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ID: ALA473592
Max Phase: Preclinical
Molecular Formula: C14H15NO4
Molecular Weight: 261.28
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=C(CC(=O)N[C@H]1CCOC1=O)Cc1ccccc1
Standard InChI: InChI=1S/C14H15NO4/c16-11(8-10-4-2-1-3-5-10)9-13(17)15-12-6-7-19-14(12)18/h1-5,12H,6-9H2,(H,15,17)/t12-/m0/s1
Standard InChI Key: SZKJWOMSLREKNK-LBPRGKRZSA-N
Associated Targets(Human)
NCI-H630 194 Activities
PC-3 62116 Activities
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Associated Targets(non-human)
Transcriptional activator protein traR 147 Activities
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Transcriptional activator protein lasR 432 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: 261.28 | Molecular Weight (Monoisotopic): 261.1001 | AlogP: 0.62 | #Rotatable Bonds: 5 |
| Polar Surface Area: 72.47 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 11.30 | CX Basic pKa: | CX LogP: 0.97 | CX LogD: 0.97 |
| Aromatic Rings: 1 | Heavy Atoms: 19 | QED Weighted: 0.62 | Np Likeness Score: -0.09 |
References
| 1. Oliver CM, Schaefer AL, Greenberg EP, Sufrin JR.. (2009) Microwave synthesis and evaluation of phenacylhomoserine lactones as anticancer compounds that minimally activate quorum sensing pathways in Pseudomonas aeruginosa., 52 (6): [PMID:19260689] [10.1021/jm8015377] |
| 2. 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] |
| 3. 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] |
| 4. 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] |
Source
Source(1):