ID: ALA175848

Max Phase: Preclinical

Molecular Formula: C26H19NO4

Molecular Weight: 409.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(Nc1ccccc1C(=O)O)c1ccc(-c2ccccc2)c(Oc2ccccc2)c1

Standard InChI:  InChI=1S/C26H19NO4/c28-25(27-23-14-8-7-13-22(23)26(29)30)19-15-16-21(18-9-3-1-4-10-18)24(17-19)31-20-11-5-2-6-12-20/h1-17H,(H,27,28)(H,29,30)

Standard InChI Key:  RYMAXBJFTSZAJG-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: 409.44

Molecular Weight (Monoisotopic): 409.1314

AlogP: 6.10

#Rotatable Bonds: 6

Polar Surface Area: 75.63

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.55

CX Basic pKa:

CX LogP: 6.52

CX LogD: 3.16

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -0.73

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, Hüsecken K, Groh M, Negri M, Haupenthal J, Hartmann RW..  (2013)  Discovery of novel bacterial RNA polymerase inhibitors: pharmacophore-based virtual screening and hit optimization.,  56  (21): [PMID:24112046] [10.1021/jm400485e]

5. 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]

6. 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]

Source

Source(1):

• Scientific Literature