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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:32 UTC
HMDB IDHMDB0001229
Secondary Accession Numbers
  • HMDB01229
Metabolite Identification
Common NameDopaquinone
DescriptionDopaquinone, also known as o-dopaquinone or L-dopaquinone, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha-amino acids which have the L-configuration of the alpha-carbon atom. Dopaquinone is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-Dopaquinone is a metabolite of L-DOPA and a precursor of melanin. Melanin is synthesized from tyrosine by hydroxylation to dihydroxyphenylalanine (DOPA) and subsequent oxidation to dopaquinone. Both reactions are catalyzed by the enzyme tyrosinase, which is the rate-limiting step. Dopaquinone has an ortho-quinone ring, which is known to be neurotoxic and highly reactive with many other compounds (PMID: 413870 ). Dopaquinone typically combines with cysteine to form pheomelanin (a pigment-polymer). Alternatively, dopaquinone can be converted to leucodopachrome and eventually to eumelanin (also a pigment-polymer). Dopaquinone can be found in skin and feces. Within the cell, dopaquinone is primarily located in the cytoplasm. Dopaquinone is involved in several metabolic disorders, some of which include transient tyrosinemia, hawkinsinuria, tyrosinemia type I, and alkaptonuria. Chronically high levels of dopaquinone are associated with Parkinson's disease (PD). Many Parkinson's patients are treated with L-DOPA. However, long-term treatment with L-DOPA may actually worsen symptoms or result in neurotic and psychotic symptoms. These may be due to dopachrome and dopaquinone accumulating in the brain of L-DOPA treated patients (PMID: 19131041 , PMID: 12373519 ).
Structure
Thumb
Synonyms
ValueSource
(S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoateChEBI
(S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acidGenerator
O-DopaquinoneHMDB
4-(2-Carboxy-2-aminoethyl)-1,2-benzoquinoneHMDB
Dopaquinone, (S)-isomerHMDB
L-DopaquinoneHMDB
Chemical FormulaC9H9NO4
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
IUPAC Name(2S)-2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
Traditional Namedopaquinone
CAS Registry Number4430-97-1
SMILES
N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)/t6-/m0/s1
InChI KeyAHMIDUVKSGCHAU-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • O-benzoquinone
  • Quinone
  • Ketone
  • Amino acid
  • Cyclic ketone
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCCD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIleal Crohn's disease details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022501
KNApSAcK IDNot Available
Chemspider ID388447
KEGG Compound IDC00822
BioCyc IDDOPAQUINONE
BiGG ID36114
Wikipedia LinkL-Dopaquinone
METLIN ID354
PubChem Compound439316
PDB IDNot Available
ChEBI ID16852
Food Biomarker OntologyNot Available
VMH IDDOPAQN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLand E J; Riley P A Spontaneous redox reactions of dopaquinone and the balance between the eumelanic and phaeomelanic pathways. Pigment cell research / sponsored by the European Society for Pigment Cell Research and the International Pigment Cell Society (2000), 13(4), 273-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rorsman H, Tegner E: Biochemical observations in UV-induced pigmentation. Photodermatol. 1988 Feb;5(1):30-8. [PubMed:3281148 ]
  2. Tsukamoto K, Furue M, Sato Y, Takayama O, Akasu R, Ohtake N, Wakamatsu K, Ito S, Tamaki K, Shimada S: Generalized melanosis in metastatic malignant melanoma: the possible role of DOPAquinone metabolites. Dermatology. 1998;197(4):338-42. [PubMed:9873171 ]
  3. Graham DG, Tiffany SM, Vogel FS: The toxicity of melanin precursors. J Invest Dermatol. 1978 Feb;70(2):113-6. [PubMed:413870 ]
  4. Hattoria N, Wanga M, Taka H, Fujimura T, Yoritaka A, Kubo S, Mochizuki H: Toxic effects of dopamine metabolism in Parkinson's disease. Parkinsonism Relat Disord. 2009 Jan;15 Suppl 1:S35-8. doi: 10.1016/S1353-8020(09)70010-0. [PubMed:19131041 ]
  5. Kostrzewa RM, Kostrzewa JP, Brus R: Neuroprotective and neurotoxic roles of levodopa (L-DOPA) in neurodegenerative disorders relating to Parkinson's disease. Amino Acids. 2002;23(1-3):57-63. doi: 10.1007/s00726-001-0110-x. [PubMed:12373519 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
Reactions
DOPA + Oxygen → Dopaquinone + Waterdetails
L-Tyrosine + Oxygen → Dopaquinone + Waterdetails
DOPA + L-Tyrosine + Oxygen → Dopaquinone + DOPA + Waterdetails