Showing metabocard for L-Dopachrome (MMDBc0047930)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:16:17 UTC
Update Date2024-04-30 20:32:50 UTC
Metabolite IDMMDBc0047930
Metabolite Identification
Common NameL-Dopachrome
DescriptionDopachrome 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fecac11c150>


  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
Download

3D MOL for #<Metabolite:0x00007fecac11c150>

HMDB0001430
     RDKit          3D
L-Dopachrome
 21 22  0  0  0  0  0  0  0  0999 V2000
    4.0168    1.5301   -0.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9703    0.8703   -0.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6681    1.2801   -0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5729    0.5637   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514    0.7277   -0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5698   -0.1153    0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9210   -0.5326   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -1.7319   -0.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8579    0.4698   -0.4347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865   -1.2463    0.4004 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -0.6849    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7983   -1.1232    0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0507   -0.3904    0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1432   -0.7942    1.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364    2.2242   -1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9418    0.2893   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1667    1.7903   -0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6393    0.4665    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5758    0.7202    0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834   -2.2558    0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217   -2.0577    1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13  2  1  0
 11  4  1  0
  3 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  1
  9 19  1  0
 10 20  1  0
 12 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fecac11c150>


  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>
MMDBc0047930

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007fecac11c150>

HMDB0001430
     RDKit          3D
L-Dopachrome
 21 22  0  0  0  0  0  0  0  0999 V2000
    4.0168    1.5301   -0.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9703    0.8703   -0.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6681    1.2801   -0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5729    0.5637   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514    0.7277   -0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5698   -0.1153    0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9210   -0.5326   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -1.7319   -0.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8579    0.4698   -0.4347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865   -1.2463    0.4004 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -0.6849    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7983   -1.1232    0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0507   -0.3904    0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1432   -0.7942    1.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6364    2.2242   -1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9418    0.2893   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1667    1.7903   -0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6393    0.4665    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5758    0.7202    0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834   -2.2558    0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217   -2.0577    1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13  2  1  0
 11  4  1  0
  3 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  1
  9 19  1  0
 10 20  1  0
 12 21  1  0
M  END
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PDB for #<Metabolite:0x00007fecac11c150>

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
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3D PDB for #<Metabolite:0x00007fecac11c150>

COMPND    HMDB0001430
HETATM    1  O1  UNL     1       4.017   1.530  -0.253  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.970   0.870  -0.083  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.668   1.280  -0.594  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.573   0.564  -0.401  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.851   0.728  -0.793  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.570  -0.115   0.218  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.921  -0.533  -0.226  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.228  -1.732  -0.412  1.00  0.00           O  
HETATM    9  O3  UNL     1      -3.858   0.470  -0.435  1.00  0.00           O  
HETATM   10  N1  UNL     1      -0.686  -1.246   0.400  1.00  0.00           N  
HETATM   11  C7  UNL     1       0.643  -0.685   0.346  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.798  -1.123   0.843  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.051  -0.390   0.673  1.00  0.00           C  
HETATM   14  O4  UNL     1       4.143  -0.794   1.137  1.00  0.00           O  
HETATM   15  H1  UNL     1       1.636   2.224  -1.155  1.00  0.00           H  
HETATM   16  H2  UNL     1      -0.942   0.289  -1.818  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.167   1.790  -0.777  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.639   0.467   1.160  1.00  0.00           H  
HETATM   19  H5  UNL     1      -4.576   0.720   0.230  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.883  -2.256   0.543  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.822  -2.058   1.396  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   15
CONECT    4    5   11
CONECT    5    6   16   17
CONECT    6    7   10   18
CONECT    7    8    8    9
CONECT    9   19
CONECT   10   11   20
CONECT   11   12   12
CONECT   12   13   21
CONECT   13   14   14
END
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SMILES for #<Metabolite:0x00007fecac11c150>

OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1
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INCHI for #<Metabolite:0x00007fecac11c150>

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
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Synonyms
ValueSource
2-L-Carboxy-2,3-dihydroindole-5,6-quinoneChEBI
(2S)-2,3,5,6-Tetrahydro-5,6-dioxo-1H-indole-2-carboxylic acidHMDB
(2S)-5,6-Dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acidHMDB
L-DopachromeHMDB
Molecular FormulaC9H7NO4
Average Mass193.158
Monoisotopic Mass193.037507709
IUPAC Name(2S)-5,6-dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid
Traditional NameL-dopachrome
CAS Registry Number89762-39-0
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 KeyVJNCICVKUHKIIV-LURJTMIESA-N