3-[4-(1H-Imidazol-1-yl)butoxy]-4-nitro-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide

ID: ALA4286253

PubChem CID: 145992224

Max Phase: Preclinical

Molecular Formula: C30H28N8O4

Molecular Weight: 564.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)c2ccc([N+](=O)[O-])c(OCCCCn3ccnc3)c2)cc1Nc1nccc(-c2cccnc2)n1

Standard InChI:  InChI=1S/C30H28N8O4/c1-21-6-8-24(18-26(21)36-30-33-12-10-25(35-30)23-5-4-11-31-19-23)34-29(39)22-7-9-27(38(40)41)28(17-22)42-16-3-2-14-37-15-13-32-20-37/h4-13,15,17-20H,2-3,14,16H2,1H3,(H,34,39)(H,33,35,36)

Standard InChI Key:  SMUIUUIKJMXBAL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.7949  -25.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863  -24.6062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0898  -27.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803  -27.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3798  -28.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879  -28.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981  -28.2796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7952  -27.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5011  -24.6002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2103  -25.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9036  -23.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6302  -27.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6329  -28.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366  -27.0394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9247  -28.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9271  -29.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366  -29.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0558  -29.8891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7607  -29.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4712  -29.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1761  -29.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8866  -29.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3394  -29.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8821  -29.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4686  -28.4669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6705  -28.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6413  -30.7222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3509  -31.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9355  -31.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
 19 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 23  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 35  1  0
 40 41  2  0
 40 42  1  0
 27 40  1  0
M  CHG  2  40   1  42  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4286253

   ---

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: 564.61

Molecular Weight (Monoisotopic): 564.2234

AlogP: 5.81

#Rotatable Bonds: 12

Polar Surface Area: 149.99

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.67

CX Basic pKa: 6.53

CX LogP: 4.86

CX LogD: 4.81

Aromatic Rings: 5

Heavy Atoms: 42

QED Weighted: 0.11

Np Likeness Score: -1.91

References

1. Sorrenti V, Pittalà V, Romeo G, Amata E, Dichiara M, Marrazzo A, Turnaturi R, Prezzavento O, Barbagallo I, Vanella L, Rescifina A, Floresta G, Tibullo D, Di Raimondo F, Intagliata S, Salerno L..  (2018)  Targeting heme Oxygenase-1 with hybrid compounds to overcome Imatinib resistance in chronic myeloid leukemia cell lines.,  158  [PMID:30261468] [10.1016/j.ejmech.2018.09.048]

Source

Source(1):

• Scientific Literature