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

ID: ALA2417879

PubChem CID: 72163727

Max Phase: Preclinical

Molecular Formula: C23H22Br2N4O2

Molecular Weight: 546.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCCCOc1c(Br)cc(-c2c[nH]c(=O)c(Cc3c[nH]c4ccccc34)n2)cc1Br

Standard InChI:  InChI=1S/C23H22Br2N4O2/c1-26-7-4-8-31-22-17(24)9-14(10-18(22)25)21-13-28-23(30)20(29-21)11-15-12-27-19-6-3-2-5-16(15)19/h2-3,5-6,9-10,12-13,26-27H,4,7-8,11H2,1H3,(H,28,30)

Standard InChI Key:  KJZSBZUBGSFSLC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   22.0889  -14.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0889  -14.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7942  -15.3079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4995  -14.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4995  -14.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7942  -13.6735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2048  -13.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9115  -14.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6200  -13.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6228  -12.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9113  -12.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2058  -12.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3800  -13.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3776  -12.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3818  -15.3130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9108  -11.6425    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   26.3263  -14.0993    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   26.3312  -12.4628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0382  -12.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7466  -12.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4536  -12.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1620  -12.4673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8690  -12.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0335  -12.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7787  -11.6037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7114  -12.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9626  -11.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4173  -11.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6207  -11.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3723  -11.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9192  -12.5558    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
 14 24  2  0
 24 25  1  0
 25 27  1  0
 26 14  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417879

   5-[3,5-dibromo-4-[3-(methylamino)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: 546.26

Molecular Weight (Monoisotopic): 544.0110

AlogP: 5.02

#Rotatable Bonds: 8

Polar Surface Area: 82.80

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.89

CX Basic pKa: 10.03

CX LogP: 3.58

CX LogD: 1.39

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -0.25

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