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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-09-22 21:06:35 UTC
HMDB IDHMDB01336
Secondary Accession NumbersNone
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 to 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 striata. 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 ).
Structure
Thumb
Synonyms
ValueSource
3,4-Dihydroxyphenylacetic acidKegg
HomoprotocatechuateKegg
3,4-DihydroxyphenylacetateGenerator
3,4-DihydroxybenzeneacetateGenerator
Homoprotocatechuic acidGenerator
(3,4-Dihydroxyphenyl)-acetic acidHMDB
(3,4-Dihydroxyphenyl)acetateHMDB
(3,4-Dihydroxyphenyl)acetic acidHMDB
2-(3,4-Dihydroxyphenyl)acetic acidHMDB
3,4-DHPOPHMDB
3,4-Dihydroxy-benzeneacetic acidHMDB
3,4-Dihydroxy-phenylacetic acidHMDB
3,4-Dihydroxyphenyl acetateHMDB
3,4-Dihydroxyphenyl acetic acidHMDB
DHYHMDB
DihydroxyphenylacetateHMDB
Dihydroxyphenylacetic acidHMDB
DOPACHMDB
DopacetateHMDB
Dopacetic 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=C(O)C(O)=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 KeyInChIKey=CFFZDZCDUFSOFZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • 1,2-diphenol
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.33 m3·mol-1ChemAxon
Polarizability15.71 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-004i-0942000000-54f714e694a7c3daeaf4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-004i-0931000000-c4bb79d921fb42cf1b40View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9310000000-9490bd0ec921894341f4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-0952000000-d45a1420d6ae61cb9169View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-3e7377f36ca2547f4885View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-60e1fc55d54131c2923eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fi0-9400000000-c63542b296bac95866e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-579796710abc38249c3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-22f8a4f4efd0f10804b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9700000000-42b3de6bccbc10ad7b48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-579796710abc38249c3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-22f8a4f4efd0f10804b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9700000000-42b3de6bccbc10ad7b48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-a59d2cab0d3d859760a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1900000000-6f630370c11294562cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-a45be46f3b52664dd4d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-a59d2cab0d3d859760a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1900000000-6f630370c11294562cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-a45be46f3b52664dd4d1View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Location
  • Brain
  • Hypothalamus
  • Neuron
  • Striatum
Pathways
NameSMPDB LinkKEGG Link
AlkaptonuriaSMP00169Not Available
Disulfiram PathwaySMP00429Not Available
Dopamine beta-hydroxylase deficiencySMP00498Not Available
HawkinsinuriaSMP00190Not Available
Monoamine oxidase-a deficiency (MAO-A)SMP00533Not Available
Tyrosine MetabolismSMP00006map00350
Tyrosinemia Type ISMP00218Not Available
Tyrosinemia, transient, of the newbornSMP00494Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572
  • Not Applicable
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 and Quantified13.56 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified28.368 +/- 21.113 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified39.549 +/- 48.529 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified40.857 +/- 59.710 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedBoth
Normal
details
FecesDetected and Quantified22.124 +/- 5.174 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 572
  • Not Applicable
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 QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.34 +/- 1.49 umol/mmol creatinineAdult (>18 years old)BothNormal 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
BiofluidStatusValueAgeSexConditionReferenceDetails
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
Associated Disorders and Diseases
Disease References
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. [10494443 ]
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. [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. [9849813 ]
Associated OMIM IDs
DrugBank IDDB01702
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID572
Phenol Explorer Metabolite ID572
FoodDB IDFDB000316
KNApSAcK IDC00040996
Chemspider ID532
KEGG Compound IDC01161
BioCyc IDCPD-782
BiGG ID36946
Wikipedia LinkDOPAC
NuGOwiki LinkHMDB01336
Metagene LinkHMDB01336
METLIN ID6170
PubChem Compound547
PDB IDDHY
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. 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. [12649306 ]
  2. 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. [9931050 ]
  3. 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. [10494443 ]
  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. [9849813 ]
  5. 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. [8884658 ]
  6. 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. [3572399 ]
  7. 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. [743624 ]
  8. Braestrup C: Biochemical differentiation of amphetamine vs methylphenidate and nomifensine in rats. J Pharm Pharmacol. 1977 Aug;29(8):463-70. [19594 ]
  9. 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. [15191803 ]
  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. [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. [6891440 ]
  12. 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. [560969 ]
  13. 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. [2597314 ]
  14. 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. [1309230 ]
  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. [41042 ]
  16. 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. [3152003 ]
  17. 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. [9323127 ]
  18. 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. [2415677 ]
  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. [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 Nevropatol Psikhiatr Im S S Korsakova. 1995;95(6):52-6. [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. [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. [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. [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. [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. [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. [16365058 ]

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 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