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

ID: ALA1683169

PubChem CID: 53324161

Max Phase: Preclinical

Molecular Formula: C23H21N7O3

Molecular Weight: 443.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(Nc2ccc(Nc3nc(N)nc(OCc4ccccc4)c3[N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C23H21N7O3/c24-16-6-8-17(9-7-16)26-18-10-12-19(13-11-18)27-21-20(30(31)32)22(29-23(25)28-21)33-14-15-4-2-1-3-5-15/h1-13,26H,14,24H2,(H3,25,27,28,29)

Standard InChI Key:  FXTIOWSHKSPXSW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.6359  -20.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9211  -21.4069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2047  -20.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2075  -20.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9229  -19.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3507  -21.4059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895  -21.4049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4925  -19.7464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956  -18.9214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7764  -20.1562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9254  -18.9289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2121  -18.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4883  -22.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034  -22.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2025  -23.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7706  -23.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751  -22.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844  -24.7034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7687  -25.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7712  -25.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564  -26.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6579  -25.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6528  -25.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0626  -24.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741  -26.3438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4995  -17.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016  -16.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2179  -16.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9334  -16.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9278  -17.2856    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:

   

   ALA1683169

   4-N-[4-(4-aminoanilino)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: 443.47

Molecular Weight (Monoisotopic): 443.1706

AlogP: 4.62

#Rotatable Bonds: 8

Polar Surface Area: 154.25

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.90

CX Basic pKa: 5.36

CX LogP: 5.95

CX LogD: 5.94

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.17

Np Likeness Score: -0.89

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