3,3,5-trimethylcyclohexanol : A secondary alcohol that is cyclohexanol substituted by two methyl groups at the 3-position and one methyl group at the 5-position. It exhibits inhibitory activity against HMG-CoA reductase ( EC 1.1.1.34/EC 1.1.1.88). [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 | 8298 |
| CHEMBL ID | 3186608 |
| CHEBI ID | 59065 |
| SCHEMBL ID | 113337 |
| MeSH ID | M0112905 |
| Synonym |
|---|
| dihydroisophorol |
| CHEBI:59065 , |
| STK709217 |
| EN300-18641 |
| cyclohexanol,3,5-trimethyl- |
| 3,5-trimethyl-1-cyclohexanol |
| nsc-4008 |
| 116-02-9 |
| wln: l6tj a1 a1 cq e1 |
| nsc4008 |
| homomenthol |
| 3,5-trimethylcyclohexanol |
| isophorol, dihydro- |
| cyclonol |
| 3,3,5-trimethylcyclohexanol |
| trans-3,3,5-trimethylcyclohexanol |
| brn 2203314 |
| ai3-01646 |
| hsdb 2039 |
| einecs 204-122-7 |
| 3,5,5-trimethylcyclohexanol |
| 1-methyl-3-dimethylcyclohexanol-5 |
| nsc 4008 |
| 3,3,5-trimethyl-1-cyclohexanol |
| cyclohexanol, 3,3,5-trimethyl- |
| NCGC00160581-01 |
| T2693 |
| AKOS000249479 |
| 3,3,5-trimethylcyclohexan-1-ol |
| T0472 |
| 767-54-4 |
| 3,3,5-trimethyl-cyclohexan-1-ol |
| NCGC00255548-01 |
| dtxcid7021815 |
| dtxsid9041815 , |
| tox21_301500 |
| cas-116-02-9 |
| tox21_111915 |
| einecs 212-183-6 |
| trans-3,5,5-trimethylcyclohexan-1-ol |
| unii-08cl3g94gh |
| 08cl3g94gh , |
| 3-06-00-00115 (beilstein handbook reference) |
| FT-0614015 |
| FT-0623905 |
| FT-0614016 |
| 3,3,5-trimethylcyclohexanol [fhfi] |
| 3,3,5-trimethylcyclohexanol [hsdb] |
| SCHEMBL113337 |
| BBL027854 |
| 3,3,5-trimethyl-cyclohexanol |
| AKOS016844021 |
| W-108586 |
| CHEMBL3186608 |
| F8889-6309 |
| mfcd00019378 |
| 3,3,5-trimethyl-(1r,5s)-rel-cyclohexanol |
| fema 3962 |
| 3,3,5-trimethylcyclohexanol,camp t |
| 3,3,5-trimethylcyclohexanol (c,t) |
| dihydro-isophorol |
| 3,3,5-trimethyl-trans-cyclohexanol |
| 3,3,5-trimethyl-cis-cyclohexanol |
| 3,3,5-trimethyl cyclohexanol |
| Q27126431 |
| AS-15521 |
| cis-3,3,5-trimethylcyclohexanol (contains ca. 6 % trans- isomer) |
| BCP30903 |
| cyclonol;homomenthol;1-methyl-3-dimethylcyclohexanol-5; 3,3,5-trimethyl; 3,3,5-trimethyl-cyclohexano |
| D92347 |
| A893661 |
| 3,3,5-trimethyl-1-cyclohexanol; cyclonol |
| STARBLD0021733 |
| SB83862 |
| CS-0152689 |
| 611-02-9 |
| rac-(1r,5s)-3,3,5-trimethylcyclohexan-1-ol, trans |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The bioavailability of five capsules of cyclandelate that are commercially available in Japan was determined in ten healthy volunteers by measuring mandelic acid (a main metabolite of cyclandelate) excreted in the urine." | ( Effect of food on the bioavailability of cyclandelate from commercial capsules. Aoyagi, N; Ejima, A; Imazato, Y; Kaniwa, N; Ogata, H; Takahashi, T; Uezono, Y, 1991) | 0.28 |
| "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 |
| Excerpt | Relevance | Reference |
|---|---|---|
| "Oral dosing of rats with cyclohexanol and methylcyclohexanols resulted in the inhibition of hepatic HMGCoA reductase." | ( Cyclohexanol and methylcyclohexanols. A family of inhibitors of hepatic HMGCoA reductase in vivo. Miciak, A; Middleton, B; White, DA, 1986) | 0.27 |
| " There was no change, neither elevation nor depression, of the amount of microsomal membrane components cytochromes b5 and P-450, not was the activity of another microsomal enzyme, arylesterase, affected by dosing with cyclandelate or trimethylcyclohexanol." | ( The inhibition of hepatic S-3-hydroxy-3-methylglutaryl-CoA reductase by 3,3,5-trimethylcyclohexanol and its mandelic acid ester, cyclandelate. Bell, GD; Miciak, A; Middleton, A; Middleton, B; White, DA, 1983) | 0.5 |
| " In both acute and long-term dosing experiments TMC significantly inhibited hepatic S-3-hydroxy-3-methylglutaryl coenzyme A (HMGCoA) reductase." | ( The effects of 3,5,5-trimethylcyclohexanol on hepatic cholesterol synthesis, bile flow and biliary lipid secretion in the rat. Bell, GD; Clegg, RJ; Ellis, WR; Middleton, B; White, DA, 1984) | 0.27 |
| Role | Description |
|---|---|
| EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor | Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme. |
| [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 |
|---|---|
| cyclohexanols | An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton. |
| secondary alcohol | A secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it. |
| [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) |
|---|---|---|---|---|---|---|---|
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 54.4827 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 54.9410 | 0.3758 | 27.4851 | 61.6524 | AID743220 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID504749 | qHTS profiling for inhibitors of Plasmodium falciparum proliferation | 2011 | Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043 | Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets. |
| 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. |
| 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. |
| 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. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 5 (50.00) | 18.7374 |
| 1990's | 1 (10.00) | 18.2507 |
| 2000's | 0 (0.00) | 29.6817 |
| 2010's | 3 (30.00) | 24.3611 |
| 2020's | 1 (10.00) | 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 (23.39) 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 | 10 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||