2-(5-((4-chlorophenylthio)methyl)-1,3,4-thiadiazol-2-ylamino)-5-methylbenzenesulfonic acid

ID: ALA573503

PubChem CID: 340092

Max Phase: Preclinical

Molecular Formula: C16H14ClN3O3S3

Molecular Weight: 427.96

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-369693 | NSC369693|CHEMBL573503|NSC-369693|BDBM50300687|2-((5-(((4-Chlorophenyl)thio)methyl)-1,3,4-thiadiazol-2-yl)amino)-5-methylbenzenesulfonic acid|2-(5-((4-chlorophenylthio)methyl)-1,3,4-thiadiazol-2-ylamino)-5-methylbenzenesulfonic acid|2-[[5-[(4-chlorophenyl)sulfanylmethyl]-1,3,4-thiadiazol-2-yl]amino]-5-methyl-benzenesulfonic acid

Canonical SMILES:  Cc1ccc(Nc2nnc(CSc3ccc(Cl)cc3)s2)c(S(=O)(=O)O)c1

Standard InChI:  InChI=1S/C16H14ClN3O3S3/c1-10-2-7-13(14(8-10)26(21,22)23)18-16-20-19-15(25-16)9-24-12-5-3-11(17)4-6-12/h2-8H,9H2,1H3,(H,18,20)(H,21,22,23)

Standard InChI Key:  LFAIDABUOLWUEQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    2.3694    0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3682   -0.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0831   -0.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7995   -0.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7966    0.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0813    0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829   -1.5735    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3683   -1.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7972   -1.9862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2860   -1.3598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6534   -0.7476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9392   -0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9376    0.4883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1529    0.7430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3318    0.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1534   -0.5919    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1568    0.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696    0.7894    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3946    0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8048    1.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291    1.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0421    0.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6249    0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021    0.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8671    0.7857    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5095    0.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12 13  2  0
  1  2  2  0
  3  7  1  0
  3  4  2  0
  7  8  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
 15 17  1  0
  7  9  2  0
 17 18  1  0
  4  5  1  0
 18 19  1  0
  7 10  2  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
 21 22  2  0
  5  6  2  0
 22 23  1  0
  2 11  1  0
 23 24  2  0
 24 19  1  0
  6  1  1  0
 22 25  1  0
  5 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA573503

   2-((5-(((4-Chlorophenyl)thio)methyl)-1,3,4-thiadiazol-2-yl)amino)-5-methylbenzenesulfonic acid

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: 427.96

Molecular Weight (Monoisotopic): 426.9886

AlogP: 4.78

#Rotatable Bonds: 6

Polar Surface Area: 92.18

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -2.47

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: 1.88

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.43

Np Likeness Score: -2.13

References

1. Miguet L, Zervosen A, Gerards T, Pasha FA, Luxen A, Distèche-Nguyen M, Thomas A..  (2009)  Discovery of new inhibitors of resistant Streptococcus pneumoniae penicillin binding protein (PBP) 2x by structure-based virtual screening.,  52  (19): [PMID:19746934] [10.1021/jm900625q]

Source

Source(1):

• Scientific Literature