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

ID: ALA2417878

PubChem CID: 72163726

Max Phase: Preclinical

Molecular Formula: C24H24Br2N4O2

Molecular Weight: 560.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCCOc1c(Br)cc(-c2c[nH]c(=O)c(Cc3c[nH]c4ccccc34)n2)cc1Br

Standard InChI:  InChI=1S/C24H24Br2N4O2/c1-30(2)8-5-9-32-23-18(25)10-15(11-19(23)26)22-14-28-24(31)21(29-22)12-16-13-27-20-7-4-3-6-17(16)20/h3-4,6-7,10-11,13-14,27H,5,8-9,12H2,1-2H3,(H,28,31)

Standard InChI Key:  GYGWWRXWIAUDSU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   11.3788  -14.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3788  -15.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0840  -15.5762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7893  -15.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7893  -14.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0840  -13.9418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4946  -13.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2014  -14.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9098  -13.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9126  -13.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2012  -12.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4956  -13.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6699  -13.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6675  -13.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6717  -15.5813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2007  -11.9108    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.6161  -14.3676    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.6210  -12.7311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3281  -13.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0364  -12.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7435  -13.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4518  -12.7356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1589  -13.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4531  -11.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3234  -12.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0686  -11.8720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0012  -12.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2524  -11.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7071  -11.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9105  -11.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6621  -12.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2091  -12.8241    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
  2 15  2  0
 11 16  1  0
  9 17  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 14 25  2  0
 25 26  1  0
 26 28  1  0
 27 14  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417878

   5-[3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl]-3-(1H-indol-3-ylmethyl)-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: 560.29

Molecular Weight (Monoisotopic): 558.0266

AlogP: 5.36

#Rotatable Bonds: 8

Polar Surface Area: 74.01

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.82

CX Basic pKa: 9.24

CX LogP: 4.24

CX LogD: 2.51

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: -0.46

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