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ID: ALA198759
Max Phase: Preclinical
Molecular Formula: C16H18N2OS
Molecular Weight: 286.40
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): Pifithrin-Alpha
Synonyms from Alternative Forms(1):
Canonical SMILES: Cc1ccc(C(=O)Cn2c3c(sc2=N)CCCC3)cc1
Standard InChI: InChI=1S/C16H18N2OS/c1-11-6-8-12(9-7-11)14(19)10-18-13-4-2-3-5-15(13)20-16(18)17/h6-9,17H,2-5,10H2,1H3
Standard InChI Key: OLTZHXYLLRJLST-UHFFFAOYSA-N
Associated Targets(Human)
TP53 Tchem Cellular tumor antigen p53 (48468 Activities)
MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)
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SMN1 Tchem Survival motor neuron protein (34246 Activities)
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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)
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MAPT Tclin Microtubule-associated protein tau (95507 Activities)
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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)
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MAPK1 Tchem MAP kinase ERK2 (25055 Activities)
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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
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GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)
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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)
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ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)
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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)
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HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
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Associated Targets(non-human)
Mus musculus (284745 Activities)
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Luciferin 4-monooxygenase (66902 Activities)
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luc Luciferase (1637 Activities)
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Rorc Nuclear receptor ROR-gamma (89407 Activities)
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lef Anthrax lethal factor (7585 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: 286.40 | Molecular Weight (Monoisotopic): 286.1140 | AlogP: 3.10 | #Rotatable Bonds: 3 |
| Polar Surface Area: 45.85 | Molecular Species: BASE | HBA: 4 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 3 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 13.13 | CX Basic pKa: 8.84 | CX LogP: 3.56 | CX LogD: 2.15 |
| Aromatic Rings: 2 | Heavy Atoms: 20 | QED Weighted: 0.87 | Np Likeness Score: -1.43 |
References
| 1. Barchéchath SD, Tawatao RI, Corr M, Carson DA, Cottam HB.. (2005) Inhibitors of apoptosis in lymphocytes: synthesis and biological evaluation of compounds related to pifithrin-alpha., 48 (20): [PMID:16190767] [10.1021/jm0502034] |
| 2. Auld DS, Southall NT, Jadhav A, Johnson RL, Diller DJ, Simeonov A, Austin CP, Inglese J.. (2008) Characterization of chemical libraries for luciferase inhibitory activity., 51 (8): [PMID:18363348] [10.1021/jm701302v] |
| 3. Strom E, Sathe S, Komarov PG, Chernova OB, Pavlovska I, Shyshynova I, Bosykh DA, Burdelya LG, Macklis RM, Skaliter R, Komarova EA, Gudkov AV.. (2006) Small-molecule inhibitor of p53 binding to mitochondria protects mice from gamma radiation., 2 (9): [PMID:16862141] [10.1038/nchembio809] |
| 4. PubChem BioAssay data set, |
| 5. PubChem BioAssay data set, |
| 6. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius. (2021) HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators, [10.6019/CHEMBL4808148] |
Source
Source(3):