N-(4-(Benzo[d]thiazol-2-ylthio)-3-chlorophenyl)-3-bromo-2-hydroxybenzamide

ID: ALA4293874

PubChem CID: 145988386

Max Phase: Preclinical

Molecular Formula: C20H12BrClN2O2S2

Molecular Weight: 491.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Sc2nc3ccccc3s2)c(Cl)c1)c1cccc(Br)c1O

Standard InChI:  InChI=1S/C20H12BrClN2O2S2/c21-13-5-3-4-12(18(13)25)19(26)23-11-8-9-16(14(22)10-11)27-20-24-15-6-1-2-7-17(15)28-20/h1-10,25H,(H,23,26)

Standard InChI Key:  FHLUNTRPMOXZED-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    7.3533   -8.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3522   -9.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0602  -10.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7699   -9.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7670   -8.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0584   -8.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4732   -8.5494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1824   -8.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8886   -8.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1855   -9.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5963   -8.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3020   -8.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2993   -7.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5851   -7.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8823   -7.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6441  -10.1919    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9367   -9.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8504   -8.9676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1884  -10.1121    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6420   -9.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0511   -8.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6467   -8.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8334   -8.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4261   -8.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8329   -9.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0600  -11.0100    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.5973   -9.7706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0110   -8.9491    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  9  1  0
  2 16  1  0
 16 17  1  0
 17 18  2  0
 18 21  1  0
 20 19  1  0
 19 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
  3 26  1  0
 11 27  1  0
 12 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4293874

   ---

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: 491.82

Molecular Weight (Monoisotopic): 489.9212

AlogP: 6.82

#Rotatable Bonds: 4

Polar Surface Area: 62.22

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.60

CX Basic pKa: 0.84

CX LogP: 7.15

CX LogD: 6.30

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.33

Np Likeness Score: -1.81

References

1. Kunkle T, Abdeen S, Salim N, Ray AM, Stevens M, Ambrose AJ, Victorino J, Park Y, Hoang QQ, Chapman E, Johnson SM..  (2018)  Hydroxybiphenylamide GroEL/ES Inhibitors Are Potent Antibacterials against Planktonic and Biofilm Forms of Staphylococcus aureus.,  61  (23): [PMID:30392371] [10.1021/acs.jmedchem.8b01293]

2. Ray AM, Salim N, Stevens M, Chitre S, Abdeen S, Washburn A, Sivinski J, O'Hagan HM, Chapman E, Johnson SM..  (2021)  Exploiting the HSP60/10 chaperonin system as a chemotherapeutic target for colorectal cancer.,  40  [PMID:33971488] [10.1016/j.bmc.2021.116129]

Source

Source(1):

• Scientific Literature