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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:06:04 UTC
HMDB IDHMDB0001229
Secondary Accession Numbers
  • HMDB01229
Metabolite Identification
Common NameDopaquinone
DescriptionDopaquinone is a substrate of enzyme monophenol monooxygenase [EC 1.14.18.1] in tyrosine metabolism pathway (KEGG).
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-benzoquinoneMeSH
Dopaquinone, (S)-isomerMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP-1.9ALOGPS
logP-2.1ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.48 m³·mol⁻¹ChemAxon
Polarizability18.06 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fml-5900000000-3f77b48d5f42d8951324View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9570000000-5d835cfbd2b202044cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufs-0900000000-093c511b443d87916930View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-1900000000-fc3bdef4314080b351c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9200000000-07d0c6318c984ef80e41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-7481c7c6fe6294da272cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0900000000-04347396e1171463fb62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-7900000000-13ce3640966908fffe55View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Feces
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
AlkaptonuriaPw000180Pw000180 greyscalePw000180 simpleNot Available
Disulfiram PathwayPw000431Pw000431 greyscalePw000431 simpleNot Available
Dopamine beta-hydroxylase deficiencyPw000474Pw000474 greyscalePw000474 simpleNot Available
HawkinsinuriaPw000181Pw000181 greyscalePw000181 simpleNot Available
Monoamine oxidase-a deficiency (MAO-A)Pw000509Pw000509 greyscalePw000509 simpleNot Available
Displaying entries 1 - 5 of 8 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothICD details
FecesDetected but not Quantified Adult (>18 years old)BothCCD details
FecesDetected but not Quantified Adult (>18 years old)BothCCD details
FecesDetected but not Quantified Adult (>18 years old)BothICD details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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 ]

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
L-Dopa + Oxygen → Dopaquinone + Waterdetails
L-Tyrosine + Oxygen → Dopaquinone + Waterdetails
L-Dopa + L-Tyrosine + Oxygen → Dopaquinone + L-Dopa + Waterdetails