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ID: ALA339587
Max Phase: Preclinical
Molecular Formula: C15H12O4
Molecular Weight: 256.26
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): 2',3,4-Trihydroxychalcone
Synonyms from Alternative Forms(1):
Canonical SMILES: O=C(/C=C/c1ccc(O)c(O)c1)c1ccccc1O
Standard InChI: InChI=1S/C15H12O4/c16-12-4-2-1-3-11(12)13(17)7-5-10-6-8-14(18)15(19)9-10/h1-9,16,18-19H/b7-5+
Standard InChI Key: PSYVAIWGYVDYHN-FNORWQNLSA-N
Associated Targets(Human)
Cyclooxygenase 1258 Activities
BXPC-3 2997 Activities
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BT-20 503 Activities
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Lysine-specific demethylase 4D-like 40243 Activities
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Histone-lysine N-methyltransferase MLL 17327 Activities
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microRNA 21 64692 Activities
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Microtubule-associated protein tau 95507 Activities
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MAP kinase ERK2 25055 Activities
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Neuropeptide S receptor 15785 Activities
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Lysosomal alpha-glucosidase 35701 Activities
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Lysine-specific demethylase 4A 52245 Activities
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Cellular tumor antigen p53 48468 Activities
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ATPase family AAA domain-containing protein 5 122566 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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Chromobox protein homolog 1 92434 Activities
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DNA polymerase iota 116820 Activities
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DNA polymerase eta 21678 Activities
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78 kDa glucose-regulated protein 3319 Activities
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DNA dC->dU-editing enzyme APOBEC-3F 14861 Activities
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Geminin 128009 Activities
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Glutaminase kidney isoform, mitochondrial 16997 Activities
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Ataxin-2 54410 Activities
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Glucagon-like peptide 1 receptor 111429 Activities
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Transcriptional regulator ERG 5589 Activities
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Nuclear factor erythroid 2-related factor 2 95332 Activities
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Tyrosyl-DNA phosphodiesterase 1 345557 Activities
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TAR DNA-binding protein 43 40113 Activities
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Histone-lysine N-methyltransferase NSD2 803 Activities
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Myocilin 24 Activities
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Associated Targets(non-human)
Arachidonate 5-lipoxygenase 2865 Activities
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Rattus norvegicus 775804 Activities
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Tyrosinase 3884 Activities
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Pyruvate kinase 6726 Activities
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Nuclear receptor ROR-gamma 89407 Activities
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Zinc finger protein mex-5 1676 Activities
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Thioredoxin glutathione reductase 28579 Activities
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Nonstructural protein 1 33327 Activities
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Ferritin light chain 43324 Activities
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Luciferin 4-monooxygenase 66902 Activities
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Cytoplasmic zinc-finger protein 1690 Activities
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Large T antigen 1457 Activities
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Thioredoxin reductase 1, cytoplasmic 45279 Activities
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Aberrant vpr protein 14595 Activities
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Cyclooxygenase 970 Activities
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Toll-like receptor 1/2 222 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: 256.26 | Molecular Weight (Monoisotopic): 256.0736 | AlogP: 2.70 | #Rotatable Bonds: 3 |
| Polar Surface Area: 77.76 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 3 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 7.19 | CX Basic pKa: | CX LogP: 3.63 | CX LogD: 3.21 |
| Aromatic Rings: 2 | Heavy Atoms: 19 | QED Weighted: 0.45 | Np Likeness Score: 0.64 |
References
| 1. Sogawa S, Nihro Y, Ueda H, Izumi A, Miki T, Matsumoto H, Satoh T.. (1993) 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors., 36 (24): [PMID:8254620] [10.1021/jm00076a019] |
| 2. Jun N, Hong G, Jun K.. (2007) Synthesis and evaluation of 2',4',6'-trihydroxychalcones as a new class of tyrosinase inhibitors., 15 (6): [PMID:17267225] [10.1016/j.bmc.2007.01.017] |
| 3. Padhye S, Ahmad A, Oswal N, Dandawate P, Rub RA, Deshpande J, Swamy KV, Sarkar FH.. (2010) Fluorinated 2'-hydroxychalcones as garcinol analogs with enhanced antioxidant and anticancer activities., 20 (19): [PMID:20729081] [10.1016/j.bmcl.2010.07.128] |
| 4. PubChem BioAssay data set, |
| 5. Sharma MC. (2013) Molecular modeling studies of substituted 3,4-dihydroxychalcone derivatives as 5-lipoxygenase and cyclooxygenase inhibitors, [10.1007/s00044-013-0745-7] |
| 6. (2014) Antagonists of the toll-like receptor 1/2 complex, |
| 7. Srinivasan B, Tonddast-Navaei S, Skolnick J.. (2017) Pocket detection and interaction-weighted ligand-similarity search yields novel high-affinity binders for Myocilin-OLF, a protein implicated in glaucoma., 27 (17): [PMID:28739043] [10.1016/j.bmcl.2017.07.035] |
Source
Source(3):