2-(4,5-Dibromo-1H-pyrrole-2-carboxamido)-N-hydroxybenzo[d]thiazole-6-carboxamide

ID: ALA4877862

PubChem CID: 152337049

Max Phase: Preclinical

Molecular Formula: C13H8Br2N4O3S

Molecular Weight: 460.11

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc2nc(NC(=O)c3cc(Br)c(Br)[nH]3)sc2c1

Standard InChI:  InChI=1S/C13H8Br2N4O3S/c14-6-4-8(16-10(6)15)12(21)18-13-17-7-2-1-5(11(20)19-22)3-9(7)23-13/h1-4,16,22H,(H,19,20)(H,17,18,21)

Standard InChI Key:  WWQGRJKCRKPKOX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   17.9449  -11.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6546  -11.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6517  -10.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9431   -9.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2369  -11.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2381  -10.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4576  -10.0162    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.9739  -10.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4556  -11.3447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1597  -10.6786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7521   -9.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9349   -9.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1616   -9.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4556   -9.3036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6781   -9.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6769  -10.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4538  -10.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0147  -10.8547    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.0176   -9.0738    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   19.3579   -9.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0672  -10.2637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3548   -9.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7733   -9.8524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 12  2  0
 16 18  1  0
 15 19  1  0
  3 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877862

   ---

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: 460.11

Molecular Weight (Monoisotopic): 457.8684

AlogP: 3.52

#Rotatable Bonds: 3

Polar Surface Area: 107.11

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.90

CX Basic pKa: ┄

CX LogP: 2.97

CX LogD: 2.96

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.35

Np Likeness Score: -1.41

References

1. Durcik M, Nyerges Á, Skok Ž, Skledar DG, Trontelj J, Zidar N, Ilaš J, Zega A, Cruz CD, Tammela P, Welin M, Kimbung YR, Focht D, Benek O, Révész T, Draskovits G, Szili PÉ, Daruka L, Pál C, Kikelj D, Mašič LP, Tomašič T..  (2021)  New dual ATP-competitive inhibitors of bacterial DNA gyrase and topoisomerase IV active against ESKAPE pathogens.,  213  [PMID:33524686] [10.1016/j.ejmech.2021.113200]

Source

Source(1):

• Scientific Literature