4,6-dinitrobenzo[c][1,2,5]thiadiazole

ID: ALA206140

Cas Number: 16408-06-3

PubChem CID: 305451

Max Phase: Preclinical

Molecular Formula: C6H2N4O4S

Molecular Weight: 226.17

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4,6-Dinitrobenzo[C][1,2,5]Thiadiazole | 4,6-Dinitro-2,1,3-benzothiadiazole|16408-06-3|4,6-dinitrobenzo[c][1,2,5]thiadiazole|CHEMBL206140|5,7-dinitro-2,1,3-benzothiadiazole|NSC-202427|2,1,3-Benzothiadiazole, 4,6-dinitro-|NSC202427|TZ4RRX7H54|DTXSID90308123|BYLOIWCTRDPRTP-UHFFFAOYSA-N|BDBM50182130|AKOS000544790|4,6-Dinitro-2,1,3-benzothiadiazole #|NCI60_001699|PD181957

Canonical SMILES:  O=[N+]([O-])c1cc([N+](=O)[O-])c2nsnc2c1

Standard InChI:  InChI=1S/C6H2N4O4S/c11-9(12)3-1-4-6(8-15-7-4)5(2-3)10(13)14/h1-2H

Standard InChI Key:  BYLOIWCTRDPRTP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
   -4.0126   -3.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0138   -4.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2992   -4.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010   -2.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038   -3.0169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903   -3.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -4.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7952   -4.3554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3142   -3.6804    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3032   -2.0401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0177   -1.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5891   -1.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7302   -4.5162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7309   -5.3409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4442   -4.1032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  6  2  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  4  1  2  0
  6  7  1  0
 10 11  2  0
 10 12  1  0
  4 10  1  0
  2  3  2  0
  3  7  1  0
  1  2  1  0
 13 14  2  0
 13 15  1  0
  2 13  1  0
M  CHG  4  10   1  12  -1  13   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA206140

   4,6-Dinitro-2,1,3-benzothiadiazole

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: 226.17

Molecular Weight (Monoisotopic): 225.9797

AlogP: 1.51

#Rotatable Bonds: 2

Polar Surface Area: 112.06

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.00

CX LogD: 2.00

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.57

Np Likeness Score: -1.90

References

1. Andricopulo AD, Akoachere MB, Krogh R, Nickel C, McLeish MJ, Kenyon GL, Arscott LD, Williams CH, Davioud-Charvet E, Becker K..  (2006)  Specific inhibitors of Plasmodium falciparum thioredoxin reductase as potential antimalarial agents.,  16  (8): [PMID:16458512] [10.1016/j.bmcl.2006.01.027]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays