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Record Information
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:13 UTC
NP-MRD IDNP0000956
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,4-Dihydroxybenzeneacetic acid
Description3,4-Dihydroxyphenylacetic acid (DOPAC) is a phenolic 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 into DOPAC via aldehyde dehydrogenase (ALDH2). The biotransformation of DOPAL is critical as previous studies have demonstrated this DA-derived aldehyde to be a reactive electrophile and toxic to dopaminergic cells. Known inhibitors of mitochondrial ALDH2, such as 4-hydroxy-2-nonenal (4HNE) inhibit ALDH2-mediated oxidation of the endogenous neurotoxin DOPAL. 4HNE is one of the resulting products of oxidative stress, thus linking oxidative stress to the uncontrolled production of an endogenous neurotoxin relevant to Parkinson's disease. In early-onset Parkinson disease, there is markedly reduced activities of both monoamine oxidase (MAO) A and B. The amount of DOPAC, which is produced during dopamine oxidation by MAO, is greatly reduced as a result of increased parkin overexpression. Administration of methamphetamine to animals causes loss of DA terminals in the brain and significant decreases in dopamine and dihydroxyphenylacetic acid (DOPAC) in the striatum. Renal dopamine produced in the residual tubular units may be enhanced during a sodium challenge, thus behaving appropriately as a compensatory natriuretic hormone; however, the renal dopaminergic system in patients afflicted with renal parenchymal disorders should address parameters other than free urinary dopamine, namely the urinary excretion of L-DOPA and metabolites. DOPAC is one of the major phenolic acids formed during human microbial fermentation of tea, citrus, and soy flavonoid supplements. DOPAC exhibits a considerable antiproliferative effect in LNCaP prostate cancer and HCT116 colon cancer cells. The antiproliferative activity of DOPAC may be due to its catechol structure. A similar association of the catechol moiety in the B-ring with antiproliferative activity was demonstrated for flavanones (PMID: 16956664 , 16455660 , 8561959 , 11369822 , 10443478 , 16365058 ). DOPAC can be found in Gram-positive bacteria (PMID: 24752840 ).
3,4-Dihydroxyphenyl acetic acidChEBI
3,4-Dihydroxyphenylacetic acidChEBI
Dopacetic acidChEBI
Homoprotocatechuic acidChEBI
3,4-Dihydroxyphenyl acetateGenerator
3,4 Dihydroxyphenylacetic acidHMDB
3,4-Dihydroxyphenylacetic acid, monosodium saltHMDB
(3,4-Dihydroxyphenyl)-acetic acidHMDB
(3,4-Dihydroxyphenyl)acetic acidHMDB
3,4-Dihydroxy-benzeneacetic acidHMDB
3,4-Dihydroxy-phenylacetic acidHMDB
Dihydroxyphenylacetic acidHMDB
Homogentisic acidHMDB
3',4'-Dihydroxyphenylacetic acidHMDB
3,4-Dihydroxyphenylethanoic acid
Chemical FormulaC8H8O4
Average Mass168.1467 Da
Monoisotopic Mass168.04226 Da
IUPAC Name2-(3,4-dihydroxyphenyl)acetic acid
Traditional Name3,4 dihydroxyphenylacetic acid
CAS Registry Number102-32-9
InChI Identifier
Experimental Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Cervus canadensisFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
Olea europaeaFooDB
Ovis ariesFooDB
Phasianus colchicusFooDB
Rubus idaeusFooDB
Secamone afzeliiLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tamarindus indicaFooDB
Taxus baccataKNApSAcK Database
Tragopogon pratensisLOTUS Database
Vaccinium myrtillusFooDB
Vanilla planifolia Jacks.LOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
Experimental Properties
Melting Point168 °CNot Available
Boiling Point418.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility4 mg/mLNot Available
LogP0.98Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
Water Solubility7.23 g/LALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability15.71 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
DrugBank IDDB01702
Phenol Explorer Compound ID572
FoodDB IDFDB030384
KNApSAcK IDC00040996
Chemspider ID532
KEGG Compound IDC01161
BioCyc IDCPD-782
BiGG ID36946
Wikipedia LinkDOPAC
PubChem Compound547
PDB IDNot Available
ChEBI ID41941
Good Scents IDrw1183451
General References
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  10. Annunziato LA, Wuerthele SM, Moore KE: Comparative effects of penfluridol on circling behavior and striatal DOPAC and serum prolactin concentrations in the rat. Eur J Pharmacol. 1978 Aug 1;50(3):187-92. [PubMed:567584 ]
  11. De Simoni MG, Guardabasso V, Misterek K, Algeri S: Similarities and differences between D-ALA2 MET5 enkephalin amide and morphine in the induction of tolerance to their effects on catalepsy and on dopamine metabolism in the rat brain. Naunyn Schmiedebergs Arch Pharmacol. 1982 Nov;321(2):105-11. [PubMed:6891440 ]
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  15. Massotti M, Longo VG: Role of the dopaminergic system in the cataleptogenic action of bulbocapnine. J Pharm Pharmacol. 1979 Oct;31(10):691-5. [PubMed:41042 ]
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  21. Florang VR, Rees JN, Brogden NK, Anderson DG, Hurley TD, Doorn JA: Inhibition of the oxidative metabolism of 3,4-dihydroxyphenylacetaldehyde, a reactive intermediate of dopamine metabolism, by 4-hydroxy-2-nonenal. Neurotoxicology. 2007 Jan;28(1):76-82. Epub 2006 Aug 1. [PubMed:16956664 ]
  22. Jiang H, Jiang Q, Liu W, Feng J: Parkin suppresses the expression of monoamine oxidases. J Biol Chem. 2006 Mar 31;281(13):8591-9. Epub 2006 Feb 2. [PubMed:16455660 ]
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  24. Pestana M, Jardim H, Correia F, Vieira-Coelho MA, Soares-da-Silva P: Renal dopaminergic mechanisms in renal parenchymal diseases and hypertension. Nephrol Dial Transplant. 2001;16 Suppl 1:53-9. [PubMed:11369822 ]
  25. Kim DH, Kim SY, Park SY, Han MJ: Metabolism of quercitrin by human intestinal bacteria and its relation to some biological activities. Biol Pharm Bull. 1999 Jul;22(7):749-51. [PubMed:10443478 ]
  26. Gao K, Xu A, Krul C, Venema K, Liu Y, Niu Y, Lu J, Bensoussan L, Seeram NP, Heber D, Henning SM: Of the major phenolic acids formed during human microbial fermentation of tea, citrus, and soy flavonoid supplements, only 3,4-dihydroxyphenylacetic acid has antiproliferative activity. J Nutr. 2006 Jan;136(1):52-7. [PubMed:16365058 ]
  27. Radkov AD, Moe LA: Bacterial synthesis of D-amino acids. Appl Microbiol Biotechnol. 2014 Jun;98(12):5363-74. doi: 10.1007/s00253-014-5726-3. Epub 2014 Apr 22. [PubMed:24752840 ]