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

ID: ALA1683170

PubChem CID: 53317587

Max Phase: Preclinical

Molecular Formula: C23H20N6O4

Molecular Weight: 444.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(Oc2ccc(Nc3nc(N)nc(OCc4ccccc4)c3[N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C23H20N6O4/c24-16-6-10-18(11-7-16)33-19-12-8-17(9-13-19)26-21-20(29(30)31)22(28-23(25)27-21)32-14-15-4-2-1-3-5-15/h1-13H,14,24H2,(H3,25,26,27,28)

Standard InChI Key:  FVZNMXVMBVYCQN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.8861  -20.0416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8849  -20.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5997  -21.2819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3162  -20.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3133  -20.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979  -19.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1701  -21.2809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0313  -21.2799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284  -19.6214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0253  -18.7964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7444  -20.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955  -18.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087  -18.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3062  -17.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0326  -22.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3174  -22.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3184  -23.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340  -23.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7502  -23.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7458  -22.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0364  -24.5784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521  -24.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7496  -25.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4644  -26.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1787  -25.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1736  -24.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582  -24.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8949  -26.2188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0213  -17.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192  -16.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3030  -15.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5874  -16.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5930  -17.1606    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:

   

   ALA1683170

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

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: 444.45

Molecular Weight (Monoisotopic): 444.1546

AlogP: 4.66

#Rotatable Bonds: 8

Polar Surface Area: 151.45

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.24

CX Basic pKa: 4.46

CX LogP: 6.01

CX LogD: 6.01

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.20

Np Likeness Score: -0.94

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