2-(4-(4,5-dichloro-1H-pyrrole-2-carboxamido)-3-isobutoxybenzamido)acetic acid

ID: ALA5281739

Max Phase: Preclinical

Molecular Formula: C18H19Cl2N3O5

Molecular Weight: 428.27

Names and Identifiers

Canonical SMILES:  CC(C)COc1cc(C(=O)NCC(=O)O)ccc1NC(=O)c1cc(Cl)c(Cl)[nH]1

Standard InChI:  InChI=1S/C18H19Cl2N3O5/c1-9(2)8-28-14-5-10(17(26)21-7-15(24)25)3-4-12(14)23-18(27)13-6-11(19)16(20)22-13/h3-6,9,22H,7-8H2,1-2H3,(H,21,26)(H,23,27)(H,24,25)

Standard InChI Key:  ZBPICFMFEFJSDY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.3625    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3520    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639    1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3538    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625    0.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0771   -0.0040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3538   -0.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7831   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3538   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    0.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5064   -0.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    1.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5926   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3994   -0.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8118   -0.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2599    0.3314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6370   -0.2815    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8120   -1.7105    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7785    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7785    2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931    1.2373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2078    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9224    1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6370    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9224    0.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  2  0
 16 14  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 14  1  0
 18 20  1  0
 17 21  1  0
  3 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281739

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 428.27

Molecular Weight (Monoisotopic): 427.0702

AlogP: 3.42

#Rotatable Bonds: 8

Polar Surface Area: 120.52

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.15

CX Basic pKa: ┄

CX LogP: 2.63

CX LogD: -0.84

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.51

Np Likeness Score: -1.10

References

1. Dighe SN, Collet TA..  (2020)  Recent advances in DNA gyrase-targeted antimicrobial agents.,  199  [PMID:32460040] [10.1016/j.ejmech.2020.112326]

Source

Source(1):

• Scientific Literature