PD-146176 : An organic heterotetracyclic compound that is 1H-indole which is ortho-fused to a 2H-1-benzothiopyran group at positions 2-3. It is an inhibitor of 15-lipoxygenase that limits atherosclerotic lesion development in rabbits. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 297589 |
| CHEMBL ID | 180917 |
| CHEBI ID | 173098 |
| SCHEMBL ID | 1986281 |
| MeSH ID | M0276930 |
| Synonym |
|---|
| pd146176 , |
| 6,11-dihydrothiochromeno[4,3-b]indole |
| CHEBI:173098 |
| 6,11-dihydro[1]benzothiopyrano[4,3-b]indole |
| [1]benzothiopyrano[4, 6,11-dihydro- |
| nsc168807 |
| nsc-168807 |
| 4079-26-9 |
| 6,3-b]indole |
| pd 146176, >=98% (hplc), solid |
| NCGC00165868-01 |
| EC-000.2427 |
| CHEMBL180917 , |
| bdbm50208823 |
| pd-146176 |
| pd 146176 , |
| SCHEMBL1986281 |
| AKOS024457313 |
| (1)benzothiopyrano(4,3-b)indole, 6,11-dihydro- |
| 5k2qda6f3s , |
| unii-5k2qda6f3s |
| nsc 168807 |
| 6,11-dihydro-5-thia-11-aza-benzo(a)fluorene |
| BCP24885 |
| 6,11-dihydro-[1]benzothiopyrano[4,3-b]indole |
| HY-103157 |
| benzothiopyrano(4,3-b)indole, 6,11-dihydro- |
| 6,11-dihydro(1)benzothiopyrano(4,3-b)indole |
| EX-A3327 |
| CS-0024982 |
| D94940 |
| DTXSID20961205 |
| AC-35656 |
| gtpl11390 |
| 6h,11h-thiochromeno[4,3-b]indole |
| AS-78067 |
| Role | Description |
|---|---|
| ferroptosis inhibitor | Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms. |
| EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor | A lipoxygenase inhibitor that interferes with the action of arachidonate 15-lipoxygenase (EC 1.13.11.33). |
| antiatherogenic agent | A cardiovascular drug that prevents atherogenesis, the accumulation of lipid-containing plaques on the innermost layers of the arteries. Compare with antiatherosclerotic agent. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| organic heterotetracyclic compound | |
| organosulfur heterocyclic compound | |
| organonitrogen heterocyclic compound | Any organonitrogen compound containing a cyclic component with nitrogen and at least one other element as ring member atoms. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, TYROSYL-DNA PHOSPHODIESTERASE | Homo sapiens (human) | Potency | 31.6228 | 0.0040 | 23.8416 | 100.0000 | AID485290 |
| phosphopantetheinyl transferase | Bacillus subtilis | Potency | 50.1187 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
| vitamin D3 receptor isoform VDRA | Homo sapiens (human) | Potency | 10.0000 | 0.3548 | 28.0659 | 89.1251 | AID504847 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 7.2334 | 0.0079 | 8.2332 | 1,122.0200 | AID2546; AID2551 |
| histone acetyltransferase KAT2A isoform 1 | Homo sapiens (human) | Potency | 22.3872 | 0.2512 | 15.8432 | 39.8107 | AID504327 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Polyunsaturated fatty acid lipoxygenase ALOX15 | Oryctolagus cuniculus (rabbit) | IC50 (µMol) | 2.9133 | 0.1100 | 3.2641 | 9.0330 | AID1587933; AID242641; AID286229 |
| Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) | IC50 (µMol) | 0.8100 | 0.0400 | 2.0998 | 10.0000 | AID1279095 |
| Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) | Ki | 3.8100 | 0.0100 | 1.7077 | 8.1000 | AID1250681; AID1331519 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| arachidonate 12(S)-lipoxygenase activity | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| iron ion binding | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| protein binding | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| phosphatidylinositol-4,5-bisphosphate binding | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| linoleate 13S-lipoxygenase activity | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| arachidonate 15-lipoxygenase activity | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| lipid droplet | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| cytosol | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| plasma membrane | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| cytoplasmic side of plasma membrane | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| membrane | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| plasma membrane | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| cytosol | Polyunsaturated fatty acid lipoxygenase ALOX15 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1331537 | Inhibition of 15-LOX-1 in mouse HT22 cells assessed as protection against glutamate-induced cell impedance at 1 uM cotreated with glutamate up to 16 hrs by real time cell viability assay | 2016 | European journal of medicinal chemistry, Oct-21, Volume: 122 | Design of a novel thiophene inhibitor of 15-lipoxygenase-1 with both anti-inflammatory and neuroprotective properties. |
| AID1250681 | Competitive inhibition of human 15-LOX1 using linoleic acid as substrate after 10 mins by Lineweaver-Burk plot analysis | 2015 | Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19 | Rational Development of a Potent 15-Lipoxygenase-1 Inhibitor with in Vitro and ex Vivo Anti-inflammatory Properties. |
| AID1331532 | Inhibition of 15-LOX-1 in mouse HT22 cells assessed as inhibition of glutamate-induced lipid peroxidation at 1 uM incubated for 14 to 16 hrs by BODIPY 581/591 C11 staining based FACS analysis | 2016 | European journal of medicinal chemistry, Oct-21, Volume: 122 | Design of a novel thiophene inhibitor of 15-lipoxygenase-1 with both anti-inflammatory and neuroprotective properties. |
| AID1331536 | Inhibition of 15-LOX-1 in mouse HT22 cells assessed as protection against glutamate-induced cell death by measuring increase in cell viability at 1 uM cotreated with glutamate measured for 16 to 20 hrs by MTT assay | 2016 | European journal of medicinal chemistry, Oct-21, Volume: 122 | Design of a novel thiophene inhibitor of 15-lipoxygenase-1 with both anti-inflammatory and neuroprotective properties. |
| AID1587933 | Inhibition of rabbit reticulocyte 15-LOX using [14C]-linoleic acid as substrate preincubated for 15 mins followed by substrate addition by RP-HPLC analysis | 2019 | Journal of medicinal chemistry, 05-09, Volume: 62, Issue:9 | Novel 15-Lipoxygenase-1 Inhibitor Protects Macrophages from Lipopolysaccharide-Induced Cytotoxicity. |
| AID242641 | Inhibitory concentration against isolated rabbit reticulocyte 15-lipoxygenase measured in the presence of linoleic acid | 2005 | Bioorganic & medicinal chemistry letters, Mar-01, Volume: 15, Issue:5 | Tryptamine and homotryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase. |
| AID286229 | Inhibition of 15LOX in rabbit reticulocytes by EIA assay | 2007 | Journal of natural products, May, Volume: 70, Issue:5 | Lipoxygenase inhibitory constituents of the fruits of noni (Morinda citrifolia) collected in Tahiti. |
| AID1279095 | Inhibition of human 12/15-LOX expressed in HEK293 cells after 30 mins by microplate reader analysis | 2016 | Bioorganic & medicinal chemistry, Mar-15, Volume: 24, Issue:6 | A potent and selective inhibitor targeting human and murine 12/15-LOX. |
| AID1331519 | Competitive inhibition of human 15-LOX-1 assessed as reduction in conversion of linoleic acid to 13(S)-HpODE incubated for 10 mins followed by linoleic acid addition by Lineweaver-Burk plot analysis | 2016 | European journal of medicinal chemistry, Oct-21, Volume: 122 | Design of a novel thiophene inhibitor of 15-lipoxygenase-1 with both anti-inflammatory and neuroprotective properties. |
| AID1587930 | Inhibition of LPS/IFNgamma-stimulated lipid peroxidation in mouse RAW264.7 cells at 5 uM after 24 hrs by BODIPY 581/591 C11-staining based FACS assay | 2019 | Journal of medicinal chemistry, 05-09, Volume: 62, Issue:9 | Novel 15-Lipoxygenase-1 Inhibitor Protects Macrophages from Lipopolysaccharide-Induced Cytotoxicity. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 2 (33.33) | 29.6817 |
| 2010's | 4 (66.67) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (17.97) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 6 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||