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

ID: ALA4540457

PubChem CID: 155549622

Max Phase: Preclinical

Molecular Formula: C23H25N5O3S

Molecular Weight: 451.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCN1CCN(Cc2ccc([N+](=O)[O-])cc2)CC1)Nc1nc(-c2ccccc2)cs1

Standard InChI:  InChI=1S/C23H25N5O3S/c29-22(25-23-24-21(17-32-23)19-4-2-1-3-5-19)10-11-26-12-14-27(15-13-26)16-18-6-8-20(9-7-18)28(30)31/h1-9,17H,10-16H2,(H,24,25,29)

Standard InChI Key:  NEQCYYNLTGTYBL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   38.1932   -3.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6054   -2.9868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.1932   -2.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3681   -2.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9555   -2.9868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.4303   -2.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8417   -2.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6661   -2.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0815   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6679   -0.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8387   -0.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4311   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1305   -2.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7169   -3.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8920   -3.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4825   -4.4202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4805   -2.9902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6576   -4.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1706   -3.7586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3862   -4.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3874   -4.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1725   -5.0908    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.7220   -3.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8082   -2.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1402   -2.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3856   -2.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3032   -3.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9721   -3.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0786   -0.1290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.6654    0.5877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.9085   -0.1304    0.0000 O   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
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  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
 21 24  1  0
 30 31  2  0
 30 32  1  0
 11 30  1  0
M  CHG  2  30   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4540457

   ---

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: 451.55

Molecular Weight (Monoisotopic): 451.1678

AlogP: 3.86

#Rotatable Bonds: 8

Polar Surface Area: 91.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.04

CX Basic pKa: 7.17

CX LogP: 3.85

CX LogD: 3.89

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.41

Np Likeness Score: -2.13

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