ContaminantDB: Topaquinone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 20:35:16 UTC

Update Date

2016-11-09 01:22:14 UTC

Accession Number

CHEM040379

Identification

Common Name

Topaquinone

Class

Small Molecule

Description

Topaquinone 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.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-a-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoate	HMDB
(S)-a-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acid	HMDB
(S)-alpha-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoate	HMDB
(S)-alpha-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acid	HMDB
2,4,5-Trihydroxyphenylalanine quinone	HMDB
6-Hydroxydopa quinone	HMDB
6-Hydroxydopaquinone	HMDB
a-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoate	HMDB
a-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acid	HMDB
alpha-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoate	HMDB
alpha-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acid	HMDB
O-Topaquinone	HMDB
Topa quinone	HMDB
TPQ	HMDB
6-Hydroxydopa quinone, (6-OH-3,4-dioxo)-tautomer	HMDB
6-Hydroxyphenylalanine-3,4-dione	HMDB

Chemical Formula

C₉H₉NO₅

Average Molecular Mass

211.172 g/mol

Monoisotopic Mass

211.048 g/mol

CAS Registry Number

64192-68-3

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

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 Key

YWRFBISQAMHSIX-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.86 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.37 m³·mol⁻¹	ChemAxon
Polarizability	18.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-4900000000-8000fefca905c692c6bb	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-006x-9155000000-9f62f7d6a569a845f191	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0490000000-10cc522af99cf25fa607	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03kl-2930000000-faaea6b1c3327a320404	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9500000000-8e842526e55c7606e107	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0790000000-264298b854c17cbd06c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-fa2a9a83c16bdc9743e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-4900000000-edaf20a2d8ee4a49ed50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02tc-0920000000-d016b4dc13ff26872de2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-1900000000-e9e660167189a0f3df7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-e330ba78cb2c450f79af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dr-0950000000-5c274a2daa8ac5fdb60f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-1900000000-75224325d6d90326a3ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-5900000000-fb2113307dcb393ca87b	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0011639

FooDB ID

FDB028336

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

ECMDB21455

References

Synthesis Reference

Not Available

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.

Topaquinone (CHEM040379)

Structure for CHEM040379: Topaquinone