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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:32 UTC

HMDB ID

HMDB0001229

Secondary Accession Numbers

HMDB01229

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>
HMDB0001229

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₉H₉NO₄

Average Molecular Weight

195.1721

Monoisotopic Molecular Weight

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 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	147.004	31661259
DarkChem	[M-H]-	138.679	31661259
AllCCS	[M+H]+	142.477	32859911
AllCCS	[M-H]-	139.832	32859911
DeepCCS	[M+H]+	144.994	30932474
DeepCCS	[M-H]-	142.598	30932474
DeepCCS	[M-2H]-	175.826	30932474
DeepCCS	[M+Na]+	150.913	30932474
AllCCS	[M+H]+	142.5	32859911
AllCCS	[M+H-H2O]+	138.4	32859911
AllCCS	[M+NH4]+	146.3	32859911
AllCCS	[M+Na]+	147.4	32859911
AllCCS	[M-H]-	139.8	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	141.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.88 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7868 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.47 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	309.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	595.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	305.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	66.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	48.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	275.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	253.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	724.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	664.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	52.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	714.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	187.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	190.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	600.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	470.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	254.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dopaquinone	N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O	2992.9	Standard polar	33892256
Dopaquinone	N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O	1669.1	Standard non polar	33892256
Dopaquinone	N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O	2072.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dopaquinone,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(=O)C(=O)C=C1	2063.1	Semi standard non polar	33892256
Dopaquinone,1TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O	2136.6	Semi standard non polar	33892256
Dopaquinone,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O[Si](C)(C)C	2162.5	Semi standard non polar	33892256
Dopaquinone,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O[Si](C)(C)C	2039.3	Standard non polar	33892256
Dopaquinone,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O[Si](C)(C)C	3018.7	Standard polar	33892256
Dopaquinone,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O)[Si](C)(C)C	2268.6	Semi standard non polar	33892256
Dopaquinone,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O)[Si](C)(C)C	2106.1	Standard non polar	33892256
Dopaquinone,2TMS,isomer #2	C[Si](C)(C)N([C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O)[Si](C)(C)C	3121.6	Standard polar	33892256
Dopaquinone,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2276.6	Semi standard non polar	33892256
Dopaquinone,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2183.4	Standard non polar	33892256
Dopaquinone,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2949.5	Standard polar	33892256
Dopaquinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(=O)C(=O)C=C1	2328.9	Semi standard non polar	33892256
Dopaquinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O	2387.6	Semi standard non polar	33892256
Dopaquinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2642.8	Semi standard non polar	33892256
Dopaquinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2501.2	Standard non polar	33892256
Dopaquinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3149.8	Standard polar	33892256
Dopaquinone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2772.2	Semi standard non polar	33892256
Dopaquinone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2535.4	Standard non polar	33892256
Dopaquinone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC(=O)C(=O)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3226.8	Standard polar	33892256
Dopaquinone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2996.1	Semi standard non polar	33892256
Dopaquinone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2809.2	Standard non polar	33892256
Dopaquinone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3101.0	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Alkaptonuria		Not Available
Hawkinsinuria		Not Available
Tyrosinemia Type I		Not Available
Tyrosinemia, transient, of the newborn		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	19636438	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

DOPAQN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Land E J; Riley P A Spontaneous redox reactions of dopaquinone and the balance between the eumelanic and phaeomelanic pathways. Pigment cell research / sponsored by the European Society for Pigment Cell Research and the International Pigment Cell Society (2000), 13(4), 273-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:9873171 ]
Graham DG, Tiffany SM, Vogel FS: The toxicity of melanin precursors. J Invest Dermatol. 1978 Feb;70(2):113-6. [PubMed:413870 ]
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 ]
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 ]

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Reactions

DOPA + Oxygen → Dopaquinone + Water	details
L-Tyrosine + Oxygen → Dopaquinone + Water	details
DOPA + L-Tyrosine + Oxygen → Dopaquinone + DOPA + Water	details

Showing metabocard for Dopaquinone (HMDB0001229)

MOL for HMDB0001229 (Dopaquinone)

3D MOL for HMDB0001229 (Dopaquinone)

3D SDF for HMDB0001229 (Dopaquinone)

3D-SDF for HMDB0001229 (Dopaquinone)

PDB for HMDB0001229 (Dopaquinone)

3D PDB for HMDB0001229 (Dopaquinone)

SMILES for HMDB0001229 (Dopaquinone)

INCHI for HMDB0001229 (Dopaquinone)

Structure for HMDB0001229 (Dopaquinone)

3D Structure for HMDB0001229 (Dopaquinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions