CHIC-35 : An organic heterotricyclic compound resulting from the formal fusion of the 2-3 bond of 5-chloroindole with the 2-3 bond of cycloheptanecarboxamide (the S enantiomer). It is a potent, cell-permeable, metabolically stable and selective inhibitor of the deacetylase SIRT1. [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 | 914268 |
| CHEMBL ID | 198609 |
| CHEBI ID | 142489 |
| SCHEMBL ID | 8257650 |
| Synonym |
|---|
| CHEMBL198609 , |
| bdbm50178775 |
| (s)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide |
| (s)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxylic acid amide |
| chic-35 |
| CHEBI:142489 |
| compound (s)-35 |
| sirt1 inhibitor iv, (s)-35 |
| (6s)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide |
| 848193-72-6 |
| SCHEMBL8257650 |
| chic-35, >=97% (chiral, hplc) |
| DTXSID40358759 |
| NCGC00485645-01 |
| chic35 |
| sirt1 inhibitor iv, (s)-35 - cas 848193-72-6 |
| Q27454741 |
| (6s)-2-chloro-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-6-carboxamide |
| (s)-2-chloro-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-6-carboxamide |
| HY-111303 |
| CS-0034887 |
| PD015708 |
| AKOS040748127 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
| Role | Description |
|---|---|
| EC 3.5.1.98 (histone deacetylase) inhibitor | An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98). |
| [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 |
|---|---|
| aromatic compound | A cyclically conjugated molecular entity with a stability (due to delocalization) significantly greater than that of a hypothetical localized structure (e.g. Kekule structure) is said to possess aromatic character. |
| organic heterotricyclic compound | An organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms. |
| organochlorine compound | An organochlorine compound is a compound containing at least one carbon-chlorine bond. |
| primary carboxamide | A carboxamide resulting from the formal condensation of a carboxylic acid with ammonia; formula RC(=O)NH2. |
| [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 | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| NAD-dependent protein deacetylase sirtuin-1 | Homo sapiens (human) | IC50 (µMol) | 0.0630 | 0.0060 | 1.6250 | 9.0000 | AID256743 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1347159 | Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1347160 | Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID320398 | Induction of tubulin hyperacetylation in human MCF7 cells at 10 uM by Western blot | 2008 | Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5 | Structure-activity studies on splitomicin derivatives as sirtuin inhibitors and computational prediction of binding mode. |
| AID256743 | Inhibitory activity against recombinant human SIRT1 expressed in Escherichia coli by fluorimetric assay | 2005 | Journal of medicinal chemistry, Dec-15, Volume: 48, Issue:25 | Discovery of indoles as potent and selective inhibitors of the deacetylase SIRT1. |
| [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 (40.00) | 29.6817 |
| 2010's | 1 (20.00) | 24.3611 |
| 2020's | 2 (40.00) | 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 strong demand-to-supply ratio for research on this compound.
| This Compound (35.35) 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 | 5 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||