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

ID: ALA2417776

PubChem CID: 72163592

Max Phase: Preclinical

Molecular Formula: C22H23Br2N3O2

Molecular Weight: 521.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCCOc1c(Br)cc(-c2c[nH]c(=O)c(Cc3ccccc3)n2)cc1Br

Standard InChI:  InChI=1S/C22H23Br2N3O2/c1-27(2)9-6-10-29-21-17(23)12-16(13-18(21)24)20-14-25-22(28)19(26-20)11-15-7-4-3-5-8-15/h3-5,7-8,12-14H,6,9-11H2,1-2H3,(H,25,28)

Standard InChI Key:  LUYUMRMCZSSWMT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    0.2146   -8.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2146   -9.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9199   -9.9673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252   -9.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252   -8.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9199   -8.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3304   -8.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372   -8.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7456   -8.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485   -7.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0370   -7.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315   -7.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4962   -8.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5021   -7.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132   -7.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111   -6.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005   -5.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2114   -6.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2087   -7.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980   -9.9724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0365   -6.3019    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.4520   -8.7587    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.4568   -7.1222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1639   -7.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8723   -7.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5793   -7.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2877   -7.1267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9947   -7.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2890   -6.3095    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
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417776

   3-benzyl-5-[3,5-dibromo-4-[3-(dimethylamino)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: 521.25

Molecular Weight (Monoisotopic): 519.0157

AlogP: 4.88

#Rotatable Bonds: 8

Polar Surface Area: 58.22

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.82

CX Basic pKa: 9.24

CX LogP: 4.14

CX LogD: 2.41

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -0.51

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