2-(3,4-Dichloro-N-ethyl-5-methyl-1H-pyrrole-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

ID: ALA4874918

PubChem CID: 148100605

Max Phase: Preclinical

Molecular Formula: C16H13Cl2N3O3S

Molecular Weight: 398.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN(C(=O)c1[nH]c(C)c(Cl)c1Cl)c1nc2ccc(C(=O)O)cc2s1

Standard InChI:  InChI=1S/C16H13Cl2N3O3S/c1-3-21(14(22)13-12(18)11(17)7(2)19-13)16-20-9-5-4-8(15(23)24)6-10(9)25-16/h4-6,19H,3H2,1-2H3,(H,23,24)

Standard InChI Key:  JPIPEYYUZKTTCM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   19.3729  -15.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0826  -14.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0798  -13.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3711  -13.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6649  -14.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6661  -13.8412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8856  -13.5862    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.4019  -14.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8836  -14.9147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5877  -14.2487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1801  -13.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3629  -13.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5897  -12.8333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8836  -12.8737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1061  -13.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1049  -13.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8818  -14.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4427  -14.4247    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.7859  -13.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4952  -13.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7829  -12.6106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1318  -14.9755    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.4456  -12.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1781  -14.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5857  -15.6641    0.0000 C   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
  3 19  1  0
 19 20  1  0
 19 21  2  0
 17 22  1  0
 15 23  1  0
 10 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874918

   ---

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: 398.27

Molecular Weight (Monoisotopic): 397.0055

AlogP: 4.60

#Rotatable Bonds: 4

Polar Surface Area: 86.29

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.62

CX Basic pKa: ┄

CX LogP: 4.18

CX LogD: 0.84

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -1.86

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