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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
Structure of 3,4-DIHYDROXYPHENYLACETIC ACID

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)

HIDE SMILES / InChI

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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patterns of cerebrospinal fluid catechols support increased central noradrenergic responsiveness in aging and Alzheimer's disease.
1999 Sep 15
Dopaminergic activity in transgenic mice underexpressing glucocorticoid receptors: effect of antidepressants.
2001
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
Deprenyl stimulates the efflux of monoamines from the rat hypothalamus in vitro.
2001 Apr
Periodic maternal separation of neonatal rats produces region- and gender-specific effects on biogenic amine content in postmortem adult brain.
2001 Apr
Generation and pharmacological analysis of M2 and M4 muscarinic receptor knockout mice.
2001 Apr 27
Oxalic acid stabilizes dopamine, serotonin, and their metabolites in automated liquid chromatography with electrochemical detection.
2001 Apr 5
Degradation of natural polyphenols by methanogenic consortia enriched from digested municipal sludge.
2001 Aug
Continuous phencyclidine treatment induces schizophrenia-like hyperreactivity of striatal dopamine release.
2001 Aug
Dopaminergic input to the ventromedial hypothalamus facilitates the oestrogen-induced luteinizing hormone surge in ewes.
2001 Feb
Differentiation of disulfiram effects on central catecholamines and hepatic ethanol metabolism.
2001 Feb
Changes in striatal electroencephalography and neurochemistry induced by kainic acid seizures are modified by dopamine receptor antagonists.
2001 Feb 16
Central monoamine activity in genetically distinct strains of mice following a psychogenic stressor: effects of predator exposure.
2001 Feb 23
pH-independent large-volume sample stacking of positive or negative analytes in capillary electrophoresis.
2001 Jan
Mice with a partial deficiency of manganese superoxide dismutase show increased vulnerability to the mitochondrial toxins malonate, 3-nitropropionic acid, and MPTP.
2001 Jan
Monoamine compounds in cerebrospinal fluid of healthy subjects punctured without preceding strict bed rest: a pilot study.
2001 Jan
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
Protective effect of quinacrine on striatal dopamine levels in 6-OHDA and MPTP models of Parkinsonism in rodents.
2001 Jan 1
Significance of glutamate and dopamine neurons in the ventral pallidum in the expression of behavioral sensitization to amphetamine.
2001 Jan 19
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
Biochemical and pathological study of endogenous 1-benzyl-1,2,3,4-tetrahydroisoquinoline-induced parkinsonism in the mouse.
2001 Jul 13
Dissociation of prolactin secretion from tuberoinfundibular dopamine activity in late pregnant rats.
2001 Jun
Inhibition of cytochrome P450 2E1 induces an increase in extracellular dopamine in rat substantia nigra: a new metabolic pathway?
2001 Jun 15
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
Adrenergic hyperactivity and metanephrine excess in the nucleus accumbens after prefrontocortical dopamine depletion.
2001 Mar
p-Hydroxyphenylacetate decarboxylase from Clostridium difficile. A novel glycyl radical enzyme catalysing the formation of p-cresol.
2001 Mar
Effects of orphanin FQ on central dopaminergic neuronal activities and prolactin secretion.
2001 Mar
Evidence for a dissociation between MPTP toxicity and tyrosinase activity based on congenic mouse strain susceptibility.
2001 Mar
Expression of sensitization to amphetamine and dynamics of dopamine neurotransmission in different laminae of the rat medial prefrontal cortex.
2001 Mar
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
Differential effects of endomorphin-1 and -2 on amphetamine sensitization: neurochemical and behavioral aspects.
2001 Mar 1
Day/night variations of dopamine ocular content during Xenopus laevis ontogeny.
2001 Mar 16
Increased extracellular DA and normal evoked DA release in the rat striatum after a partial lesion of the substantia nigra.
2001 Mar 2
Inhibition of MAO-A fails to alter cocaine-induced increases in extracellular dopamine and norepinephrine in rat nucleus accumbens.
2001 Mar 5
Prostaglandins play an important role in diurnal changes of tuberoinfundibular dopaminergic neuronal activity and prolactin secretion in ovariectomized, estrogen-treated rats.
2001 May 1
The role of dopamine in the nucleus accumbens and striatum during sexual behavior in the female rat.
2001 May 1
Chronic estrogen treatment replaces striatal dopaminergic function in ovariectomized rats.
2001 May 11
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
Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine.
2001 May 25

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
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 Fri Dec 15 15:22:20 GMT 2023
Edited
by admin
on Fri Dec 15 15:22:20 GMT 2023
Record UNII
KEX5N0R4N5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3,4-DIHYDROXYPHENYLACETIC ACID
Systematic Name English
2-(3,4-DIHYDROXYPHENYL)ACETIC ACID
Systematic Name English
BENZENEACETIC ACID, 3,4-DIHYDROXY-
Systematic Name English
3,4-DIHYDROXYBENZENEACETIC ACID
Systematic Name English
(3,4-DIHYDROXYPHENYL)ACETIC ACID
Systematic Name English
HOMOPROTOCATECHUIC ACID
Common Name English
HMDB01336
Code English
DOPACETIC ACID
Common Name English
NSC-73191
Code English
DIHYDROXYPHENYLACETIC ACID
Systematic Name English
DOPAC
Common Name English
ACETIC ACID, (3,4-DIHYDROXYPHENYL)-
Systematic Name English
Code System Code Type Description
CAS
102-32-9
Created by admin on Fri Dec 15 15:22:20 GMT 2023 , Edited by admin on Fri Dec 15 15:22:20 GMT 2023
PRIMARY
ECHA (EC/EINECS)
203-024-1
Created by admin on Fri Dec 15 15:22:20 GMT 2023 , Edited by admin on Fri Dec 15 15:22:20 GMT 2023
PRIMARY
NSC
73191
Created by admin on Fri Dec 15 15:22:20 GMT 2023 , Edited by admin on Fri Dec 15 15:22:20 GMT 2023
PRIMARY
WIKIPEDIA
3,4-Dihydroxyphenylacetic acid
Created by admin on Fri Dec 15 15:22:20 GMT 2023 , Edited by admin on Fri Dec 15 15:22:20 GMT 2023
PRIMARY
CHEBI
41941
Created by admin on Fri Dec 15 15:22:20 GMT 2023 , Edited by admin on Fri Dec 15 15:22:20 GMT 2023
PRIMARY
DRUG BANK
DB01702
Created by admin on Fri Dec 15 15:22:20 GMT 2023 , Edited by admin on Fri Dec 15 15:22:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID9074430
Created by admin on Fri Dec 15 15:22:20 GMT 2023 , Edited by admin on Fri Dec 15 15:22:20 GMT 2023
PRIMARY
FDA UNII
KEX5N0R4N5
Created by admin on Fri Dec 15 15:22:20 GMT 2023 , Edited by admin on Fri Dec 15 15:22:20 GMT 2023
PRIMARY
PUBCHEM
547
Created by admin on Fri Dec 15 15:22:20 GMT 2023 , Edited by admin on Fri Dec 15 15:22:20 GMT 2023
PRIMARY
Related Record Type Details
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
PARENT -> METABOLITE
PLASMA; URINE