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ID: ALA1569494
Max Phase: Preclinical
Molecular Formula: C12H11NO6
Molecular Weight: 265.22
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): Dimethyl 2-(2-Nitrobenzylidene)Malonate
Synonyms from Alternative Forms(1):
Canonical SMILES: COC(=O)C(=Cc1ccccc1[N+](=O)[O-])C(=O)OC
Standard InChI: InChI=1S/C12H11NO6/c1-18-11(14)9(12(15)19-2)7-8-5-3-4-6-10(8)13(16)17/h3-7H,1-2H3
Standard InChI Key: LKLMASCOTOBEMT-UHFFFAOYSA-N
Associated Targets(Human)
microRNA 21 64692 Activities
Microtubule-associated protein tau 95507 Activities
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Neuropeptide S receptor 15785 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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ATPase family AAA domain-containing protein 5 122566 Activities
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Vitamin D receptor 26531 Activities
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DNA polymerase iota 116820 Activities
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HepG2 196354 Activities
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Mothers against decapentaplegic homolog 3 68039 Activities
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Geminin 128009 Activities
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DNA dC->dU-editing enzyme APOBEC-3G 12481 Activities
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Ataxin-2 54410 Activities
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Glucagon-like peptide 1 receptor 111429 Activities
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Glycoprotein hormones alpha chain 29278 Activities
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Tyrosyl-DNA phosphodiesterase 1 345557 Activities
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Isocitrate dehydrogenase [NADP] cytoplasmic 40980 Activities
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TAR DNA-binding protein 43 40113 Activities
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Parathyroid hormone receptor 47172 Activities
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DNA-(apurinic or apyrimidinic site) lyase 38016 Activities
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Histone deacetylase 8 4516 Activities
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Histone deacetylase 6 20808 Activities
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Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 735 Activities
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Histone deacetylase 1 10854 Activities
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Associated Targets(non-human)
Saccharomyces cerevisiae 19171 Activities
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Thioredoxin glutathione reductase 28579 Activities
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Nonstructural protein 1 33327 Activities
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Beta-lactamase AmpC 62480 Activities
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Nuclear receptor ROR-gamma 89407 Activities
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Plasmodium falciparum 966862 Activities
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Thioredoxin reductase 1, cytoplasmic 45279 Activities
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Toll-like receptor 4 808 Activities
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RAW264.7 28094 Activities
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Toll-like receptor 1/2 222 Activities
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TLR7 and TLR8 70 Activities
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Toll-like receptor 3 13 Activities
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TLR2/TLR6 253 Activities
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Histone deacetylase 8 483 Activities
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Escherichia coli 133304 Activities
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Klebsiella pneumoniae 43867 Activities
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Candida albicans 78123 Activities
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Cryptococcus neoformans 21258 Activities
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Staphylococcus aureus 210822 Activities
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Acinetobacter baumannii 41033 Activities
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Pseudomonas aeruginosa 123386 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: 265.22 | Molecular Weight (Monoisotopic): 265.0586 | AlogP: 1.32 | #Rotatable Bonds: 4 |
| Polar Surface Area: 95.74 | Molecular Species: | HBA: 6 | HBD: 0 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 2.42 | CX LogD: 2.42 |
| Aromatic Rings: 1 | Heavy Atoms: 19 | QED Weighted: 0.20 | Np Likeness Score: -0.66 |
References
| 1. PubChem BioAssay data set, |
| 2. Zhang S, Cheng K, Wang X, Yin H.. (2012) Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors., 20 (20): [PMID:22985959] [10.1016/j.bmc.2012.08.022] |
| 3. Ballante F, Reddy DR, Zhou NJ, Marshall GR.. (2017) Structural insights of SmKDAC8 inhibitors: Targeting Schistosoma epigenetics through a combined structure-based 3D QSAR, in vitro and synthesis strategy., 25 (7): [PMID:28259528] [10.1016/j.bmc.2017.02.020] |
| 4. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH NCI Diversity Set V, [10.6019/CHEMBL4296182] |
Source
Source(3):