3-(3-bromo-4-methoxybenzyl)-5-(3,5-dibromo-4-(3-morpholinopropoxy)phenyl)pyrazin-2(1H)-one

ID: ALA2417881

PubChem CID: 72163729

Max Phase: Preclinical

Molecular Formula: C25H26Br3N3O4

Molecular Weight: 672.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2nc(-c3cc(Br)c(OCCCN4CCOCC4)c(Br)c3)c[nH]c2=O)cc1Br

Standard InChI:  InChI=1S/C25H26Br3N3O4/c1-33-23-4-3-16(11-18(23)26)12-21-25(32)29-15-22(30-21)17-13-19(27)24(20(28)14-17)35-8-2-5-31-6-9-34-10-7-31/h3-4,11,13-15H,2,5-10,12H2,1H3,(H,29,32)

Standard InChI Key:  SQJVJCSXGWSIER-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.3571  -14.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3571  -15.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0624  -15.4111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7677  -15.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7677  -14.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0624  -13.7767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4730  -13.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1798  -14.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8882  -13.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8910  -12.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1795  -12.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4740  -12.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6482  -13.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6458  -12.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3557  -12.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3537  -11.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6442  -11.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9354  -11.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9409  -12.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500  -15.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1790  -11.7457    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.5945  -14.2025    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.5994  -12.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3064  -12.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0148  -12.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7218  -12.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4302  -12.5705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1373  -12.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4315  -11.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1399  -11.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8456  -12.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8469  -11.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0604  -11.3279    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.6408  -10.5137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3467  -10.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
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  5  7  1  0
  1 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
  2 20  2  0
 11 21  1  0
  9 22  1  0
 10 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 32  1  0
 28 31  1  0
 31 32  1  0
 16 33  1  0
 17 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417881

   3-[(3-bromo-4-methoxyphenyl)methyl]-5-[3,5-dibromo-4-(3-morpholin-4-ylpropoxy)phenyl]-1H-pyrazin-2-one

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: 672.21

Molecular Weight (Monoisotopic): 668.9473

AlogP: 5.42

#Rotatable Bonds: 9

Polar Surface Area: 76.68

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.81

CX Basic pKa: 6.87

CX LogP: 4.66

CX LogD: 4.54

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.31

Np Likeness Score: -0.72

References

1. Saha S, Reddy ChV, Xu S, Sankar S, Neamati N, Patro B..  (2013)  Synthesis and SAR studies of marine natural products ma'edamines A, B and their analogues.,  23  (18): [PMID:23927972] [10.1016/j.bmcl.2013.07.017]

Source

Source(1):

• Scientific Literature