ID: ALA178657

Max Phase: Preclinical

Molecular Formula: C18H19BrN2O5S

Molecular Weight: 455.33

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCN(CC)S(=O)(=O)c1cc(C(=O)Nc2ccccc2C(=O)O)ccc1Br

Standard InChI:  InChI=1S/C18H19BrN2O5S/c1-3-21(4-2)27(25,26)16-11-12(9-10-14(16)19)17(22)20-15-8-6-5-7-13(15)18(23)24/h5-11H,3-4H2,1-2H3,(H,20,22)(H,23,24)

Standard InChI Key:  VNOMZKMKBNFCMC-UHFFFAOYSA-N

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

Properties

Molecular Weight: 455.33

Molecular Weight (Monoisotopic): 454.0198

AlogP: 3.43

#Rotatable Bonds: 7

Polar Surface Area: 103.78

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.55

CX Basic pKa:

CX LogP: 3.91

CX LogD: 0.55

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -1.71

References

1. Nie Z, Perretta C, Lu J, Su Y, Margosiak S, Gajiwala KS, Cortez J, Nikulin V, Yager KM, Appelt K, Chu S..  (2005)  Structure-based design, synthesis, and study of potent inhibitors of beta-ketoacyl-acyl carrier protein synthase III as potential antimicrobial agents.,  48  (5): [PMID:15743201] [10.1021/jm049141s]

2. Singh S, Soni LK, Gupta MK, Prabhakar YS, Kaskhedikar SG..  (2008)  QSAR studies on benzoylaminobenzoic acid derivatives as inhibitors of beta-ketoacyl-acyl carrier protein synthase III.,  43  (5): [PMID:17707951] [10.1016/j.ejmech.2007.06.018]

3. Weidel E, de Jong JC, Brengel C, Storz MP, Braunshausen A, Negri M, Plaza A, Steinbach A, Müller R, Hartmann RW..  (2013)  Structure optimization of 2-benzamidobenzoic acids as PqsD inhibitors for Pseudomonas aeruginosa infections and elucidation of binding mode by SPR, STD NMR, and molecular docking.,  56  (15): [PMID:23834469] [10.1021/jm4006302]

4. Hinsberger S, de Jong JC, Groh M, Haupenthal J, Hartmann RW..  (2014)  Benzamidobenzoic acids as potent PqsD inhibitors for the treatment of Pseudomonas aeruginosa infections.,  76  [PMID:24589489] [10.1016/j.ejmech.2014.02.014]

5. Soukarieh F, Williams P, Stocks MJ, Cámara M..  (2018)  Pseudomonas aeruginosa Quorum Sensing Systems as Drug Discovery Targets: Current Position and Future Perspectives.,  61  (23): [PMID:29999316] [10.1021/acs.jmedchem.8b00540]

6. Wagner S, Sommer R, Hinsberger S, Lu C, Hartmann RW, Empting M, Titz A..  (2016)  Novel Strategies for the Treatment of Pseudomonas aeruginosa Infections.,  59  (13): [PMID:26804741] [10.1021/acs.jmedchem.5b01698]

Source

Source(1):

• Scientific Literature