Showing metabocard for Topaquinone (BMDB0011639)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:22:08 UTC
Update Date2020-04-22 15:45:43 UTC
BMDB IDBMDB0011639
Secondary Accession Numbers
  • BMDB11639
Metabolite Identification
Common NameTopaquinone
DescriptionTopaquinone 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. Topaquinone is possibly soluble (in water) and a very strong basic compound (based on its pKa). Topaquinone exists in all living organisms, ranging from bacteria to humans. In cattle, topaquinone is involved in a few metabolic pathways, which include the tyrosine metabolism pathway, the beta-alanine metabolism pathway, and the histidine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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)-tautomerHMDB
6-Hydroxyphenylalanine-3,4-dioneHMDB
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
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
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-2.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)8.78ChemAxon
Physiological Charge-1ChemAxon
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
BioavailabilityYesChemAxon
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, Positivesplash10-00kf-4900000000-8000fefca905c692c6bbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9155000000-9f62f7d6a569a845f191View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0790000000-264298b854c17cbd06c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-fa2a9a83c16bdc9743e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4900000000-edaf20a2d8ee4a49ed50View 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, Positivesplash10-03dr-0950000000-5c274a2daa8ac5fdb60fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-1900000000-75224325d6d90326a3ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-fb2113307dcb393ca87bView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011639
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028336
KNApSAcK IDNot Available
Chemspider ID110408
KEGG Compound IDNot Available
BioCyc IDNot Available
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Primary amine oxidase, liver isozyme
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q29437
Molecular weight:
84757.0
Enzyme Details
2. Membrane primary amine oxidase
General function:
Secondary metabolites biosynthesis, transport and catabolism
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 (By similarity).
Gene Name:
AOC3
Uniprot ID:
Q9TTK6
Molecular weight:
84500.0
Enzyme Details
3. Primary amine oxidase, lung isozyme
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
O46406
Molecular weight:
84883.0