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

ID: ALA2417882

PubChem CID: 72163842

Max Phase: Preclinical

Molecular Formula: C25H28Br3N3O3

Molecular Weight: 658.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCCOc1c(Br)cc(-c2c[nH]c(=O)c(Cc3ccc(OC)c(Br)c3)n2)cc1Br

Standard InChI:  InChI=1S/C25H28Br3N3O3/c1-4-31(5-2)9-6-10-34-24-19(27)13-17(14-20(24)28)22-15-29-25(32)21(30-22)12-16-7-8-23(33-3)18(26)11-16/h7-8,11,13-15H,4-6,9-10,12H2,1-3H3,(H,29,32)

Standard InChI Key:  XSRAQPUQRGODCH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   13.1246  -20.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1246  -21.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8299  -21.9362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5351  -21.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5351  -20.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8299  -20.3018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2404  -20.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9472  -20.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6556  -20.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6585  -19.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9470  -19.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2415  -19.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4157  -20.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4133  -19.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1232  -19.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1211  -18.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4117  -17.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7028  -18.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7084  -19.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4175  -21.9414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9465  -18.2709    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.3619  -20.7276    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.3668  -19.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0739  -19.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7822  -19.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4893  -19.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1976  -19.0956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9047  -19.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1990  -18.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9073  -17.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6131  -19.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8278  -17.8530    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.4082  -17.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1142  -16.6272    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
 29 30  1  0
 28 31  1  0
 16 32  1  0
 17 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417882

   3-[(3-bromo-4-methoxyphenyl)methyl]-5-[3,5-dibromo-4-[3-(diethylamino)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: 658.23

Molecular Weight (Monoisotopic): 654.9681

AlogP: 6.43

#Rotatable Bonds: 11

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: 9.76

CX LogP: 5.32

CX LogD: 3.22

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.24

Np Likeness Score: -0.54

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