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

ID: ALA2417887

PubChem CID: 72163847

Max Phase: Preclinical

Molecular Formula: C24H26Br3N3O3

Molecular Weight: 644.20

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H26Br3N3O3/c1-30(2)8-4-5-9-33-23-18(26)12-16(13-19(23)27)21-14-28-24(31)20(29-21)11-15-6-7-22(32-3)17(25)10-15/h6-7,10,12-14H,4-5,8-9,11H2,1-3H3,(H,28,31)

Standard InChI Key:  BNRZXMBKJQOUNE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   21.2676  -24.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2676  -25.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9729  -25.5641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6782  -25.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6782  -24.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9729  -23.9297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3834  -23.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0902  -24.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7986  -23.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8015  -23.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0900  -22.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3845  -23.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5587  -23.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5563  -23.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2662  -22.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2641  -21.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5547  -21.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8459  -21.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8514  -22.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5605  -25.5692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0895  -21.8987    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   25.5049  -24.3555    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   25.5098  -22.7189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2169  -23.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9253  -22.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6323  -23.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3407  -22.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0477  -23.1332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0441  -23.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7537  -22.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9708  -21.4809    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   20.5512  -20.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2572  -20.2551    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 30  1  0
 16 31  1  0
 17 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417887

   3-[(3-bromo-4-methoxyphenyl)methyl]-5-[3,5-dibromo-4-[4-(dimethylamino)butoxy]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: 644.20

Molecular Weight (Monoisotopic): 640.9524

AlogP: 6.04

#Rotatable Bonds: 10

Polar Surface Area: 67.45

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.85

CX Basic pKa: 9.75

CX LogP: 5.13

CX LogD: 3.04

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.27

Np Likeness Score: -0.39

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