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

ID: ALA2417886

PubChem CID: 72163846

Max Phase: Preclinical

Molecular Formula: C26H28Br3N3O4

Molecular Weight: 686.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2nc(-c3cc(Br)c(OCCCCN4CCOCC4)c(Br)c3)c[nH]c2=O)cc1Br

Standard InChI:  InChI=1S/C26H28Br3N3O4/c1-34-24-5-4-17(12-19(24)27)13-22-26(33)30-16-23(31-22)18-14-20(28)25(21(29)15-18)36-9-3-2-6-32-7-10-35-11-8-32/h4-5,12,14-16H,2-3,6-11,13H2,1H3,(H,30,33)

Standard InChI Key:  BFZIYAZYUKUKHG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   11.4159  -25.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4159  -26.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1212  -27.0127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8265  -26.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8265  -25.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1212  -25.3783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5317  -25.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2385  -25.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9469  -25.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9498  -24.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2383  -24.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5328  -24.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7070  -25.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7046  -24.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4145  -24.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4124  -23.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7030  -22.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9942  -23.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9997  -24.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7088  -27.0179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2378  -23.3474    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.6533  -25.8041    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.6581  -24.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3652  -24.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0736  -24.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7806  -24.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4890  -24.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1960  -24.5819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1924  -25.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8954  -25.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6062  -25.4056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6095  -24.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9020  -24.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1192  -22.9295    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.6995  -22.1153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4055  -21.7037    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
 12  7  1  0
  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
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 16 34  1  0
 17 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417886

   3-[(3-bromo-4-methoxyphenyl)methyl]-5-[3,5-dibromo-4-(4-morpholin-4-ylbutoxy)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: 686.24

Molecular Weight (Monoisotopic): 682.9630

AlogP: 5.82

#Rotatable Bonds: 10

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: 7.49

CX LogP: 5.17

CX LogD: 4.82

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.27

Np Likeness Score: -0.67

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