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

ID: ALA2417778

PubChem CID: 72163594

Max Phase: Preclinical

Molecular Formula: C22H22Br3N3O3

Molecular Weight: 616.15

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H22Br3N3O3/c1-28(2)6-7-31-21-16(24)10-14(11-17(21)25)19-12-26-22(29)18(27-19)9-13-4-5-20(30-3)15(23)8-13/h4-5,8,10-12H,6-7,9H2,1-3H3,(H,26,29)

Standard InChI Key:  AAUORFNJZIOJEL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   15.8692   -7.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8692   -8.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5745   -8.4072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2798   -8.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2798   -7.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5745   -6.7728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9850   -6.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6918   -7.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4002   -6.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4031   -5.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6916   -5.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9861   -5.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1603   -6.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1579   -5.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8678   -5.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8657   -4.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1563   -4.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4474   -4.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4530   -5.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1621   -8.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1528   -3.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6911   -4.7418    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   20.1065   -7.1986    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   20.1114   -5.5621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8185   -5.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5268   -5.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2339   -5.9741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9423   -5.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2326   -6.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8588   -3.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5724   -4.3240    0.0000 Br  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
 17 21  1  0
 11 22  1  0
  9 23  1  0
 10 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 21 30  1  0
 16 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417778

   3-[(3-bromo-4-methoxyphenyl)methyl]-5-[3,5-dibromo-4-[2-(dimethylamino)ethoxy]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: 616.15

Molecular Weight (Monoisotopic): 612.9211

AlogP: 5.26

#Rotatable Bonds: 8

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: 10.82

CX Basic pKa: 8.63

CX LogP: 4.82

CX LogD: 3.56

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.37

Np Likeness Score: -0.43

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