2,4-dibromo-6-((2-nitrobenzamido)methyl)phenyl 2-chlorobenzoate

ID: ALA1236450

PubChem CID: 44199338

Max Phase: Preclinical

Molecular Formula: C21H13Br2ClN2O5

Molecular Weight: 568.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Oc1c(Br)cc(Br)cc1CNC(=O)c1ccccc1[N+](=O)[O-])c1ccccc1Cl

Standard InChI:  InChI=1S/C21H13Br2ClN2O5/c22-13-9-12(11-25-20(27)15-6-2-4-8-18(15)26(29)30)19(16(23)10-13)31-21(28)14-5-1-3-7-17(14)24/h1-10H,11H2,(H,25,27)

Standard InChI Key:  WKUUVOPOQKZMFY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -1.2340   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9484   -2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9484   -2.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340   -3.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195   -2.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195   -2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1950   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1950   -0.8160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9095   -0.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9095    0.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1950    0.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1950    1.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9095    2.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6239    1.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6239    0.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3384    0.4215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6239   -0.8160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0529    0.8340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3384   -0.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340   -0.8160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9484   -0.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629   -0.8160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629   -1.6410    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340   -4.1160    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9484    0.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340    0.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340    1.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9484    2.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629    1.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629    0.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3774    0.4215    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1 20  1  0
  1  6  1  0
 23  2  1  0
  2  3  1  0
  3  4  2  0
 24  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  9  8  1  0
  9 17  2  0
 10  9  1  0
 10 15  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 19  1  0
 16 18  2  0
 21 20  1  0
 21 22  2  0
 21 25  1  0
 25 30  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
M  CHG  2  16   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1236450

   2,4-Dibromo-6-({[(2-nitrophenyl)carbonyl]amino}methyl)phenyl 2-chlorobenzoate

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: 568.61

Molecular Weight (Monoisotopic): 565.8880

AlogP: 5.92

#Rotatable Bonds: 6

Polar Surface Area: 98.54

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.59

CX Basic pKa: ┄

CX LogP: 6.52

CX LogD: 6.52

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.17

Np Likeness Score: -1.43

References

1. Lowery CA, Salzameda NT, Sawada D, Kaufmann GF, Janda KD..  (2010)  Medicinal chemistry as a conduit for the modulation of quorum sensing.,  53  (21): [PMID:20669927] [10.1021/jm901742e]

2. O'Brien KT, Noto JG, Nichols-O'Neill L, Perez LJ..  (2015)  Potent Irreversible Inhibitors of LasR Quorum Sensing in Pseudomonas aeruginosa.,  6  (2): [PMID:25699144] [10.1021/ml500459f]

Source

Source(1):

• Scientific Literature