(E)-N-(5-(3-(4-chlorophenyl)acryloyl)-4-methylthiazol-2-yl)-4-nitrobenzamide

ID: ALA4559478

PubChem CID: 155557823

Max Phase: Preclinical

Molecular Formula: C20H14ClN3O4S

Molecular Weight: 427.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc(NC(=O)c2ccc([N+](=O)[O-])cc2)sc1C(=O)/C=C/c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C20H14ClN3O4S/c1-12-18(17(25)11-4-13-2-7-15(21)8-3-13)29-20(22-12)23-19(26)14-5-9-16(10-6-14)24(27)28/h2-11H,1H3,(H,22,23,26)/b11-4+

Standard InChI Key:  CQDKSIBUIOFCRH-NYYWCZLTSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    6.0381  -12.7655    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3711  -13.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254  -14.0285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4467  -14.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7011  -13.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9268  -14.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042  -12.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1163  -13.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3955  -12.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8196  -12.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5316  -13.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6596  -12.8357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9514  -13.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2442  -12.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504  -14.0606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2482  -12.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5419  -11.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8327  -12.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8343  -12.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412  -13.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5358  -14.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2470  -14.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9512  -14.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9398  -13.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2281  -12.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6638  -14.4184    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1255  -11.6049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178  -12.0135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1255  -10.7877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  1  2  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  4  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  2  0
 10 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
 11 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 11  1  0
 23 26  1  0
 27 28  2  0
 27 29  1  0
 18 27  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4559478

   ---

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: 427.87

Molecular Weight (Monoisotopic): 427.0394

AlogP: 5.16

#Rotatable Bonds: 6

Polar Surface Area: 102.20

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.00

CX Basic pKa: ┄

CX LogP: 5.13

CX LogD: 5.13

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.25

Np Likeness Score: -1.70

References

1. Sinha S, Manju SL, Doble M..  (2019)  Chalcone-Thiazole Hybrids: Rational Design, Synthesis, and Lead Identification against 5-Lipoxygenase.,  10  (10): [PMID:31620227] [10.1021/acsmedchemlett.9b00193]

Source

Source(1):

• Scientific Literature