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catechols

Any compound containing an o-diphenol component.

ChEBI ID: 33566

Members (84)

MemberDefinitionRole
1-(3,4-dihydroxyphenyl)-2-thiocyanate-ethanoneA member of the class of thiocyanates that is 3,4-dihydroxyacetophenone in which one of the methyl hydrogens has been replaced by the sulfur of a cyanosulfanediyl (-SC#N) group.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11-hydroxysugiolAn abietane diterpenoid that is sugiol in which the hydrogen ortho to the phenolic hydroxy group has been replaced by a hydroxy group.11-hydroxysugiol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-hydroxyestroneA 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2.2-hydroxyestrone
2-s-cysteinyldopaAn 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-dihydroxybiphenylA 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-trihydroxychalconeA 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-heptadecylcatecholCatechol substituted at position 3 with a heptadecyl group.3-heptadecylcatechol
3-hydroxyterphenyllinA para-terphenyl that is the 3-hydroxy derivative of terphenyllin. It has been isolated from Aspergillus taichungensis.3-hydroxyterphenyllin
3-methoxycatecholA member of the class of catechols that is catechol in which a hydrogen that is ortho to one of the hydroxy groups has been replaced by a methoxy group.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 acidA 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-pentadecacatecholCatechol substituted at position 3 with a pentadecyl group.3-pentadecylcatechol
3,3',4,5'-tetrahydroxystilbeneA 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-dihydroxyacetophenoneA dihydroxyacetophenone that is acetophenone carrying hydroxy groups at positions 3' and 4'.3,4-dihydroxyacetophenone; 3',4'-dihydroxyacetophenone
3,4-dihydroxybenzylamine3,4-dihydroxybenzylamine
3,4-dihydroxymandelic acidA catechol that is the 3,4-dihydroxy derivative of mandelic acid; a metabolite of L-dopa.3,4-dihydroxymandelic acid
3,4-dihydroxyphenylacetaldehydeA phenylacetaldehyde in which the 3 and 4 positions of the phenyl group are substituted by hydroxy groups.3,4-dihydroxyphenylacetaldehyde
3,4-dihydroxyphenylacetic acidA 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-dihydroxyphenylethanolA 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-dihydroxyphenylglycolA tetrol composed of ethyleneglycol having a 3,4-dihydroxyphenyl group at the 1-position.3,4-dihydroxyphenylethyleneglycol
3,4-dihydroxyphenylglycolaldehydeA 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 acid3-(3,4-dihydroxyphenyl)lactic acid
3',4'-dihydroxyauroneA 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-diol4-[(1S)-1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol
4-bromocatechol4-Bromocatechol
4-ethylcatechol4-Ethyl-1,2-benzenediol
4-fluorocatechol4-Fluorocatechol
4-hydroxyestroneA 4-hydroxy steroid that is estrone substituted by a hydroxy group at position 4.4-hydroxyestrone
4-nitrocatecholA 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 acidA 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-fluoronorepinephrine4-(2-amino-1-hydroxyethyl)-5-fluorobenzene-1,2-diol
a 32534-Aminocatechol
a 77636An 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
acteosideA 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-490A 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
altenusinA 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 dopamineArachidonoyl dopamine
aspalathinA 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
benserazideA 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
brazilinA organic heterotetracyclic compound that is a red pigment obtained from the wood of Caesalpinia echinata (Brazil-wood) or Caesalpinia sappan (sappan-wood).brazilin
caffeic acidA 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
capsazepineA 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
carbidopa3-(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)
carbidopaThe 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
catecholA benzenediol comprising of a benzene core carrying two hydroxy substituents ortho to each other.catechol
chrysobactinA 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
colterolA 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-caffeoyltyramine3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]propanimidic acid
droxidopaA 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 hypotensiondroxidopa
ellagic acidAn 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
entacaponeA 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
enterobactinA macrotriolide produced by certain members of Enterobacteriaceae, e.g. Escherichia coli and Salmonella.enterobactin
ethyl protocatechuateAn 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
ethylnorepinephrineethylnorepinephrine
hispidinFungal metabolite first found in basidiomycete Inonotus hispidus (formerly Polyporus hispidus).hispidin
isoproterenolA 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 hydrochlorideDL-Isoprenaline hydrochloride
lanosolLanosol
masoprocolA 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-dihydroxybenzoateA methyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with methanol.methyl 3,4-dihydroxybenzoate
myxochelin bA 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-acetyldopamineA 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-caffeoyltyramineN-cis-Caffeoyltyramine
n-oleoyldopamineA 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-naphthahydrazideA 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)-alanyldopamine3-amino-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide
norbelladineA phenethylamine alkaloid that is tyramine in which one of the amino hydrogens has been replaced by a 3,4-dihydroxybenzyl group.norbelladine
oleuropeinA 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 aglyconeA 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 acidA dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.3,4-dihydroxybenzoic acid
protosappanin aprotosappanin A
rimiterolrimiterol
salvianolic acid BA member of the class of 1-benzofurans that is an antioxidant and free radical scavenging compound extracted from S. miltiorrhizasalvianolic acid B
salvinAn 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
sappanchalconeA 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 77434A 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 83959A 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-38393A 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
tetrahydroxycurcuminA 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 fAn 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
tolcaponeBenzophenone 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 a232-[(3,4-dihydroxyphenyl)methylidene]propanedinitrile
vanchrobactinA 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 IIAn 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)

TimeframeStudies, Drugs in This Class (%)All Drugs %
pre-199020,889 (41.46)18.7374
1990's10,440 (20.72)18.2507
2000's8,109 (16.10)29.6817
2010's8,406 (16.68)24.3611
2020's2,538 (5.04)2.80

Study Types

Publication TypeStudies, Drugs in This Class (%)All Drugs (%)
Trials1,483 (2.74%)5.53%
Reviews1,314 (2.43%)6.00%
Case Studies608 (1.12%)4.05%
Observational19 (0.04%)0.25%
Other50,725 (93.68%)84.16%