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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:42 UTC

HMDB ID

HMDB0001430

Secondary Accession Numbers

HMDB01430

Metabolite Identification

Common Name

L-Dopachrome

Description

Dopachrome is a cyclization product of L-DOPA and is an intermediate in the biosynthesis of melanin. Dopaquinone has an ortho-quinone ring, which is known to be neurotoxic and highly reactive with many other compounds (PMID: 413870 ). Dopachrome spontaneously gives rise to 5,6-dihydroxyindole (DHI) or it can be enzymatically metabolized by dopachrome tautomerase to give 5,6-dihydroxyindole-2-carboxylic acid (DHICA). DHI and its oxidation products are also toxic to cells. Many Parkinson's patients are treated with L-DOPA. However, long-term treatment with L-DOPA may actually worsen symptoms or may 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


  Mrv1652303051804412D          

 14 15  0  0  0  0            999 V2000
 9997.5010 9998.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.501010000.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.932610000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.218110000.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2181 9999.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9326 9998.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.431710000.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6471 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6470 9999.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4317 9998.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9165 9999.5874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.7415 9999.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1540 9998.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.154110000.3018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 14  2  0  0  0  0
 12 13  1  0  0  0  0
  5  1  2  0  0  0  0
  4  2  2  0  0  0  0
  3  8  2  0  0  0  0
  6  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001430

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10H,1H2,(H,13,14)/t6-/m0/s1

> <INCHI_KEY>
VJNCICVKUHKIIV-LURJTMIESA-N

> <FORMULA>
C9H7NO4

> <MOLECULAR_WEIGHT>
193.158

> <EXACT_MASS>
193.037507709

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.478121868246767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-5,6-dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid

> <ALOGPS_LOGP>
0.22

> <JCHEM_LOGP>
-0.08718718499999992

> <ALOGPS_LOGS>
-1.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.0573667859171

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.668581054597647

> <JCHEM_PKA_STRONGEST_BASIC>
-8.82531687301901

> <JCHEM_POLAR_SURFACE_AREA>
83.47

> <JCHEM_REFRACTIVITY>
47.883700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-dopachrome

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-MAR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-MAR-18         0                                  
HETATM    1  O   UNK     0    8662.0028664.355   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8662.0028667.437   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8664.6748667.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.3408666.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.3408665.126   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8664.6748664.357   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8667.4738667.142   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8666.0088666.666   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.0088665.126   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.4738664.651   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.3778665.896   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.9178665.896   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8670.6878664.563   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8670.6888667.230   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    4                                                            
CONECT    3    4    8                                                       
CONECT    4    3    5    2                                                  
CONECT    5    4    6    1                                                  
CONECT    6    5    9                                                       
CONECT    7    8   11                                                       
CONECT    8    9    7    3                                                  
CONECT    9    8   10    6                                                  
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-L-Carboxy-2,3-dihydroindole-5,6-quinone	ChEBI
(2S)-2,3,5,6-Tetrahydro-5,6-dioxo-1H-indole-2-carboxylic acid	HMDB
(2S)-5,6-Dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid	HMDB
L-Dopachrome	HMDB

Chemical Formula

C₉H₇NO₄

Average Molecular Weight

193.158

Monoisotopic Molecular Weight

193.037507709

IUPAC Name

(2S)-5,6-dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid

Traditional Name

L-dopachrome

CAS Registry Number

89762-39-0

SMILES

OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1

InChI Identifier

InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10H,1H2,(H,13,14)/t6-/m0/s1

InChI Key

VJNCICVKUHKIIV-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
Indole or derivatives
Dihydroindole
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Vinylogous amide
Amino acid
Ketone
Cyclic ketone
Carboxylic acid
Secondary aliphatic amine
Enamine
Monocarboxylic acid or derivatives
Azacycle
Secondary amine
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Amine
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

dopachrome (CHEBI:15772 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001430)

Source

Endogenous

Endogenous (HMDB: HMDB0001430)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (PathBank: SMP0087328)
Eumelanin Biosynthesis (PathBank: SMP0121124)

Disease pathway

Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)

Drug action pathway

Disulfiram Action Pathway (PathBank: SMP0000429)

Role

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	11.9 g/L	ALOGPS
logP	0.22	ALOGPS
logP	-0.087	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	-8.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.47 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.88 m³·mol⁻¹	ChemAxon
Polarizability	17.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	145.348	31661259
DarkChem	[M-H]-	137.904	31661259
AllCCS	[M+H]+	141.31	32859911
AllCCS	[M-H]-	138.629	32859911
DeepCCS	[M+H]+	141.065	30932474
DeepCCS	[M-H]-	138.669	30932474
DeepCCS	[M-2H]-	171.937	30932474
DeepCCS	[M+Na]+	146.977	30932474
AllCCS	[M+H]+	141.3	32859911
AllCCS	[M+H-H2O]+	137.0	32859911
AllCCS	[M+NH4]+	145.3	32859911
AllCCS	[M+Na]+	146.4	32859911
AllCCS	[M-H]-	138.6	32859911
AllCCS	[M+Na-2H]-	138.8	32859911
AllCCS	[M+HCOO]-	139.0	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.	3.09 minutes	32390414
Predicted by Siyang on May 30, 2022	9.5982 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.61 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	210.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	785.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	302.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	67.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	51.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	250.3 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	271.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	545.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	610.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	88.2 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	906.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	171.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	667.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	245.2 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	291.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Dopachrome	OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1	3410.4	Standard polar	33892256
L-Dopachrome	OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1	1679.3	Standard non polar	33892256
L-Dopachrome	OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1	2079.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Dopachrome,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1	2148.2	Semi standard non polar	33892256
L-Dopachrome,1TMS,isomer #2	C[Si](C)(C)N1C2=CC(=O)C(=O)C=C2C[C@H]1C(=O)O	2208.2	Semi standard non polar	33892256
L-Dopachrome,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1[Si](C)(C)C	2204.9	Semi standard non polar	33892256
L-Dopachrome,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1[Si](C)(C)C	1933.8	Standard non polar	33892256
L-Dopachrome,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1[Si](C)(C)C	3214.0	Standard polar	33892256
L-Dopachrome,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1	2399.8	Semi standard non polar	33892256
L-Dopachrome,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C2=CC(=O)C(=O)C=C2C[C@H]1C(=O)O	2455.4	Semi standard non polar	33892256
L-Dopachrome,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1[Si](C)(C)C(C)(C)C	2665.8	Semi standard non polar	33892256
L-Dopachrome,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1[Si](C)(C)C(C)(C)C	2361.6	Standard non polar	33892256
L-Dopachrome,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1[Si](C)(C)C(C)(C)C	3349.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Dopachrome GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 10V, Positive-QTOF	splash10-002f-0900000000-7d241073b22105a8fd50	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 20V, Positive-QTOF	splash10-0002-0900000000-323f4bcd8528fb467c2b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 40V, Positive-QTOF	splash10-00ba-7900000000-13c63b10c546db28b452	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 10V, Negative-QTOF	splash10-0006-0900000000-7278b78e7703333d1049	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 20V, Negative-QTOF	splash10-006w-0900000000-37fa92b16a4a5557156c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 40V, Negative-QTOF	splash10-006w-2900000000-a811e0992f3245b7b855	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 10V, Negative-QTOF	splash10-0006-0900000000-becbc589150d5f7b8591	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 20V, Negative-QTOF	splash10-0002-0900000000-96e2a94dd742e6e1937c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 40V, Negative-QTOF	splash10-006w-1900000000-1956f467b1b38dab6842	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 10V, Positive-QTOF	splash10-0006-0900000000-ae6d437a06113eb43338	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 20V, Positive-QTOF	splash10-004m-0900000000-5329f1d5b80270050bbb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Dopachrome 40V, Positive-QTOF	splash10-006y-8900000000-bfc43ab0afc8b1b28daf	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

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

Not Available

Abnormal Concentrations

Not Available

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

FDB022618

KNApSAcK ID

Not Available

Chemspider ID

4573572

KEGG Compound ID

C01693

BioCyc ID

L-DOPACHROME

BiGG ID

Not Available

Wikipedia Link

Dopachrome

METLIN ID

Not Available

PubChem Compound

5459802

PDB ID

Not Available

ChEBI ID

15772

Food Biomarker Ontology

Not Available

VMH ID

L_DPCHRM

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Pak BJ, Li Q, Kerbel RS, Ben-David Y: TYRP2-mediated resistance to cis-diamminedichloroplatinum (II) in human melanoma cells is independent of tyrosinase and TYRP1 expression and melanin content. Melanoma Res. 2000 Oct;10(5):499-505. [PubMed:11095412 ]
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

Enzyme Details

2. Macrophage migration inhibitory factor

General function:: Involved in cell surface binding
Specific function:: Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
Gene Name:: MIF
Uniprot ID:: P14174
Molecular weight:: 12476.19

Reactions

L-Dopachrome → 5,6-Dihydroxyindole-2-carboxylic acid	details

Enzyme Details

3. L-dopachrome tautomerase

General function:: Involved in oxidoreductase activity
Specific function:: Involved in regulating eumelanin and phaeomelanin levels.
Gene Name:: DCT
Uniprot ID:: P40126
Molecular weight:: 62928.215

Reactions

L-Dopachrome → 5,6-Dihydroxyindole-2-carboxylic acid	details

Showing metabocard for L-Dopachrome (HMDB0001430)

MOL for HMDB0001430 (L-Dopachrome)

3D MOL for HMDB0001430 (L-Dopachrome)

3D SDF for HMDB0001430 (L-Dopachrome)

3D-SDF for HMDB0001430 (L-Dopachrome)

PDB for HMDB0001430 (L-Dopachrome)

3D PDB for HMDB0001430 (L-Dopachrome)

SMILES for HMDB0001430 (L-Dopachrome)

INCHI for HMDB0001430 (L-Dopachrome)

Structure for HMDB0001430 (L-Dopachrome)

3D Structure for HMDB0001430 (L-Dopachrome)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions

Reactions