N-(4-(4-bromophenyl)thiazol-2-yl)-3-(4-(3-nitrobenzyl)piperazin-1-yl)propanamide

ID: ALA4558785

PubChem CID: 155557672

Max Phase: Preclinical

Molecular Formula: C23H24BrN5O3S

Molecular Weight: 530.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCN1CCN(Cc2cccc([N+](=O)[O-])c2)CC1)Nc1nc(-c2ccc(Br)cc2)cs1

Standard InChI:  InChI=1S/C23H24BrN5O3S/c24-19-6-4-18(5-7-19)21-16-33-23(25-21)26-22(30)8-9-27-10-12-28(13-11-27)15-17-2-1-3-20(14-17)29(31)32/h1-7,14,16H,8-13,15H2,(H,25,26,30)

Standard InChI Key:  AAFUQGDOXCUKMO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   24.1950   -3.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0200   -3.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4282   -2.7797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0200   -2.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1950   -2.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7781   -2.7797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9531   -2.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5437   -3.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7187   -3.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3050   -4.2132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3031   -2.7831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4800   -4.2143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9932   -3.5516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2128   -3.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2139   -4.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9950   -4.8880    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.5445   -3.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6306   -2.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9625   -2.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2079   -2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1254   -3.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7945   -3.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2532   -2.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6688   -2.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4932   -2.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9045   -1.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4950   -0.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6657   -0.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2539   -1.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7324   -1.3545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1482   -0.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1456   -2.0703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5384   -1.8759    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 14 17  1  0
  3 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 30 31  2  0
 30 32  1  0
 26 30  1  0
 20 33  1  0
M  CHG  2  30   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4558785

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 530.45

Molecular Weight (Monoisotopic): 529.0783

AlogP: 4.63

#Rotatable Bonds: 8

Polar Surface Area: 91.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.02

CX Basic pKa: 7.09

CX LogP: 4.63

CX LogD: 4.69

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: -2.31

References

1. Chen L, Chen H, Chen P, Zhang W, Wu C, Sun C, Luo W, Zheng L, Liu Z, Liang G..  (2019)  Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury.,  161  [PMID:30342423] [10.1016/j.ejmech.2018.09.068]

Source

Source(1):

• Scientific Literature