Page last updated: 2024-08-05 10:33:26
catechols
Any compound containing an o-diphenol component.
ChEBI ID: 33566
Members (84)
| Member | Definition | Role |
|---|---|---|
| 1-(3,4-dihydroxyphenyl)-2-thiocyanate-ethanone | A member of the class of thiocyanates that is 3,4-dihydroxyacetophenone in which one of the methyl hydrogens has been replaced by the sulfur of a cyanosulfanediyl (-SC#N) group. It has been found to induce the expression of the endoplasmic reticulum chaperone protein GRP78 (78 kDa glucose-regulated protein, BiP, a highly conserved member of the 70 kDa heat shock protein family) leading to an attenuation of the unfolded protein response. It protects neuronal cells and retinal cells from endoplasmic reticulum (ER)-stress induced cell death. | 2-(3,4-dihydroxyphenyl)-2-oxoethyl thiocyanate |
| 11-hydroxysugiol | An abietane diterpenoid that is sugiol in which the hydrogen ortho to the phenolic hydroxy group has been replaced by a hydroxy group. | 11-hydroxysugiol |
| 2-hydroxyestrone | A 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2. | 2-hydroxyestrone |
| 2-s-cysteinyldopa | An L-tyrosine derivative that is L-DOPA in which the hydrogen at position 2 on the phenyl ring is replaced by a cysteinyl group. Found in the urine of patients with melanoma. | 2-S-cysteinyl-DOPA |
| 2,3-dihydroxybiphenyl | A member of the class of hydroxybiphenyls that is 1,1'-biphenyl substituted by hydroxy groups at positions 2 and 3. | biphenyl-2,3-diol |
| 2',3,4-trihydroxychalcone | A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2', 3 and 4. The precursor of 3',4'-dihydroxyaurone. | 2',3,4-trihydroxy-trans-chalcone |
| 3-heptadecylcatechol | Catechol substituted at position 3 with a heptadecyl group. | 3-heptadecylcatechol |
| 3-hydroxyterphenyllin | A para-terphenyl that is the 3-hydroxy derivative of terphenyllin. It has been isolated from Aspergillus taichungensis. | 3-hydroxyterphenyllin |
| 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A member of the class of catechols that is catechol in which a hydrogen that is ortho to one of the hydroxy groups has been replaced by a methoxy group.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). | 3-methoxycatechol |
| 3-o-methylgallic acid | A member of the class of benzoic acids that is gallic acid in which the phenolic hydroxy group at position 3 is converted into the corresponding methyl ether. | 3-O-methylgallic acid |
| 3-pentadecacatechol | Catechol substituted at position 3 with a pentadecyl group. | 3-pentadecylcatechol |
| 3,3',4,5'-tetrahydroxystilbene | A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5. | piceatannol |
| 3,4-dihydroxyacetophenone | A dihydroxyacetophenone that is acetophenone carrying hydroxy groups at positions 3' and 4'. | 3,4-dihydroxyacetophenone; 3',4'-dihydroxyacetophenone |
| 3,4-dihydroxybenzylamine | 3,4-dihydroxybenzylamine | |
| 3,4-dihydroxymandelic acid | A catechol that is the 3,4-dihydroxy derivative of mandelic acid; a metabolite of L-dopa. | 3,4-dihydroxymandelic acid |
| 3,4-dihydroxyphenylacetaldehyde | A phenylacetaldehyde in which the 3 and 4 positions of the phenyl group are substituted by hydroxy groups. | 3,4-dihydroxyphenylacetaldehyde |
| 3,4-dihydroxyphenylacetic acid | A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine. | (3,4-dihydroxyphenyl)acetic acid |
| 3,4-dihydroxyphenylethanol | A member of the class of catechols that is benzene-1,2-diol substituted by a 2-hydroxyethyl group at position 4. Isolated from Olea europaea, it exhibits antioxidant and antineoplastic activities. | hydroxytyrosol |
| 3,4-dihydroxyphenylglycol | A tetrol composed of ethyleneglycol having a 3,4-dihydroxyphenyl group at the 1-position. | 3,4-dihydroxyphenylethyleneglycol |
| 3,4-dihydroxyphenylglycolaldehyde | A hydroxyaldehyde consisting of phenylacetaldehyde having three hydroxy substituents located at the alpha-, 3- and 4-positions. It is a metabolite of noradrenaline. | 3,4-dihydroxymandelaldehyde |
| 3,4-dihydroxyphenyllactic acid | 3-(3,4-dihydroxyphenyl)lactic acid | |
| 3',4'-dihydroxyaurone | A hydroxyaurone that is aurone which is substituted by hydroxy groups at the 3' and 4' positions; major species at pH 7.3. It shows inhibitory activity against several isoforms of the histone deacetylase complex (HDAC). | 3',4'-dihydroxyaurone |
| 4-[(1S)-1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol | 4-[(1S)-1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol | |
| 4-bromocatechol | 4-Bromocatechol | |
| 4-ethylcatechol | 4-Ethyl-1,2-benzenediol | |
| 4-fluorocatechol | 4-Fluorocatechol | |
| 4-hydroxyestrone | A 4-hydroxy steroid that is estrone substituted by a hydroxy group at position 4. | 4-hydroxyestrone |
| 4-nitrocatechol | A member of the class of catechols that is benzene-1,2-diol substituted by a nitro group at position 4.It is the by-product of the hydroxylation of p-nitrophenol. | 4-nitrocatechol |
| 5-o-caffeoylshikimic acid | A carboxylic ester obtained by formal condensation of the carboxy group of (E)-caffeic acid with the 5-hydroxy group of shikimic acid. | 5-[(E)-caffeoyl]shikimic acid |
| 6-fluoronorepinephrine | 4-(2-amino-1-hydroxyethyl)-5-fluorobenzene-1,2-diol | |
| a 3253 | 4-Aminocatechol | |
| a 77636 | An isochromene that is 3,4-dihydroisochromene-5,6-diol bearing additional aminomethyl and 1-adamantyl substituents at positions 1 and 3 respectively (the 1R,3S-diastereomer). Potent and selective dopamine D1-like receptor agonist (pEC50 values are 8.97 and < 5 for D1-like and D2-like receptors respectively). Displays anti-Parkinsonian activity following oral administration in vivo. | (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol |
| acteoside | A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid. | acteoside |
| ag-490 | A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2E)-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoic acid with the amino group of benzylamine. | tyrphostin B42 |
| altenusin | A carboxybiphenyl that is [biphenyl]-2-carboxylic acid which is substituted by a hydroxy group at positions 3, 4' and 5', methoxy group at position 5 and a methyl group at position 2'. It is a a metabolite isolated from Alternaria and several other fungal species. | altenusin |
| arachidonyl dopamine | Arachidonoyl dopamine | |
| aspalathin | A member of the class of dihydrochalcones that is the 2-C-beta-D-glucopyranide of phloroglucinol and which is substituted at position 4 by a 3-(3,4-dihydroxyphenyl)propanoyl group. A metabolite of red bush, Aspalathus linearis (and present in the herbal tea made from the leaves), aspalathin exhibits significant hypoglycemic activity. | aspalathin |
| benserazide | A carbohydrazide that results from the formal condensation of the carboxy group of DL-serine with the primary amino group of 4-(hydrazinylmethyl)benzene-1,2,3-triol. An aromatic-L-amino-acid decarboxylase inhibitor (DOPA decarboxylase inhibitor) that does not enter the central nervous system, it is used as its hydrochloride salt as an adjunct to levodopa in the treatment of parkinsonism. By preventing the conversion of levodopa to dopamine in the periphery, it causes an increase in the amount of levodopa reaching the central nervous system and so reduces the required dose. Benserazide has no antiparkinson actions when given alone. | benserazide |
| beta-lipotropin, gln(9)- | A crown compound that is enterobactin in which the pro-R hydrogens at positions 2, 6 and 10 of the trilactone backbone are replaced by methyl groups, and in which a glycine spacer separates the trilactone backbone from each of the catecholamide arms. It is the endogenous siderophore of Bacillus subtilis, used for the acquisition of iron. | corynebactin |
| brazilin | A organic heterotetracyclic compound that is a red pigment obtained from the wood of Caesalpinia echinata (Brazil-wood) or Caesalpinia sappan (sappan-wood). | brazilin |
| caffeic acid | A hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. | caffeic acid |
| capsazepine | A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist. | capsazepine |
| carbidopa | 3-(3,4-Dihydroxyphenyl)propanoic acid in which the hydrogens alpha- to the carboxyl group are substituted by hydrazinyl and methyl groups (S-configuration). Carbidopa is a dopa decarboxylase inhibitor, so prevents conversion of levodopa to dopamine. It has no antiparkinson activity by itself, but is used (commonly as its hydrate) in the management of Parkinson's disease to reduce peripheral adverse effects of levodopa. | carbidopa (anhydrous) |
| carbidopa | The hydrate of 3-(3,4-dihydroxyphenyl)propanoic acid in which the hydrogens alpha- to the carboxyl group are substituted by hydrazinyl and methyl groups (S-configuration). Carbidopa is a dopa decarboxylase inhibitor, so prevents conversion of levodopa to dopamine. It has no antiparkinson activity by itself, but is used in the management of Parkinson's disease to reduce peripheral adverse effects of levodopa. | carbidopa |
| catechol | A benzenediol comprising of a benzene core carrying two hydroxy substituents ortho to each other. | catechol |
| chrysobactin | A catechol-type siderophore with a structure of D-lysyl-L-serine substituted on N(2) of the lysyl residue by a 2,3-dihydroxybenzoyl group. It is produced by the Gram-negative bacillus Dickeya dadantii (previously known as Erwinia chrysanthem). Only the catecholate hydroxyl groups participate in metal coordination, so chrysobactin cannot provide full 1:1 coordination of Fe(III); at neutral pH and concentrations of about 0.1 mM, ferric chrysobactin exists as a mixture of bis and tris complexes. | chrysobactin |
| colterol | A member of the class of ethanolamines that is catechol in which the hydrogen at position 4 is replaced by a 2-(tert-butylamino)-1-hydroxyethyl group. | colterol |
| dihydro-n-caffeoyltyramine | 3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]propanimidic acid | |
| droxidopa | A serine derivative that is L-serine substituted at the beta-position by a 3,4-dihydroxyphenyl group. A prodrug for noradrenalone, it is used for treatment of neurogenic orthostatic hypotension | droxidopa |
| ellagic acid | An organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates. | ellagic acid |
| entacapone | A monocarboxylic acid amide that is N,N-diethylprop-2-enamide in which the hydrogen at position 2 is substituted by a cyano group and the hydrogen at the 3E position is substituted by a 3,4-dihydroxy-5-nitrophenyl group. | entacapone |
| enterobactin | A macrotriolide produced by certain members of Enterobacteriaceae, e.g. Escherichia coli and Salmonella. | enterobactin |
| ethyl protocatechuate | An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa. | ethyl 3,4-dihydroxybenzoate |
| ethylnorepinephrine | ethylnorepinephrine | |
| hispidin | Fungal metabolite first found in basidiomycete Inonotus hispidus (formerly Polyporus hispidus). | hispidin |
| isoproterenol | A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders. | isoprenaline |
| isoproterenol hydrochloride | DL-Isoprenaline hydrochloride | |
| lanosol | Lanosol | |
| masoprocol | A tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups. Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor. | nordihydroguaiaretic acid |
| methyl 3,4-dihydroxybenzoate | A methyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with methanol. | methyl 3,4-dihydroxybenzoate |
| myxochelin b | A member of the class of benzamides obtained by formal condensation of the 1- and 6-amino groups of hexane-1,2,6-triamine with the carboxy groups from two molecules of 2,3-dihydroxybenzoic acid followed by reduction of the amide carbonyl at position 5 to a hydroxy group. | myxochelin B |
| n-acetyldopamine | A secondary carboxamide obtained by formal condensation of the carboxy group of acetic acid with the amino group of dopamine. A dopamine metabolite. | N-acetyldopamine |
| n-caffeoyltyramine | N-cis-Caffeoyltyramine | |
| n-oleoyldopamine | A fatty amide resulting from the formal condensation of the carboxy group of oleic acid with the amino group of dopamine. Synthesised in catecholaminergic neurons, it crosses the blood-brain barrier and might be considered as a carrier of dopamine into the brain. It is a transient receptor potential vanilloid type 1 (TRPV1) receptor agonist. | N-oleoyldopamine |
| n'-(3,4-dihydroxybenzylidene)-3-hydroxy-2-naphthahydrazide | A carbohydrazide resulting from the formal condensation of the hydrazone moiety of 3,4-dihydroxybenzaldehyde hydrazone with the carboxy group of 3-hydroxy-2-naphthoic acid. It is a cell-permeable, reversible noncompetitive inhibitor of the GTPase activity of dynamin 1 and 2 and Drp1 (mitochondrial), while exhibiting no significant effect against two other small GTPases, MxA and Cdc42. | dynasore |
| n(beta)-alanyldopamine | 3-amino-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide | |
| norbelladine | A phenethylamine alkaloid that is tyramine in which one of the amino hydrogens has been replaced by a 3,4-dihydroxybenzyl group. | norbelladine |
| oleuropein | A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars. | oleuropein |
| oleuropein aglycone | A secoiridoid that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2R,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars. | oleuropein aglycone |
| protocatechuic acid | A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. | 3,4-dihydroxybenzoic acid |
| protosappanin a | protosappanin A | |
| rimiterol | rimiterol | |
| salvianolic acid B | A member of the class of 1-benzofurans that is an antioxidant and free radical scavenging compound extracted from S. miltiorrhiza | salvianolic acid B |
| salvin | An abietane diterpenoid that is abieta-8,11,13-triene substituted by hydroxy groups at positions 11 and 12 and a carboxy group at position 20. It is isolated from rosemary (Rosmarinus officinalis) and common sage (Salvia officinalis) and exhibits anti-angiogenic, antineoplastic, antioxidant and anti-HIV activity. | carnosic acid |
| sappanchalcone | A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy groups at positions 3, 4 and 4' and a methoxy group at position 2'. Isolated from Caesalpinia sappan, it exhibits neuroprotective and cytoprotective activity. | sappanchalcone |
| sk&f 77434 | A benzazepine that is 2,3,4,5-tetrahydro-3-benzazepine bearing a phenyl substituent at position 1, an allyl substituent at position 3 and two hydroxy substituents at positions 7 and 8. Selective dopamine D1-like receptor partial agonist (IC50 values are 19.7 and 2425 nM for binding to D1-like and D2-like receptors respectively). Centrally active following systemic administration in vivo. | N-allyl-1-phenyl-2,3,4,5-tetrahydro-3-benzazepine-7,8-diol |
| sk&f 83959 | A benzazepine that is 2,3,4,5-tetrahydro-3-benzazepine bearing a 3-methylphenyl substituent at position 1, a methyl substituent at position 3, a chloro substituent at position 6 and two hydroxy substituents at positions 7 and 8. Dopamine D1-like receptor partial agonist (Ki values are 1.18, 7.56, 920 and 399 nM for rat D1, D5, D2 and D3 receptors respectively). May act as an antagonist in vivo, producing anti-Parkinsonian effects and antagonising the behavioral effects of cocaine. | N-methyl-6-chloro-1-(3-methylphenyl)-2,3,4,5-tetrahydro-3-benzazepine-7,8-diol |
| sk&f-38393 | A benzazepine that is 2,3,4,5-tetrahydro-3-benzazepine bearing a phenyl substituent at position 1 and two hydroxy substituents at positions 7 and 8. | 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol |
| tetrahydroxycurcumin | A beta-diketone that is curcumin in which the two methoxy groups have been replaced by hydroxy groups. It is a metabolite of curcumin. | tetrahydroxycurcumin |
| thunberginol f | An isobenzofuranone that is 2-benzofuran-1(3H)-one substituted by a hydroxy group at position 7 and a 3,4-dihydroxybenzylidene group at position 3. It has been isolated from the roots of Scorzonera judaica. | thunberginol F |
| tolcapone | Benzophenone substituted on one of the phenyl rings at C-3 and C-4 by hydroxy groups and at C-5 by a nitro group, and on the other phenyl ring by a methyl group at C-4. It is an inhibitor of catechol O-methyltransferase. | tolcapone |
| tyrphostin a23 | 2-[(3,4-dihydroxyphenyl)methylidene]propanedinitrile | |
| vanchrobactin | A catechol-type natural product that is composed of 2,3-dihydroxybenzoic acid, D-arginine and L-serine joined in sequence by peptide linkages. It is a siderophore synthesized by the bacterial fish pathogen Vibrio anguillarum. | vanchrobactin |
| violaceol II | An aromatic ether in which the ether functionality links a 2,3-dihydroxy-5-methylphenyl group with a 2,6-dihydroxy-4-methylphenyl group. Fungal metabolite isolated inter alia from Aspergillus spp. | violaceol II |
Research
Studies (50,382)
| Timeframe | Studies, Drugs in This Class (%) | All Drugs % |
|---|---|---|
| pre-1990 | 20,889 (41.46) | 18.7374 |
| 1990's | 10,440 (20.72) | 18.2507 |
| 2000's | 8,109 (16.10) | 29.6817 |
| 2010's | 8,406 (16.68) | 24.3611 |
| 2020's | 2,538 (5.04) | 2.80 |
Study Types
| Publication Type | Studies, Drugs in This Class (%) | All Drugs (%) |
|---|---|---|
| Trials | 1,483 (2.74%) | 5.53% |
| Reviews | 1,314 (2.43%) | 6.00% |
| Case Studies | 608 (1.12%) | 4.05% |
| Observational | 19 (0.04%) | 0.25% |
| Other | 50,725 (93.68%) | 84.16% |