MiMeDB: Showing metabocard for Dopaquinone (MMDBc0048287)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:55:42 UTC

Update Date

2024-04-30 20:36:21 UTC

Metabolite ID

MMDBc0048287

Metabolite Identification

Common Name

Dopaquinone

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 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

ChEBI
  Mrv1652309042000192D          

 14 14  0  0  1  0            999 V2000
    7.7084   -2.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4245   -3.0214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9924   -3.0016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7310   -1.7673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9699   -3.8291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2763   -2.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5520   -2.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5520   -3.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7972   -4.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1179   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727   -2.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937   -4.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1323   -2.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4177   -2.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  1  2  0  0  0  0
  3  5  1  1  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
 11  7  2  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 12 10  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048287

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/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)/t6-/m0/s1

> <INCHI_KEY>
AHMIDUVKSGCHAU-LURJTMIESA-N

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.1721

> <EXACT_MASS>
195.053157781

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.058114570835116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

> <ALOGPS_LOGP>
-1.86

> <JCHEM_LOGP>
-2.0996093301828904

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8696975640830837

> <JCHEM_PKA_STRONGEST_BASIC>
9.06375153550613

> <JCHEM_POLAR_SURFACE_AREA>
97.46000000000001

> <JCHEM_REFRACTIVITY>
49.478100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dopaquinone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      14.389  -4.843   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.726  -5.640   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.052  -5.603   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      14.431  -3.299   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      13.010  -7.148   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.716  -4.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.364  -5.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.364  -7.095   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.955  -7.790   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.687  -6.990   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.096  -4.739   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.335  -7.722   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.714  -5.418   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.380  -4.648   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1    5    6                                                  
CONECT    4    1                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   13   12                                                  
CONECT   11    7   13                                                       
CONECT   12   10                                                            
CONECT   13   10   11   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
(S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoate	ChEBI
(S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid	Generator
O-Dopaquinone	HMDB
4-(2-Carboxy-2-aminoethyl)-1,2-benzoquinone	HMDB
Dopaquinone, (S)-isomer	HMDB
L-Dopaquinone	HMDB

Molecular Formula

C₉H₉NO₄

Average Mass

195.1721

Monoisotopic Mass

195.053157781

IUPAC Name

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

Traditional Name

dopaquinone

CAS Registry Number

4430-97-1

SMILES

N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O

InChI Identifier

InChI=1S/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)/t6-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

amino acid zwitterion (CHEBI:57924 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	18.06 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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	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	splash10-00di-9570000000-5d835cfbd2b202044cb7	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ufs-0900000000-093c511b443d87916930	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-1900000000-fc3bdef4314080b351c1	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-9200000000-07d0c6318c984ef80e41	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-7481c7c6fe6294da272c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-0900000000-04347396e1171463fb62	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-7900000000-13ce3640966908fffe55	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-c319fd057861dc7d7ad4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00e9-3900000000-b64033d6c2ec2ca4314b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-5900000000-cde5f7d52f36428ed06e	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udj-0900000000-2ca1383c9487e79be90a	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ff0-0900000000-92f4bf729acf4be5b6bf	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00e9-8900000000-d3972df871a20993fe05	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191760	Tyrosinase	Unknown	P14679	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000813	Dopaquinone	Leucodopachrome	Not Available	Dopaquinone Isomerase 1	VMH	5294951
MMDBr0002299	L-Dopa	Dopaquinone	Tyrosinase	Tyrosine:Dopa Oxidase (Dopaquinone Producing 2)	VMH	5294951
MMDBr0004120	L-Cysteine	5-S-Cysteinyldopa	Not Available	RE1915C	VMH	8819121 8931873
MMDBr0004121	Dopaquinone	5-S-Glutathionyl-L-Dopa	Not Available	Glutathione Transferase	VMH	10903891
MMDBr0004122	Dopaquinone	5-S-Glutathionyl-L-Dopa	Glutathione s-transferase kappa 1	Glutathione Transferase	VMH	10903891
MMDBr0004123	5-S-Cysteinyldopa	L-Dopa	Not Available	RE1917C	VMH	10903891
MMDBr0010438	Oxygen	Dopaquinone	Tyrosinase	L-Tyrosine, L-Dopa:Oxygen Oxidoreductase	VMH; KEGG	30371894
MMDBr0010439	Leucodopachrome	L-Dopa	Not Available	HMR_6876	VMH; KEGG	30371894
MMDBr0015330	L-Dopa	Water	Polyphenol oxidase 1	Oxidation	RHEA	34755880
MMDBr0017881	L-Tyrosine	Water	Polyphenol oxidase 1	Oxidation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Eukaryota/Fungi	Basidiomycota	9	Human feces
Eukaryota/Fungi	Ascomycota	7	Human feces
Bacteria	Proteobacteria	1
Bacteria	Actinobacteria	2
Bacteria/NULL	Actinobacteria	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified	Children (1-13 years old)	Both	Normal	HMDB	19636438

External Links

HMDB ID

HMDB0001229

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022501

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16852

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Graham DG, Tiffany SM, Vogel FS: The toxicity of melanin precursors. J Invest Dermatol. 1978 Feb;70(2):113-6. doi: 10.1111/1523-1747.ep12541249. [PubMed:413870 ]
Rorsman H, Tegner E: Biochemical observations in UV-induced pigmentation. Photodermatol. 1988 Feb;5(1):30-8. [PubMed:3281148 ]
Tsukamoto K, Furue M, Sato Y, Takayama O, Akasu R, Ohtake N, Wakamatsu K, Ito S, Tamaki K, Shimada S: Generalized melanosis in metastatic malignant melanoma: the possible role of DOPAquinone metabolites. Dermatology. 1998;197(4):338-42. doi: 10.1159/000018028. [PubMed:9873171 ]
Kostrzewa RM, Kostrzewa JP, Brus R: Neuroprotective and neurotoxic roles of levodopa (L-DOPA) in neurodegenerative disorders relating to Parkinson's disease. Amino Acids. 2002;23(1-3):57-63. doi: 10.1007/s00726-001-0110-x. [PubMed:12373519 ]
Hattoria N, Wanga M, Taka H, Fujimura T, Yoritaka A, Kubo S, Mochizuki H: Toxic effects of dopamine metabolism in Parkinson's disease. Parkinsonism Relat Disord. 2009 Jan;15 Suppl 1:S35-8. doi: 10.1016/S1353-8020(09)70010-0. [PubMed:19131041 ]

Showing metabocard for Dopaquinone (MMDBc0048287)

MOL for #<Metabolite:0x00007fa4e025b958>

3D MOL for #<Metabolite:0x00007fa4e025b958>

3D SDF for #<Metabolite:0x00007fa4e025b958>

3D-SDF for #<Metabolite:0x00007fa4e025b958>

PDB for #<Metabolite:0x00007fa4e025b958>

3D PDB for #<Metabolite:0x00007fa4e025b958>

SMILES for #<Metabolite:0x00007fa4e025b958>

INCHI for #<Metabolite:0x00007fa4e025b958>

Structure for #<Metabolite:0x00007fa4e025b958>

3D Structure for #<Metabolite:0x00007fa4e025b958>