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Showing Compound Topaquinone (FDB028336)

Record Information
Version1.0
Creation date2011-09-21 01:38:11 UTC
Update date2020-09-17 15:41:36 UTC
Primary IDFDB028336
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTopaquinone
DescriptionTopaquinone, also known as TPQ, 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 a very strong basic compound (based on its pKa). Topaquinone exists in all living organisms, ranging from bacteria to humans. This residue catalyses its own transition, first to dopaquinone and then to topaquinone, in a Cu2+ dependent manner. It is used by copper amine oxidases which contain a tyrosine residue near the active site. In humans, topaquinone is involved in the metabolic disorder called tyrosinemia, transient, of the newborn. Its structure was first identified in 1990. Topaquinone (TPQ) is a redox cofactor derived from the amino acid tyrosine. Its name derives from 2,4,5-trihydroxyphenylalanine-quinone.
CAS Number64192-68-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
(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
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
Topaquinonehmdb
Predicted Properties
PropertyValueSource
Water Solubility1.86 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H9NO5
IUPAC name(2S)-2-amino-3-(6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
InChI IdentifierInChI=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
Isomeric SMILESN[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O
Average Molecular Weight211.1715
Monoisotopic Molecular Weight211.048072403
Classification
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
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTopaquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kf-4900000000-8000fefca905c692c6bbSpectrum
Predicted GC-MSTopaquinone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9155000000-9f62f7d6a569a845f191Spectrum
Predicted GC-MSTopaquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02tc-0920000000-d016b4dc13ff26872de2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-e9e660167189a0f3df7bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-e330ba78cb2c450f79afSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0490000000-10cc522af99cf25fa607Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03kl-2930000000-faaea6b1c3327a320404Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9500000000-8e842526e55c7606e107Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dr-0950000000-5c274a2daa8ac5fdb60fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-1900000000-75224325d6d90326a3ceSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-fb2113307dcb393ca87bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0790000000-264298b854c17cbd06c0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-fa2a9a83c16bdc9743e5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4900000000-edaf20a2d8ee4a49ed50Spectrum
NMRNot Available
ChemSpider ID110408
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID123871
Pubchem Substance IDNot Available
ChEBI ID36076
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11639
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference