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ID: ALA1424665
Max Phase: Preclinical
Molecular Formula: C20H20N4O3
Molecular Weight: 364.41
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=[N+]([O-])c1cc(CN2CCN(c3ccccc3)CC2)c(O)c2ncccc12
Standard InChI: InChI=1S/C20H20N4O3/c25-20-15(13-18(24(26)27)17-7-4-8-21-19(17)20)14-22-9-11-23(12-10-22)16-5-2-1-3-6-16/h1-8,13,25H,9-12,14H2
Standard InChI Key: RWSKCMWORGMGJE-UHFFFAOYSA-N
Associated Targets(Human)
Prelamin-A/C 36751 Activities
Huntingtin 19182 Activities
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Ras-related protein Rab-9A 22488 Activities
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Survival motor neuron protein 34246 Activities
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Tyrosyl-DNA phosphodiesterase 1 345557 Activities
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Microtubule-associated protein tau 95507 Activities
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Aldehyde dehydrogenase 1A1 77053 Activities
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Lethal(3)malignant brain tumor-like protein 1 14536 Activities
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MAP kinase ERK2 25055 Activities
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Microphthalmia-associated transcription factor 3197 Activities
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Lysine-specific demethylase 4A 52245 Activities
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Nuclear factor erythroid 2-related factor 2 95332 Activities
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Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 93046 Activities
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Bromodomain adjacent to zinc finger domain protein 2B 56204 Activities
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ATPase family AAA domain-containing protein 5 122566 Activities
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A-375 9258 Activities
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DNA polymerase iota 116820 Activities
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Mothers against decapentaplegic homolog 3 68039 Activities
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HEK293 82097 Activities
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HeLa 62764 Activities
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Photoreceptor-specific nuclear receptor 502 Activities
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Geminin 128009 Activities
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Guanine nucleotide-binding protein G(s), subunit alpha 103405 Activities
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TAR DNA-binding protein 43 40113 Activities
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Alpha-synuclein 10960 Activities
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Isocitrate dehydrogenase [NADP] cytoplasmic 40980 Activities
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Associated Targets(non-human)
Heat shock factor protein 1 5445 Activities
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Putative fructose-1,6-bisphosphate aldolase 15559 Activities
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Nuclear receptor ROR-gamma 89407 Activities
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Nonstructural protein 1 33327 Activities
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ATP-dependent molecular chaperone HSP82 2186 Activities
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INS1 2867 Activities
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Serine/threonine-protein phosphatase 383 Activities
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Plasmodium falciparum 966862 Activities
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Tyrosine-protein phosphatase yopH 57 Activities
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Chlamydia trachomatis 699 Activities
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Yersinia pseudotuberculosis 544 Activities
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J774 3120 Activities
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Alpha trans-inducing protein (VP16) 945 Activities
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Chlamydia 5 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 |
|---|
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: 364.41 | Molecular Weight (Monoisotopic): 364.1535 | AlogP: 3.17 | #Rotatable Bonds: 4 |
| Polar Surface Area: 82.74 | Molecular Species: ACID | HBA: 6 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 5.77 | CX Basic pKa: 8.43 | CX LogP: 1.43 | CX LogD: 1.67 |
| Aromatic Rings: 3 | Heavy Atoms: 27 | QED Weighted: 0.57 | Np Likeness Score: -1.38 |
References
| 1. PubChem BioAssay data set, |
| 2. Enquist PA, Gylfe A, Hägglund U, Lindström P, Norberg-Scherman H, Sundin C, Elofsson M.. (2012) Derivatives of 8-hydroxyquinoline--antibacterial agents that target intra- and extracellular Gram-negative pathogens., 22 (10): [PMID:22525317] [10.1016/j.bmcl.2012.03.096] |
| 3. Joaquim AR, Gionbelli MP, Gosmann G, Fuentefria AM, Lopes MS, Fernandes de Andrade S.. (2021) Novel Antimicrobial 8-Hydroxyquinoline-Based Agents: Current Development, Structure-Activity Relationships, and Perspectives., 64 (22.0): [PMID:34779640] [10.1021/acs.jmedchem.1c01318] |
Source
Source(2):