Page last updated: 2024-12-05
3-methoxycatechol
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
3-Methoxycatechol, also known as guaiacol, is a naturally occurring organic compound found in various plants and foods. It is a colorless or pale yellow liquid with a characteristic smoky, medicinal odor. Guaiacol is used in the synthesis of various pharmaceuticals, including guaifenesin (an expectorant) and guaiacol glyceryl ether (a topical analgesic). It exhibits antioxidant and anti-inflammatory properties, and has been studied for its potential therapeutic effects in various conditions, such as respiratory diseases, cancer, and cardiovascular disease. The compound is also used as a flavoring agent in food and beverages. Its importance lies in its versatility and diverse applications in medicine, food, and other industries.'
3-methoxycatechol : A member of the class of catechols that is catechol in which a hydrogen that is ortho to one of the hydroxy groups has been replaced by a methoxy group. It displays agonistic activity against G protein-coupled receptor 35 (GPR35). [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]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 13622 |
| CHEMBL ID | 1518159 |
| CHEBI ID | 141700 |
| SCHEMBL ID | 67332 |
| MeSH ID | M0182085 |
Synonyms (74)
| Synonym |
|---|
| 3-methoxy-benzene-1,2-diol |
| DIVK1C_007017 |
| SDCCGMLS-0066910.P001 |
| 3-(methyloxy)benzene-1,2-diol |
| einecs 213-276-4 |
| ccris 7577 |
| ai3-21349 |
| 6-methoxycatechol |
| nsc 66525 |
| pyrogallol 1-monomethyl ether |
| pyrogallol 1-methyl ether |
| 934-00-9 |
| pyrocatechol, 3-methoxy- |
| 3-methoxypyrocatechol |
| nsc66525 |
| 3-methoxycatechol |
| 1,2-dihydroxy-3-methoxybenzene |
| 2,3-dihydroxyanisole |
| 3-methoxy-1,2-benzenediol |
| nsc-66525 |
| SPECTRUM4_001656 |
| SPECTRUM_001637 |
| 3-methoxybenzene-1,2-diol |
| 1,2-benzenediol, 3-methoxy- |
| BSPBIO_002821 |
| inchi=1/c7h8o3/c1-10-6-4-2-3-5(8)7(6)9/h2-4,8-9h,1h |
| 3-methoxycatechol, 99% |
| SPECTRUM5_000531 |
| NCGC00095761-01 |
| KBIOSS_002117 |
| KBIO2_004685 |
| KBIO1_001961 |
| KBIO2_002117 |
| KBIOGR_002151 |
| KBIO2_007253 |
| KBIO3_002321 |
| SPECTRUM2_001917 |
| SPBIO_001914 |
| SPECPLUS_000921 |
| SPECTRUM3_001181 |
| SPECTRUM1600919 |
| NCGC00095761-02 |
| M0524 |
| 3-methoxy-o-hydroquinone |
| 1-o-methylpyrogallol |
| CHEBI:141700 |
| AKOS000121420 |
| A844580 |
| NCGC00095761-03 |
| ic13u5393c , |
| unii-ic13u5393c |
| tox21_200504 |
| cas-934-00-9 |
| dtxsid4020826 , |
| dtxcid00826 |
| NCGC00258058-01 |
| CCG-38485 |
| BP-20353 |
| FT-0616000 |
| CHEMBL1518159 |
| SCHEMBL67332 |
| 1,2-benzenediol,3-methoxy- |
| mfcd00002191 |
| SR-05000002377-1 |
| sr-05000002377 |
| F0001-2249 |
| F30220 |
| AS-48298 |
| BRD-K97139501-001-03-3 |
| Q27280656 |
| CS-0179150 |
| EN300-21179 |
| PD000449 |
| SY048938 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Roles (1)
| Role | Description |
|---|---|
| G-protein-coupled receptor agonist | An agonist that binds to and activates G-protein-coupled receptors |
| [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] | |
Drug Classes (2)
| Class | Description |
|---|---|
| catechols | Any compound containing an o-diphenol component. |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| [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 Targets (63)
Potency Measurements
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE | Homo sapiens (human) | Potency | 2.5119 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
| Chain A, Putative fructose-1,6-bisphosphate aldolase | Giardia intestinalis | Potency | 17.7407 | 0.1409 | 11.1940 | 39.8107 | AID2451 |
| Chain A, HADH2 protein | Homo sapiens (human) | Potency | 3.1623 | 0.0251 | 20.2376 | 39.8107 | AID893 |
| Chain B, HADH2 protein | Homo sapiens (human) | Potency | 3.1623 | 0.0251 | 20.2376 | 39.8107 | AID893 |
| Chain A, 2-oxoglutarate Oxygenase | Homo sapiens (human) | Potency | 7.9433 | 0.1778 | 14.3909 | 39.8107 | AID2147 |
| 15-lipoxygenase, partial | Homo sapiens (human) | Potency | 0.7943 | 0.0126 | 10.6917 | 88.5700 | AID887 |
| phosphopantetheinyl transferase | Bacillus subtilis | Potency | 19.9526 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 60.0476 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
| TDP1 protein | Homo sapiens (human) | Potency | 4.1367 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 30.8038 | 0.0007 | 14.5928 | 83.7951 | AID1259368; AID1259369; AID1259392 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 19.6221 | 0.1800 | 13.5574 | 39.8107 | AID1460; AID1468 |
| AR protein | Homo sapiens (human) | Potency | 30.9091 | 0.0002 | 21.2231 | 8,912.5098 | AID743035; AID743036; AID743042; AID743053; AID743063 |
| aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 1.0156 | 0.0112 | 12.4002 | 100.0000 | AID1030; AID493210 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 23.2677 | 0.0006 | 57.9133 | 22,387.1992 | AID1259377; AID1259378; AID1259394 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 63.9218 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224893 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 65.4951 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553; AID1159555 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 53.9177 | 0.0008 | 17.5051 | 59.3239 | AID1159531 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 39.1242 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 50.9016 | 0.3758 | 27.4851 | 61.6524 | AID743217 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 25.2800 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 31.1213 | 0.0002 | 29.3054 | 16,493.5996 | AID743069; AID743075; AID743077; AID743078 |
| 67.9K protein | Vaccinia virus | Potency | 11.2202 | 0.0001 | 8.4406 | 100.0000 | AID720580 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 20.8647 | 0.0010 | 19.4141 | 70.9645 | AID743094; AID743140; AID743191 |
| aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 35.9459 | 0.0007 | 23.0674 | 1,258.9301 | AID743085; AID743122 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 35.7089 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| activating transcription factor 6 | Homo sapiens (human) | Potency | 57.1125 | 0.1434 | 27.6121 | 59.8106 | AID1159516 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 44.0972 | 0.0578 | 21.1097 | 61.2679 | AID1159526; AID1159528 |
| Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 95.5763 | 0.0391 | 47.5451 | 146.8240 | AID1224845; AID1224896 |
| cellular tumor antigen p53 isoform a | Homo sapiens (human) | Potency | 5.6607 | 0.3162 | 12.4435 | 31.6228 | AID902; AID924 |
| polyunsaturated fatty acid lipoxygenase ALOX12 | Homo sapiens (human) | Potency | 39.8107 | 1.0000 | 12.2326 | 31.6228 | AID1452 |
| 15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1 | Homo sapiens (human) | Potency | 15.8489 | 0.0018 | 15.6638 | 39.8107 | AID894 |
| vitamin D3 receptor isoform VDRA | Homo sapiens (human) | Potency | 50.1187 | 0.3548 | 28.0659 | 89.1251 | AID504847 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 40.0145 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| heat shock protein beta-1 | Homo sapiens (human) | Potency | 52.1267 | 0.0420 | 27.3789 | 61.6448 | AID743210; AID743228 |
| mitogen-activated protein kinase 1 | Homo sapiens (human) | Potency | 17.7828 | 0.0398 | 16.7842 | 39.8107 | AID1454 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 3.0453 | 0.0006 | 27.2152 | 1,122.0200 | AID743202; AID743219 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 23.3507 | 0.0079 | 8.2332 | 1,122.0200 | AID2546; AID2551 |
| DNA polymerase kappa isoform 1 | Homo sapiens (human) | Potency | 3.1623 | 0.0316 | 22.3146 | 100.0000 | AID588579 |
| cytochrome P450 3A4 isoform 1 | Homo sapiens (human) | Potency | 19.9526 | 0.0316 | 10.2792 | 39.8107 | AID884; AID885 |
| lamin isoform A-delta10 | Homo sapiens (human) | Potency | 3.1623 | 0.8913 | 12.0676 | 28.1838 | AID1487 |
| Gamma-aminobutyric acid receptor subunit pi | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Polyunsaturated fatty acid lipoxygenase ALOX15B | Homo sapiens (human) | Potency | 1.2589 | 0.3162 | 12.7657 | 31.6228 | AID881 |
| Integrin beta-3 | Homo sapiens (human) | Potency | 5.0119 | 0.3162 | 11.4157 | 31.6228 | AID924 |
| Integrin alpha-IIb | Homo sapiens (human) | Potency | 5.0119 | 0.3162 | 11.4157 | 31.6228 | AID924 |
| Gamma-aminobutyric acid receptor subunit beta-1 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit delta | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-2 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-5 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-3 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-1 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-2 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-4 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-3 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-6 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Histamine H2 receptor | Cavia porcellus (domestic guinea pig) | Potency | 1.2589 | 0.0063 | 8.2350 | 39.8107 | AID881 |
| Gamma-aminobutyric acid receptor subunit alpha-1 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-3 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-2 | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Inositol monophosphatase 1 | Rattus norvegicus (Norway rat) | Potency | 10.0000 | 1.0000 | 10.4756 | 28.1838 | AID1457 |
| GABA theta subunit | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| ATPase family AAA domain-containing protein 5 | Homo sapiens (human) | Potency | 57.7018 | 0.0119 | 17.9420 | 71.5630 | AID651632; AID720516 |
| Ataxin-2 | Homo sapiens (human) | Potency | 56.5948 | 0.0119 | 12.2221 | 68.7989 | AID651632 |
| Gamma-aminobutyric acid receptor subunit epsilon | Rattus norvegicus (Norway rat) | Potency | 19.9526 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (109)
Molecular Functions (35)
Ceullar Components (41)
Bioassays (7)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1159550 | Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening | 2015 | Nature cell biology, Nov, Volume: 17, Issue:11 | 6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling. |
| AID977602 | Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6 | Structure-based identification of OATP1B1/3 inhibitors. |
| AID1335038 | Cytotoxicity against human MCF7 cells assessed as cell growth inhibition after 48 hrs by SRB assay | 2017 | Bioorganic & medicinal chemistry, 02-01, Volume: 25, Issue:3 | A one-pot laccase-catalysed synthesis of coumestan derivatives and their anticancer activity. |
| AID1335036 | Cytotoxicity against human TK10 cells assessed as cell growth inhibition after 48 hrs by SRB assay | 2017 | Bioorganic & medicinal chemistry, 02-01, Volume: 25, Issue:3 | A one-pot laccase-catalysed synthesis of coumestan derivatives and their anticancer activity. |
| AID1335037 | Cytotoxicity against human UACC62 cells assessed as cell growth inhibition after 48 hrs by SRB assay | 2017 | Bioorganic & medicinal chemistry, 02-01, Volume: 25, Issue:3 | A one-pot laccase-catalysed synthesis of coumestan derivatives and their anticancer activity. |
| AID977599 | Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6 | Structure-based identification of OATP1B1/3 inhibitors. |
| AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal of biomolecular screening, Jul, Volume: 21, Issue:6 | A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (11)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 3 (27.27) | 18.2507 |
| 2000's | 2 (18.18) | 29.6817 |
| 2010's | 5 (45.45) | 24.3611 |
| 2020's | 1 (9.09) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 25.69
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 (25.69) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (9.09%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 10 (90.91%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||