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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-01-30 15:46:08 UTC
Update Date2019-01-11 19:29:48 UTC
HMDB IDHMDB0011639
Secondary Accession Numbers
  • HMDB11639
Metabolite Identification
Common NameTopaquinone
DescriptionTopaquinone (TPQ), is the quinone of 2,4,5-trihydroxyphenylalanine. TPQ is the cofactor in most copper-containing amine oxidases. It is produced by post-translational modification of a strictly conserved active-site tyrosine residue with the participation of the copper ion at the active site. Once formed, TPQ acts as a switch between the heterolytic transformation of amine substrates to aldehydes, via a pyridoxal phosphate-like Schiff base complex, and one electron chemistry involving reduction of molecular oxygen (PMID: 12686122 ).
Structure
Data?1547234988
Synonyms
ValueSource
(S)-a-amino-6-Hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoateHMDB
(S)-a-amino-6-Hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acidHMDB
(S)-alpha-amino-6-Hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoateHMDB
(S)-alpha-amino-6-Hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acidHMDB
2,4,5-Trihydroxyphenylalanine quinoneHMDB
6-Hydroxydopa quinoneHMDB
6-HydroxydopaquinoneHMDB
a-amino-6-Hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoateHMDB
a-amino-6-Hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acidHMDB
alpha-amino-6-Hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoateHMDB
alpha-amino-6-Hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acidHMDB
O-TopaquinoneHMDB
Topa quinoneHMDB
TPQHMDB
6-Hydroxydopa quinone, (6-OH-3,4-dioxo)-tautomerMeSH
6-Hydroxyphenylalanine-3,4-dioneMeSH
Chemical FormulaC9H9NO5
Average Molecular Weight211.1715
Monoisotopic Molecular Weight211.048072403
IUPAC Name(2S)-2-amino-3-(6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
Traditional Name(2S)-2-amino-3-(6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
CAS Registry Number64192-68-3
SMILES
N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O
InChI Identifier
InChI=1S/C9H9NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11H,1,10H2,(H,14,15)/t5-/m0/s1
InChI KeyYWRFBISQAMHSIX-YFKPBYRVSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Vinylogous acid
  • Ketone
  • Amino acid
  • Cyclic ketone
  • Carboxylic acid
  • Enol
  • Monocarboxylic acid or derivatives
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Process

Naturally occurring process:

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 Solubility1.86 g/LALOGPS
logP-2ALOGPS
logP-2.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.37 m³·mol⁻¹ChemAxon
Polarizability18.85 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-4900000000-8000fefca905c692c6bbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9155000000-9f62f7d6a569a845f191View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02tc-0920000000-d016b4dc13ff26872de2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-e9e660167189a0f3df7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-e330ba78cb2c450f79afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0490000000-10cc522af99cf25fa607View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03kl-2930000000-faaea6b1c3327a320404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9500000000-8e842526e55c7606e107View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028336
KNApSAcK IDNot Available
Chemspider ID110408
KEGG Compound IDNot Available
BioCyc IDTOPAQUINONE
BiGG IDNot Available
Wikipedia LinkTopaquinone
METLIN IDNot Available
PubChem Compound123871
PDB IDNot Available
ChEBI ID36076
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Klinman JP: The multi-functional topa-quinone copper amine oxidases. Biochim Biophys Acta. 2003 Apr 11;1647(1-2):131-7. [PubMed:12686122 ]

Enzymes

General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11