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

ID: ALA2417885

PubChem CID: 72163845

Max Phase: Preclinical

Molecular Formula: C22H22Br3N3O3

Molecular Weight: 616.15

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  HDBDOGUHEIXQGP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    7.5858  -15.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5858  -16.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2911  -16.9547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9964  -16.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9964  -15.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2911  -15.3203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7017  -15.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4085  -15.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1169  -15.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1197  -14.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4082  -14.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7027  -14.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8769  -15.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8745  -14.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5844  -14.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5824  -13.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8729  -12.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1641  -13.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1696  -14.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8787  -16.9598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8281  -14.1095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5351  -14.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2435  -14.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9505  -14.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6589  -14.1141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3660  -14.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6602  -13.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8232  -15.7461    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.4077  -13.2893    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.2891  -12.8715    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.8695  -12.0573    0.0000 O   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
 10 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
  9 28  1  0
 11 29  1  0
 16 30  1  0
 17 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417885

   3-[(3-bromo-4-hydroxyphenyl)methyl]-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: 616.15

Molecular Weight (Monoisotopic): 612.9211

AlogP: 5.35

#Rotatable Bonds: 8

Polar Surface Area: 78.45

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.09

CX Basic pKa: 9.28

CX LogP: 3.55

CX LogD: 3.00

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: -0.21

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