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

ID: ALA1683166

PubChem CID: 53326715

Max Phase: Preclinical

Molecular Formula: C21H17BrN6O4S

Molecular Weight: 529.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(Oc2ccc(Nc3nc(N)nc(OCc4cc(Br)cs4)c3[N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C21H17BrN6O4S/c22-12-9-17(33-11-12)10-31-20-18(28(29)30)19(26-21(24)27-20)25-14-3-7-16(8-4-14)32-15-5-1-13(23)2-6-15/h1-9,11H,10,23H2,(H3,24,25,26,27)

Standard InChI Key:  WHWYGHCFNZDLJF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.8319   -9.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307  -10.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456  -10.4652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620  -10.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2591   -9.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -8.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1159  -10.4643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771  -10.4632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9742   -8.8048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9711   -7.9798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6902   -9.2146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5413   -7.9872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2545   -7.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2521   -6.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215   -6.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642   -5.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391   -5.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5867   -6.2655    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1471   -4.8087    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.9784  -11.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2633  -11.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642  -12.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9799  -12.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6961  -12.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6916  -11.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9823  -13.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6979  -14.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954  -14.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4103  -15.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1245  -14.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1195  -14.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4041  -13.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8407  -15.4021    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:

   

   ALA1683166

   4-N-[4-(4-aminophenoxy)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: 529.38

Molecular Weight (Monoisotopic): 528.0215

AlogP: 5.49

#Rotatable Bonds: 8

Polar Surface Area: 151.45

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.24

CX Basic pKa: 4.46

CX LogP: 6.69

CX LogD: 6.69

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.15

Np Likeness Score: -1.32

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