T3DB: L-Dopaquinone

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

Record Information

Version

2.0

Creation Date

2014-10-02 19:01:44 UTC

Update Date

2018-03-21 17:46:23 UTC

Accession Number

T3D4967

Identification

Common Name

L-Dopaquinone

Class

Small Molecule

Description

Dopaquinone, also known as o-dopaquinone or L-dopaquinone, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha-amino acids which have the L-configuration of the alpha-carbon atom. Dopaquinone is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-Dopaquinone is a metabolite of L-DOPA and a precursor of melanin. Melanin is synthesized from tyrosine by hydroxylation to dihydroxyphenylalanine (DOPA) and subsequent oxidation to dopaquinone. Both reactions are catalyzed by the enzyme tyrosinase, which is the rate-limiting step. Dopaquinone has an ortho-quinone ring, which is known to be neurotoxic and highly reactive with many other compounds (PMID: 413870). Dopaquinone typically combines with cysteine to form pheomelanin (a pigment-polymer). Alternatively, dopaquinone can be converted to leucodopachrome and eventually to eumelanin (also a pigment-polymer). Dopaquinone can be found in skin and feces. Within the cell, dopaquinone is primarily located in the cytoplasm. Dopaquinone is involved in several metabolic disorders, some of which include transient tyrosinemia, hawkinsinuria, tyrosinemia type I, and alkaptonuria. Chronically high levels of dopaquinone are associated with Parkinson's disease (PD). Many Parkinson's patients are treated with L-DOPA. However, long-term treatment with L-DOPA may actually worsen symptoms or result in neurotic and psychotic symptoms. These may be due to dopachrome and dopaquinone accumulating in the brain of L-DOPA treated patients (PMID: 19131041, PMID: 12373519).

Compound Type

Animal Toxin
Metabolite
Natural Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
(2S)-2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
(2S)-2-ammonio-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoate
(2S)-2-azaniumyl-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoate
3-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-alanine
3-(3,4-dioxocyclohexa-1,5-dien-1-yl)-L-alanine
L-dopaquinone
o-Dopaquinone

Chemical Formula

C₉H₉NO₄

Average Molecular Mass

195.172 g/mol

Monoisotopic Mass

195.053 g/mol

CAS Registry Number

110810-88-3

IUPAC Name

2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

Traditional Name

2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

SMILES

NC(CC1=CC(=O)C(=O)C=C1)C(O)=O

InChI Identifier

InChI=1/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)

InChI Key

InChIKey=AHMIDUVKSGCHAU-UHFFFAOYNA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
O-benzoquinone
Quinone
Ketone
Cyclic ketone
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Cytoplasm
Extracellular

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

Solid

Appearance

White powder.

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	1.58 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.1	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	9.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.48 m³·mol⁻¹	ChemAxon
Polarizability	18.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fml-5900000000-3f77b48d5f42d8951324	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0udi-4910000000-dccd3d9d4cceeaf64aa7	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ufs-0900000000-d1c114d7f976c74c615f	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-1900000000-662d137e5426f439dc69	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9200000000-6dbb8ab9262bb219b883	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-af5c0b9a3a0913d69ab5	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-0900000000-f5ca0211f962a4918c7e	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-7900000000-1397cdd82f8d772a68f7	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udj-0900000000-2ca1383c9487e79be90a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ff0-0900000000-92f4bf729acf4be5b6bf	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00e9-8900000000-d3972df871a20993fe05	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-c319fd057861dc7d7ad4	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00e9-3900000000-b64033d6c2ec2ca4314b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-5900000000-cde5f7d52f36428ed06e	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View 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)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of DOPA-quinone is associated with Parkinson's disease.

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB39119

PubChem Compound ID

682

ChEMBL ID

Not Available

ChemSpider ID

662

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

L-Dopaquinone (T3D4967)

Structure for T3D4967: L-Dopaquinone