4-(2-((6-((Cyanomethyl)carbamoyl)-2-(3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamido)benzo[d]thiazol-4-yl)oxy)ethyl)morpholin-4-ium chloride

ID: ALA4876030

PubChem CID: 164627023

Max Phase: Preclinical

Molecular Formula: C22H23Cl3N6O4S

Molecular Weight: 537.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1[nH]c(C(=O)Nc2nc3c(OCCN4CCOCC4)cc(C(=O)NCC#N)cc3s2)c(Cl)c1Cl.Cl

Standard InChI:  InChI=1S/C22H22Cl2N6O4S.ClH/c1-12-16(23)17(24)19(27-12)21(32)29-22-28-18-14(34-9-6-30-4-7-33-8-5-30)10-13(11-15(18)35-22)20(31)26-3-2-25;/h10-11,27H,3-9H2,1H3,(H,26,31)(H,28,29,32);1H

Standard InChI Key:  RBPRMPXFSQQPIS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
    8.8648  -20.8792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3119  -19.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0283  -18.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0254  -18.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3101  -17.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5972  -18.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5984  -18.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8104  -17.8777    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3221  -18.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8084  -19.2189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5002  -18.5465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887  -17.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637  -17.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5021  -17.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7799  -17.1584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9949  -17.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938  -18.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781  -18.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3253  -18.7242    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.7383  -17.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4544  -18.1277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7352  -16.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304  -19.2802    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3282  -16.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3075  -20.2036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0198  -20.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0154  -21.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7276  -21.8612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7180  -22.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4261  -23.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1452  -22.6939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1515  -21.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4388  -21.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1672  -17.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8832  -18.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6001  -18.5298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  7  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 13  2  0
 17 19  1  0
  4 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 16 24  1  0
  2 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 21 34  1  0
 34 35  1  0
 35 36  3  0
M  END

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: 537.43

Molecular Weight (Monoisotopic): 536.0800

AlogP: 3.46

#Rotatable Bonds: 8

Polar Surface Area: 132.37

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.96

CX Basic pKa: 6.51

CX LogP: 2.55

CX LogD: 2.50

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.38

Np Likeness Score: -2.14

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