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

ID: ALA2417779

PubChem CID: 72163724

Max Phase: Preclinical

Molecular Formula: C21H20Br3N3O3

Molecular Weight: 602.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCCOc1c(Br)cc(-c2c[nH]c(=O)c(Cc3ccc(OC)c(Br)c3)n2)cc1Br

Standard InChI:  InChI=1S/C21H20Br3N3O3/c1-25-5-6-30-20-15(23)9-13(10-16(20)24)18-11-26-21(28)17(27-18)8-12-3-4-19(29-2)14(22)7-12/h3-4,7,9-11,25H,5-6,8H2,1-2H3,(H,26,28)

Standard InChI Key:  MFUGLRROJUFEHA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   18.3497   -6.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3497   -7.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0549   -7.7798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7602   -7.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7602   -6.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0549   -6.1454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4655   -6.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1723   -6.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8807   -6.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8835   -5.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1720   -4.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4665   -5.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6408   -6.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6384   -5.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3482   -4.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3462   -4.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6368   -3.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9279   -4.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9334   -4.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6425   -7.7850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1716   -4.1145    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   22.5870   -6.5713    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   22.5919   -4.9347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2989   -5.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0073   -4.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7144   -5.3467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4227   -4.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0529   -3.6966    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.6333   -2.8824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3392   -2.4708    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
 16 28  1  0
 17 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417779

   3-[(3-bromo-4-methoxyphenyl)methyl]-5-[3,5-dibromo-4-[2-(methylamino)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: 602.12

Molecular Weight (Monoisotopic): 598.9055

AlogP: 4.92

#Rotatable Bonds: 8

Polar Surface Area: 76.24

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.83

CX Basic pKa: 9.41

CX LogP: 4.28

CX LogD: 2.43

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -0.13

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