3-benzyl-5-(3,5-dibromo-4-(3-(methylamino)propoxy)phenyl)pyrazin-2(1H)-one

ID: ALA2417777

PubChem CID: 72163593

Max Phase: Preclinical

Molecular Formula: C21H21Br2N3O2

Molecular Weight: 507.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCCCOc1c(Br)cc(-c2c[nH]c(=O)c(Cc3ccccc3)n2)cc1Br

Standard InChI:  InChI=1S/C21H21Br2N3O2/c1-24-8-5-9-28-20-16(22)11-15(12-17(20)23)19-13-25-21(27)18(26-19)10-14-6-3-2-4-7-14/h2-4,6-7,11-13,24H,5,8-10H2,1H3,(H,25,27)

Standard InChI Key:  JWGYFIBZFIPZON-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   10.3552   -8.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3552   -9.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0605  -10.1654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7658   -9.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7658   -8.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0605   -8.5310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4710   -8.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1778   -8.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8862   -8.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8891   -7.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1776   -7.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4721   -7.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6463   -8.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6439   -7.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3538   -7.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3517   -6.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6423   -6.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9335   -6.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9390   -7.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6481  -10.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1771   -6.5000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.5926   -8.9568    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.5974   -7.3203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3045   -7.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0129   -7.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7199   -7.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4283   -7.3248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1353   -7.7345    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
M  END

Alternative Forms

1. Parent:

   

   ALA2417777

   3-benzyl-5-[3,5-dibromo-4-[3-(methylamino)propoxy]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: 507.23

Molecular Weight (Monoisotopic): 505.0001

AlogP: 4.54

#Rotatable Bonds: 8

Polar Surface Area: 67.01

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.89

CX Basic pKa: 10.03

CX LogP: 3.48

CX LogD: 1.29

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -0.28

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