2,4-dibromo-6-((2-nitrobenzamido)methyl)phenyl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoate

ID: ALA3421669

PubChem CID: 118735092

Max Phase: Preclinical

Molecular Formula: C22H17Br2N3O7

Molecular Weight: 595.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCN1C(=O)C=CC1=O)Oc1c(Br)cc(Br)cc1CNC(=O)c1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C22H17Br2N3O7/c23-14-10-13(12-25-22(31)15-4-1-2-5-17(15)27(32)33)21(16(24)11-14)34-20(30)6-3-9-26-18(28)7-8-19(26)29/h1-2,4-5,7-8,10-11H,3,6,9,12H2,(H,25,31)

Standard InChI Key:  GBSPCDOSPAOGOD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -6.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5843   -7.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808   -8.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1824   -7.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1876   -6.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4915   -5.2692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5278   -5.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4978   -4.0692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -0.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990    0.7364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4525    1.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4523    0.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6978   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2317   -0.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3324   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6991    2.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  3  8  1  0
  1  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  2  0
 19 21  1  0
 18 19  1  0
  7 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 27  1  0
 31 32  2  0
 28 33  2  0
 12 34  2  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3421669

   ---

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: 595.20

Molecular Weight (Monoisotopic): 592.9433

AlogP: 3.66

#Rotatable Bonds: 9

Polar Surface Area: 135.92

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.97

CX Basic pKa: ┄

CX LogP: 3.67

CX LogD: 3.67

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.15

Np Likeness Score: -1.01

References

1. 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