(5Z)-2-(Benzodthiazol-2-ylimino)-5-((1-methyl-5-nitro-1Himidazol-2-yl)methylene)thiazolidin-4-one

ID: ALA2297972

PubChem CID: 136245257

Max Phase: Preclinical

Molecular Formula: C16H11N5O3S2

Molecular Weight: 385.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(/C=C2\S/C(=N/c3nc4ccccc4s3)NC2=O)ccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C16H11N5O3S2/c1-20-9(6-7-13(20)21(23)24)8-12-14(22)18-16(26-12)19-15-17-10-4-2-3-5-11(10)25-15/h2-8H,1H3,(H,17,18,19,22)/b12-8-

Standard InChI Key:  RUFDUSQRVSLRGT-WQLSENKSSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   23.8472  -19.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4962  -20.3718    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.1663  -19.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9312  -19.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1159  -19.1083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4258  -18.4754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9809  -19.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4482  -20.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0962  -20.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4417  -19.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4538  -18.8900    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.6623  -19.9490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1781  -21.3459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8297  -21.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5001  -21.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2627  -20.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8159  -22.6596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5156  -23.0819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1004  -23.0543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1909  -19.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6804  -18.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3611  -17.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5525  -17.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0643  -18.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3863  -19.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3957  -21.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  4  6  2  0
  3  7  2  0
  7  8  1  0
  1  9  2  0
  9 10  1  0
 10 11  1  0
 11 21  1  0
 20 12  1  0
 12 10  2  0
  8 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  8  2  0
 17 18  2  0
 17 19  1  0
 14 17  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 13 26  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2297972

   ---

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: 385.43

Molecular Weight (Monoisotopic): 385.0303

AlogP: 3.43

#Rotatable Bonds: 3

Polar Surface Area: 102.42

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.61

CX Basic pKa: ┄

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.42

Np Likeness Score: -1.87

References

1. Hosseinzadeh N, Hasani M, Foroumadi A, Nadri H, Emami S, Samadi N, Faramarzi MA, Saniee P, Siavoshi F, Abadian N, Mahmoudjanlou Y, Sakhteman A, Moradi A, Shafiee A.  (2013)  5-Nitro-heteroarylidene analogs of 2-thiazolylimino-4-thiazolidinones as a novel series of antibacterial agents,  22  (5): [10.1007/s00044-012-0224-6]

Source

Source(1):

• Scientific Literature