LogD: 6.60

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.21

Np Likeness Score: -0.86

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