| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ID: ALA193493
Max Phase: Preclinical
Molecular Formula: C5H8O4
Molecular Weight: 132.12
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): (S)-4,5-Dihydroxypentanedione
Synonyms from Alternative Forms(1):
Canonical SMILES: CC(=O)C(=O)[C@@H](O)CO
Standard InChI: InChI=1S/C5H8O4/c1-3(7)5(9)4(8)2-6/h4,6,8H,2H2,1H3/t4-/m0/s1
Standard InChI Key: UYTRITJAZOPLCZ-BYPYZUCNSA-N
Associated Targets(non-human)
Vibrio harveyi 399 Activities
Bacillus cereus 7522 Activities
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Autoinducer 2-binding periplasmic protein luxP 60 Activities
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Pseudomonas aeruginosa 123386 Activities
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Molecule Features
| Natural Product: Yes | 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: 132.12 | Molecular Weight (Monoisotopic): 132.0423 | AlogP: -1.50 | #Rotatable Bonds: 3 |
| Polar Surface Area: 74.60 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 12.48 | CX Basic pKa: | CX LogP: -0.90 | CX LogD: -0.90 |
| Aromatic Rings: 0 | Heavy Atoms: 9 | QED Weighted: 0.46 | Np Likeness Score: 1.13 |
References
| 1. Lowery CA, McKenzie KM, Qi L, Meijler MM, Janda KD.. (2005) Quorum sensing in Vibrio harveyi: probing the specificity of the LuxP binding site., 15 (9): [PMID:15837332] [10.1016/j.bmcl.2005.02.069] |
| 2. Frezza M, Soulère L, Balestrino D, Gohar M, Deshayes C, Queneau Y, Forestier C, Doutheau A.. (2007) Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of bacterial quorum sensing autoinducer AI-2., 17 (5): [PMID:17169556] [10.1016/j.bmcl.2006.11.076] |
| 3. Ganin H, Tang X, Meijler MM.. (2009) Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs., 19 (14): [PMID:19394822] [10.1016/j.bmcl.2009.03.163] |
| 4. Kadirvel M, Stimpson WT, Moumene-Afifi S, Arsic B, Glynn N, Halliday N, Williams P, Gilbert P, McBain AJ, Freeman S, Gardiner JM.. (2010) Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer., 20 (8): [PMID:20307979] [10.1016/j.bmcl.2010.02.064] |
| 5. Ascenso OS, Marques JC, Santos AR, Xavier KB, Ventura MR, Maycock CD.. (2011) An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing., 19 (3): [PMID:21216605] [10.1016/j.bmc.2010.12.036] |
| 6. 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] |
| 7. Rui F, Marques JC, Miller ST, Maycock CD, Xavier KB, Ventura MR.. (2012) Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli., 20 (1): [PMID:22137598] [10.1016/j.bmc.2011.11.007] |
Source
Source(1):