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ID: ALA1170485
Max Phase: Preclinical
Molecular Formula: C13H12O2
Molecular Weight: 200.24
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (2): (R,S)-Goniothalamin | Rac-Goniothalamin
Synonyms from Alternative Forms(2):
Canonical SMILES: O=C1C=CCC(/C=C/c2ccccc2)O1
Standard InChI: InChI=1S/C13H12O2/c14-13-8-4-7-12(15-13)10-9-11-5-2-1-3-6-11/h1-6,8-10,12H,7H2/b10-9+
Standard InChI Key: RLGHFVLWYYVMQZ-MDZDMXLPSA-N
Associated Targets(Human)
MDA-MB-231 (73002 Activities)
HepG2 (196354 Activities)
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A549 (127892 Activities)
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HT-29 (80576 Activities)
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MCF7 (126967 Activities)
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KB (17409 Activities)
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UACC-62 (47335 Activities)
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786-0 (47912 Activities)
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NCI-H460 (60772 Activities)
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OVCAR-3 (48710 Activities)
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U-251 (51189 Activities)
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LMNA Tbio Prelamin-A/C (36751 Activities)
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HTT Tchem Huntingtin (19182 Activities)
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KMT2A Tchem Histone-lysine N-methyltransferase MLL (17327 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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RAB9A Tbio Ras-related protein Rab-9A (22488 Activities)
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MAPT Tclin Microtubule-associated protein tau (95507 Activities)
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H4 (3266 Activities)
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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
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|---|
JAK2 Tclin Tyrosine-protein kinase JAK2 (12915 Activities)
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|---|
NFE2L2 Tchem Nuclear factor erythroid 2-related factor 2 (95332 Activities)
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|---|
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
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|---|
ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)
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Jurkat (10389 Activities)
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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
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RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)
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|---|
POLI Tchem DNA polymerase iota (116820 Activities)
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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)
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|---|
HEK293 (82097 Activities)
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GMNN Tbio Geminin (128009 Activities)
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ATXN2 Tbio Ataxin-2 (54410 Activities)
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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)
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WRN Tbio Werner syndrome ATP-dependent helicase (8824 Activities)
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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)
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TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)
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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)
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HBL-100 (746 Activities)
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Associated Targets(non-human)
WEHI-164 (110 Activities)
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P388 (20296 Activities)
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Mus musculus (284745 Activities)
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Rorc Nuclear receptor ROR-gamma (89407 Activities)
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vpr Aberrant vpr protein (14595 Activities)
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Saccharomyces cerevisiae (19171 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: 200.24 | Molecular Weight (Monoisotopic): 200.0837 | AlogP: 2.57 | #Rotatable Bonds: 2 |
| Polar Surface Area: 26.30 | Molecular Species: NEUTRAL | HBA: 2 | HBD: 0 |
| #RO5 Violations: 0 | HBA (Lipinski): 2 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 3.22 | CX LogD: 3.22 |
| Aromatic Rings: 1 | Heavy Atoms: 15 | QED Weighted: 0.69 | Np Likeness Score: 2.29 |
References
| 1. Dumitrescu L, Mai Huong DT, Van Hung N, Crousse B, Bonnet-Delpon D.. (2010) Synthesis and cytotoxic activity of fluorinated analogues of Goniothalamus lactones. Impact of fluorine on oxidative processes., 45 (7): [PMID:20392543] [10.1016/j.ejmech.2010.03.032] |
| 2. Vendramini-Costa DB, de Castro IB, Ruiz AL, Marquissolo C, Pilli RA, de Carvalho JE.. (2010) Effect of goniothalamin on the development of Ehrlich solid tumor in mice., 18 (18): [PMID:20729093] [10.1016/j.bmc.2010.07.053] |
| 3. PubChem BioAssay data set, |
| 4. Lee SM, Lee WG, Kim YC, Ko H.. (2011) Synthesis and biological evaluation of α,β-unsaturated lactones as potent immunosuppressive agents., 21 (19): [PMID:21873054] [10.1016/j.bmcl.2011.08.020] |
| 5. Weber A, Döhl K, Sachs J, Nordschild ACM, Schröder D, Kulik A, Fischer T, Schmitt L, Teusch N, Pietruszka J.. (2017) Synthesis and cytotoxic activities of goniothalamins and derivatives., 25 (22): [PMID:28214230] [10.1016/j.bmc.2017.02.004] |
Source
Source(2):