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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:54 UTC
HMDB IDHMDB0001336
Secondary Accession Numbers
  • HMDB01336
Metabolite 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 ).
Structure
Data?1563860694
Synonyms
ValueSource
2-(3,4-DIHYDROXYPHENYL)acetIC ACIDChEBI
3,4-Dihydroxyphenyl acetic acidChEBI
3,4-Dihydroxyphenylacetic acidChEBI
Dopacetic acidChEBI
Homoprotocatechuic acidChEBI
HomoprotocatechuateKegg
2-(3,4-DIHYDROXYPHENYL)acetateGenerator
3,4-Dihydroxyphenyl acetateGenerator
3,4-DihydroxyphenylacetateGenerator
DopacetateGenerator
3,4-DihydroxybenzeneacetateGenerator
DOPACHMDB
3,4 Dihydroxyphenylacetic acidHMDB
3,4-Dihydroxyphenylacetic acid, monosodium saltHMDB
(3,4-Dihydroxyphenyl)-acetic acidHMDB
(3,4-Dihydroxyphenyl)acetateHMDB
(3,4-Dihydroxyphenyl)acetic acidHMDB
3,4-DHPOPHMDB
3,4-Dihydroxy-benzeneacetic acidHMDB
3,4-Dihydroxy-phenylacetic acidHMDB
DHYHMDB
DihydroxyphenylacetateHMDB
Dihydroxyphenylacetic acidHMDB
HAAHMDB
Homogentisic acidHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-(3,4-dihydroxyphenyl)acetic acid
Traditional Name3,4 dihydroxyphenylacetic acid
CAS Registry Number102-32-9
SMILES
OC(=O)CC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
InChI KeyCFFZDZCDUFSOFZ-UHFFFAOYSA-N
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
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point168 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4 mg/mLNot Available
LogP0.98SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility7.23 g/LALOGPS
logP0.93ALOGPS
logP1ChemAxon
logS-1.4ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-004i-0942000000-54f714e694a7c3daeaf4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0931000000-c4bb79d921fb42cf1b40JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9310000000-9490bd0ec921894341f4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-0952000000-d45a1420d6ae61cb9169JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0942000000-54f714e694a7c3daeaf4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0931000000-c4bb79d921fb42cf1b40JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9310000000-9490bd0ec921894341f4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-0952000000-d45a1420d6ae61cb9169JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0931000000-3fab9c521f7f85372b94JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3900000000-9badffe195f5e0ba98e0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-4093000000-178e6eeb94df071e6c15JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-3e7377f36ca2547f4885JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-60e1fc55d54131c2923eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fi0-9400000000-c63542b296bac95866e2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-709dd9faccdbbb3dc088JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-579796710abc38249c3aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-22f8a4f4efd0f10804b5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9700000000-42b3de6bccbc10ad7b48JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-579796710abc38249c3aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-22f8a4f4efd0f10804b5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9700000000-42b3de6bccbc10ad7b48JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-a59d2cab0d3d859760a7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1900000000-6f630370c11294562cb7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-a45be46f3b52664dd4d1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-a59d2cab0d3d859760a7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1900000000-6f630370c11294562cb7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-a45be46f3b52664dd4d1JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Brain
  • Hypothalamus
  • Neuron
  • Striatum
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
BloodDetected and Quantified0.019 +/- 0.009 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.01 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.008 +/- 0.004 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.016 +/- 0.006 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.015 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.003 +/- 0.001 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.003 +/- 0.001 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.003 +/- 0.001 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.014 +/- 0.012 uMAdult (>18 years old)Male
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0001 +/- 0.00002 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.003 +/- 0.0015 (0.0013 - 0.0045) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.002 +/- 0.001 (0.001 - 0.003) uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified13.56 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected and Quantified28.368 +/- 21.113 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected and Quantified39.549 +/- 48.529 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified40.857 +/- 59.710 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Not SpecifiedBoth
Normal
details
FecesDetected and Quantified22.124 +/- 5.174 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572 details
UrineDetected and Quantified1.16 +/- 0.50 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.05 (0.02-0.11) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.34 +/- 1.49 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.337 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0340-3.310 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.48 +/- 0.4 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.9(0.6-1.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.044 +/- 0.006 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 +/- 0.003 uMAdult (>18 years old)Not SpecifiedEncephalitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0001 (0.000070-0.00013) uMAdult (>18 years old)BothHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0001 +/- 0.00003 uMAdult (>18 years old)BothHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0023 (0.00051-0.0042) uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Encephalitis
  1. Kalita J, Kumar S, Vijaykumar K, Palit G, Misra UK: A study of CSF catecholamine and its metabolites in acute and convalescent period of encephalitis. J Neurol Sci. 2007 Jan 15;252(1):62-6. Epub 2006 Nov 28. [PubMed:17134724 ]
Hypothyroidism
  1. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
Alzheimer's disease
  1. Raskind MA, Peskind ER, Holmes C, Goldstein DS: Patterns of cerebrospinal fluid catechols support increased central noradrenergic responsiveness in aging and Alzheimer's disease. Biol Psychiatry. 1999 Sep 15;46(6):756-65. [PubMed:10494443 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB01702
Phenol Explorer Compound ID572
FoodDB IDFDB000316
KNApSAcK IDC00040996
Chemspider ID532
KEGG Compound IDC01161
BioCyc IDCPD-782
BiGG ID36946
Wikipedia LinkDOPAC
METLIN ID6170
PubChem Compound547
PDB IDNot Available
ChEBI ID41941
References
Synthesis ReferenceJoray, Marcel; Breuninger, Manfred. Process for the preparation of phenolic compounds. PCT Int. Appl. (2007), 15pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Raskind MA, Peskind ER, Holmes C, Goldstein DS: Patterns of cerebrospinal fluid catechols support increased central noradrenergic responsiveness in aging and Alzheimer's disease. Biol Psychiatry. 1999 Sep 15;46(6):756-65. [PubMed:10494443 ]
  2. Braestrup C: Biochemical differentiation of amphetamine vs methylphenidate and nomifensine in rats. J Pharm Pharmacol. 1977 Aug;29(8):463-70. [PubMed:19594 ]
  3. Nakao N, Shintani-Mizushima A, Kakishita K, Itakura T: The ability of grafted human sympathetic neurons to synthesize and store dopamine: a potential mechanism for the clinical effect of sympathetic neuron autografts in patients with Parkinson's disease. Exp Neurol. 2004 Jul;188(1):65-73. [PubMed:15191803 ]
  4. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
  5. 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 ]
  6. 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 ]
  7. Panholzer TJ, Beyer J, Lichtwald K: Coupled-column liquid chromatographic analysis of catecholamines, serotonin, and metabolites in human urine. Clin Chem. 1999 Feb;45(2):262-8. [PubMed:9931050 ]
  8. Van Loon GR, De Souza EB, Kim C: Alterations in brain dopamine and serotonin metabolism during the development of tolerance to human beta-endorphin in rats. Can J Physiol Pharmacol. 1978 Dec;56(6):1067-71. [PubMed:743624 ]
  9. Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [PubMed:8884658 ]
  10. Gramsch C, Blasig J, Herz A: Changes in striatal dopamine metabolism during precipitated morphine withdrawal. Eur J Pharmacol. 1977 Aug 1;44(3):231-40. [PubMed:560969 ]
  11. Fornstedt B, Brun A, Rosengren E, Carlsson A: The apparent autoxidation rate of catechols in dopamine-rich regions of human brains increases with the degree of depigmentation of substantia nigra. J Neural Transm Park Dis Dement Sect. 1989;1(4):279-95. [PubMed:2597314 ]
  12. Garrett MC, Soares-da-Silva P: Increased cerebrospinal fluid dopamine and 3,4-dihydroxyphenylacetic acid levels in Huntington's disease: evidence for an overactive dopaminergic brain transmission. J Neurochem. 1992 Jan;58(1):101-6. [PubMed:1309230 ]
  13. 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 ]
  14. Tekes K, Tothfalusi L, Gaal J, Magyar K: Effect of MAO inhibitors on the uptake and metabolism of dopamine in rat and human brain. Pol J Pharmacol Pharm. 1988 Nov-Dec;40(6):653-8. [PubMed:3152003 ]
  15. Rubinstein M, Phillips TJ, Bunzow JR, Falzone TL, Dziewczapolski G, Zhang G, Fang Y, Larson JL, McDougall JA, Chester JA, Saez C, Pugsley TA, Gershanik O, Low MJ, Grandy DK: Mice lacking dopamine D4 receptors are supersensitive to ethanol, cocaine, and methamphetamine. Cell. 1997 Sep 19;90(6):991-1001. [PubMed:9323127 ]
  16. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
  17. Hutson PH, Curzon G: Dopamine metabolites in rat cisternal cerebrospinal fluid: major contribution from extrastriatal dopamine neurones. J Neurochem. 1986 Jan;46(1):186-90. [PubMed:2415677 ]
  18. Ebinger G, Michotte Y, Herregodts P: The significance of homovanillic acid and 3,4-dihydroxyphenylacetic acid concentrations in human lumbar cerebrospinal fluid. J Neurochem. 1987 Jun;48(6):1725-9. [PubMed:3572399 ]
  19. Thurmond JB, Brown JW: Effect of brain monoamine precursors on stress-induced behavioral and neurochemical changes in aged mice. Brain Res. 1984 Mar 26;296(1):93-102. [PubMed:6201238 ]
  20. Kogan BM, Tkachenko AA, Drozdov AZ, Andrianova EP, Filatova TS, Man'kovskaia IV, Kovaleva IA: [Monoamine metabolism in different forms of paraphilias]. Zh Nevrol Psikhiatr Im S S Korsakova. 1995;95(6):52-6. [PubMed:8788979 ]
  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 ]
  23. Cadet JL, Ali SF, Rothman RB, Epstein CJ: Neurotoxicity, drugs and abuse, and the CuZn-superoxide dismutase transgenic mice. Mol Neurobiol. 1995 Aug-Dec;11(1-3):155-63. [PubMed:8561959 ]
  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 ]
  28. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
S-Adenosylmethionine + 3,4-Dihydroxybenzeneacetic acid → S-Adenosylhomocysteine + Homovanillic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
3,4-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
3,4-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3,4-Dihydroxybenzeneacetic acid → 6-[4-(carboxymethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,4-Dihydroxybenzeneacetic acid → 6-[5-(carboxymethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,4-Dihydroxybenzeneacetic acid → 6-{[2-(3,4-dihydroxyphenyl)acetyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
3,4-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
3,4-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3,4-Dihydroxybenzeneacetic acid → 2-[4-hydroxy-3-(sulfooxy)phenyl]acetic aciddetails