Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H8O4 |
Molecular Weight | 168.1467 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC1=CC(O)=C(O)C=C1
InChI
InChIKey=CFFZDZCDUFSOFZ-UHFFFAOYSA-N
InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
Molecular Formula | C8H8O4 |
Molecular Weight | 168.1467 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
3, 4-dihydroxyphenylacetic acid (DOPAC) is a neuronal metabolite of dopamine (DA). DA undergoes monoamine oxidase-catalyzed oxidative deamination to 3,4-dihydroxyphenylacetaldehyde (DOPAL), which is metabolized primarily to 3,4-dihydroxyphenylacetic acid (DOPAC) via aldehyde dehydrogenase, ALDH2. DOPAC exhibits the antiproliferative effect in colon cancer cells. In addition, DOPAC enhances not only the total ALDH activity but also the gene expression of ALDH1A1, ALDH2, and ALDH3A1 in a concentration-dependent manner. The pretreatment of DOPAC completely protects the cells from the acetaldehyde-induced cytotoxicity, thus DOPAC acts as a potential ALDH inducer to prevent the alcohol-induced abnormal reaction.
Approval Year
PubMed
Title | Date | PubMed |
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Patterns of cerebrospinal fluid catechols support increased central noradrenergic responsiveness in aging and Alzheimer's disease. | 1999 Sep 15 |
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Dopaminergic activity in transgenic mice underexpressing glucocorticoid receptors: effect of antidepressants. | 2001 |
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Effect of GBR 12909 and fluoxetine on the acute and long term changes induced by MDMA ('ecstasy') on the 5-HT and dopamine concentrations in mouse brain. | 2001 |
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Deprenyl stimulates the efflux of monoamines from the rat hypothalamus in vitro. | 2001 Apr |
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Periodic maternal separation of neonatal rats produces region- and gender-specific effects on biogenic amine content in postmortem adult brain. | 2001 Apr |
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Generation and pharmacological analysis of M2 and M4 muscarinic receptor knockout mice. | 2001 Apr 27 |
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Oxalic acid stabilizes dopamine, serotonin, and their metabolites in automated liquid chromatography with electrochemical detection. | 2001 Apr 5 |
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Degradation of natural polyphenols by methanogenic consortia enriched from digested municipal sludge. | 2001 Aug |
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Continuous phencyclidine treatment induces schizophrenia-like hyperreactivity of striatal dopamine release. | 2001 Aug |
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Dopaminergic input to the ventromedial hypothalamus facilitates the oestrogen-induced luteinizing hormone surge in ewes. | 2001 Feb |
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Differentiation of disulfiram effects on central catecholamines and hepatic ethanol metabolism. | 2001 Feb |
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Changes in striatal electroencephalography and neurochemistry induced by kainic acid seizures are modified by dopamine receptor antagonists. | 2001 Feb 16 |
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Central monoamine activity in genetically distinct strains of mice following a psychogenic stressor: effects of predator exposure. | 2001 Feb 23 |
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pH-independent large-volume sample stacking of positive or negative analytes in capillary electrophoresis. | 2001 Jan |
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Mice with a partial deficiency of manganese superoxide dismutase show increased vulnerability to the mitochondrial toxins malonate, 3-nitropropionic acid, and MPTP. | 2001 Jan |
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Monoamine compounds in cerebrospinal fluid of healthy subjects punctured without preceding strict bed rest: a pilot study. | 2001 Jan |
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The central aromatic amino acid DOPA decarboxylase inhibitor, NSD-1015, does not inhibit L-DOPA-induced circling in unilateral 6-OHDA-lesioned-rats. | 2001 Jan |
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Protective effect of quinacrine on striatal dopamine levels in 6-OHDA and MPTP models of Parkinsonism in rodents. | 2001 Jan 1 |
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Significance of glutamate and dopamine neurons in the ventral pallidum in the expression of behavioral sensitization to amphetamine. | 2001 Jan 19 |
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Cloning of the genes for a 4-sulphocatechol-oxidizing protocatechuate 3,4-dioxygenase from Hydrogenophaga intermedia S1 and identification of the amino acid residues responsible for the ability to convert 4-sulphocatechol. | 2001 Jul |
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Biochemical and pathological study of endogenous 1-benzyl-1,2,3,4-tetrahydroisoquinoline-induced parkinsonism in the mouse. | 2001 Jul 13 |
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Dissociation of prolactin secretion from tuberoinfundibular dopamine activity in late pregnant rats. | 2001 Jun |
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Inhibition of cytochrome P450 2E1 induces an increase in extracellular dopamine in rat substantia nigra: a new metabolic pathway? | 2001 Jun 15 |
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Food restriction-like effects of dietary dehydroepiandrosterone. Hypothalamic neurotransmitters and metabolites in male C57BL/6 and (C57BL/6 x DBA/2)F1 mice. | 2001 Mar |
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Adrenergic hyperactivity and metanephrine excess in the nucleus accumbens after prefrontocortical dopamine depletion. | 2001 Mar |
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p-Hydroxyphenylacetate decarboxylase from Clostridium difficile. A novel glycyl radical enzyme catalysing the formation of p-cresol. | 2001 Mar |
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Effects of orphanin FQ on central dopaminergic neuronal activities and prolactin secretion. | 2001 Mar |
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Evidence for a dissociation between MPTP toxicity and tyrosinase activity based on congenic mouse strain susceptibility. | 2001 Mar |
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Expression of sensitization to amphetamine and dynamics of dopamine neurotransmission in different laminae of the rat medial prefrontal cortex. | 2001 Mar |
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Ovulation delay induced by blockade of the cholinergic system on dioestrus-1, is related to changes in dopaminergic activity of the preoptic anterior-hypothalamic area of the rat. | 2001 Mar 1 |
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Differential effects of endomorphin-1 and -2 on amphetamine sensitization: neurochemical and behavioral aspects. | 2001 Mar 1 |
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Day/night variations of dopamine ocular content during Xenopus laevis ontogeny. | 2001 Mar 16 |
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Increased extracellular DA and normal evoked DA release in the rat striatum after a partial lesion of the substantia nigra. | 2001 Mar 2 |
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Inhibition of MAO-A fails to alter cocaine-induced increases in extracellular dopamine and norepinephrine in rat nucleus accumbens. | 2001 Mar 5 |
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Prostaglandins play an important role in diurnal changes of tuberoinfundibular dopaminergic neuronal activity and prolactin secretion in ovariectomized, estrogen-treated rats. | 2001 May 1 |
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The role of dopamine in the nucleus accumbens and striatum during sexual behavior in the female rat. | 2001 May 1 |
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Chronic estrogen treatment replaces striatal dopaminergic function in ovariectomized rats. | 2001 May 11 |
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BIA 3-202, a novel catechol-O-methyltransferase inhibitor, enhances the availability of L-DOPA to the brain and reduces its O-methylation. | 2001 May 18 |
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Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine. | 2001 May 25 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28828965
Curator's Comment: 3,4-Dihydroxyphenylacetic acid (DOPAC) was shown to enhance not only the total ALDH activity, but also the gene expression of ALDH1A1, ALDH2 and ALDH3A1 in a concentration-dependent manner. DOPAC simultaneously stimulated the nuclear translocation of NFE2-related factor 2 and aryl hydrocarbon receptor. The pretreatment of DOPAC completely protected the cells from the acetaldehyde-induced cytotoxicity. The present study suggested that DOPAC acts as a potential ALDH inducer to prevent the alcohol-induced abnormal reaction.
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:22:20 GMT 2023
by
admin
on
Fri Dec 15 15:22:20 GMT 2023
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Record UNII |
KEX5N0R4N5
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Record Status |
Validated (UNII)
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203-024-1
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73191
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3,4-Dihydroxyphenylacetic acid
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41941
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DB01702
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KEX5N0R4N5
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547
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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
Excretion of 3,4-Dihydroxyphenylacetic acid in the urine of human subjects (n=6, 0-24hr total) after rutin (176 micromoles) supplemented tomato juice; Unit: micromoles
IN-VIVO
URINE
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PARENT -> METABOLITE |
PLASMA; URINE
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