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ID: ALA575294
Max Phase: Preclinical
Molecular Formula: C12H12BrNO3
Molecular Weight: 298.14
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=C(Cc1ccc(Br)cc1)N[C@H]1CCOC1=O
Standard InChI: InChI=1S/C12H12BrNO3/c13-9-3-1-8(2-4-9)7-11(15)14-10-5-6-17-12(10)16/h1-4,10H,5-7H2,(H,14,15)/t10-/m0/s1
Standard InChI Key: ARMCPRYGJUZWON-JTQLQIEISA-N
Associated Targets(non-human)
Transcriptional activator protein traR 147 Activities
Transcriptional activator protein lasR 432 Activities
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Pseudomonas aeruginosa 123386 Activities
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Transcriptional activator protein luxR 400 Activities
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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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 298.14 | Molecular Weight (Monoisotopic): 297.0001 | AlogP: 1.42 | #Rotatable Bonds: 3 |
| Polar Surface Area: 55.40 | Molecular Species: NEUTRAL | HBA: 3 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 11.71 | CX Basic pKa: | CX LogP: 1.52 | CX LogD: 1.52 |
| Aromatic Rings: 1 | Heavy Atoms: 17 | QED Weighted: 0.86 | Np Likeness Score: -0.66 |
References
| 1. Ahumedo M, Díaz A, Vivas-Reyes R.. (2010) Theoretical and structural analysis of the active site of the transcriptional regulators LasR and TraR, using molecular docking methodology for identifying potential analogues of acyl homoserine lactones (AHLs) with anti-quorum sensing activity., 45 (2): [PMID:19945196] [10.1016/j.ejmech.2009.11.004] |
| 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] |
| 3. Capilato JN, Philippi SV, Reardon T, McConnell A, Oliver DC, Warren A, Adams JS, Wu C, Perez LJ.. (2017) Development of a novel series of non-natural triaryl agonists and antagonists of the Pseudomonas aeruginosa LasR quorum sensing receptor., 25 (1): [PMID:27825554] [10.1016/j.bmc.2016.10.021] |
| 4. 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] |
| 5. Hossain MA, Sattenapally N, Parikh HI, Li W, Rumbaugh KP, German NA.. (2020) Design, synthesis, and evaluation of compounds capable of reducing Pseudomonas aeruginosa virulence., 185 [PMID:31706639] [10.1016/j.ejmech.2019.111800] |
| 6. Chbib C.. (2020) Impact of the structure-activity relationship of AHL analogues on quorum sensing in Gram-negative bacteria., 28 (3): [PMID:31918952] [10.1016/j.bmc.2019.115282] |
| 7. 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):