Showing metabocard for Dopaquinone (MMDBc0048287)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 21:55:42 UTC
Update Date2024-10-09 19:37:18 UTC
Metabolite IDMMDBc0048287
Metabolite Identification
Common NameDopaquinone
DescriptionDopaquinone, 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f925142a730>

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
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3D MOL for #<Metabolite:0x00007f925142a730>

HMDB0001229
     RDKit          3D
Dopaquinone
 23 23  0  0  0  0  0  0  0  0999 V2000
   -1.8238   -1.4433    0.4865 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -0.0009    0.5539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7513    0.6463    1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390    0.4249    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356    1.4739    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5260    1.2803   -0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120    2.2320   -1.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601   -0.0673   -0.7437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807   -0.2689   -1.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2573   -1.1579   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -0.9129    0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    0.4733   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110    1.7124   -0.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2944   -0.3435   -1.9251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4253   -1.8480   -0.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093   -1.8549    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8719    0.2024    1.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9982    1.7446    1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7200    0.3073    2.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8283    2.4664    0.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5980   -2.1767   -0.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4853   -1.7419    0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6813   -1.1474   -2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
 11  4  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  5 20  1  0
 10 21  1  0
 11 22  1  0
 14 23  1  0
M  END
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3D SDF for #<Metabolite:0x00007f925142a730>

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

$$$$
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3D-SDF for #<Metabolite:0x00007f925142a730>

HMDB0001229
     RDKit          3D
Dopaquinone
 23 23  0  0  0  0  0  0  0  0999 V2000
   -1.8238   -1.4433    0.4865 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -0.0009    0.5539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7513    0.6463    1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390    0.4249    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356    1.4739    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5260    1.2803   -0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120    2.2320   -1.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601   -0.0673   -0.7437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807   -0.2689   -1.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2573   -1.1579   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -0.9129    0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    0.4733   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110    1.7124   -0.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2944   -0.3435   -1.9251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4253   -1.8480   -0.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093   -1.8549    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8719    0.2024    1.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9982    1.7446    1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7200    0.3073    2.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8283    2.4664    0.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5980   -2.1767   -0.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4853   -1.7419    0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6813   -1.1474   -2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
 11  4  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  5 20  1  0
 10 21  1  0
 11 22  1  0
 14 23  1  0
M  END
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PDB for #<Metabolite:0x00007f925142a730>

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
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3D PDB for #<Metabolite:0x00007f925142a730>

COMPND    HMDB0001229
HETATM    1  N1  UNL     1      -1.824  -1.443   0.486  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.929  -0.001   0.554  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.751   0.646   1.187  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.539   0.425   0.531  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.236   1.474   0.062  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.526   1.280  -0.597  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.212   2.232  -1.051  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.060  -0.067  -0.744  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.181  -0.269  -1.312  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.257  -1.158  -0.214  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.079  -0.913   0.380  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.186   0.473  -0.828  1.00  0.00           C  
HETATM   13  O3  UNL     1      -2.311   1.712  -0.990  1.00  0.00           O  
HETATM   14  O4  UNL     1      -2.294  -0.344  -1.925  1.00  0.00           O  
HETATM   15  H1  UNL     1      -2.425  -1.848  -0.264  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.009  -1.855   1.428  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.872   0.202   1.120  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.998   1.745   1.278  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.720   0.307   2.265  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.828   2.466   0.178  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.598  -2.177  -0.292  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.485  -1.742   0.779  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.681  -1.147  -2.032  1.00  0.00           H  
CONECT    1    2   15   16
CONECT    2    3   12   17
CONECT    3    4   18   19
CONECT    4    5    5   11
CONECT    5    6   20
CONECT    6    7    7    8
CONECT    8    9    9   10
CONECT   10   11   11   21
CONECT   11   22
CONECT   12   13   13   14
CONECT   14   23
END
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SMILES for #<Metabolite:0x00007f925142a730>

N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O
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INCHI for #<Metabolite:0x00007f925142a730>

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
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Synonyms
ValueSource
(S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoateChEBI
(S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acidGenerator
O-DopaquinoneHMDB
4-(2-Carboxy-2-aminoethyl)-1,2-benzoquinoneHMDB
Dopaquinone, (S)-isomerHMDB
L-DopaquinoneHMDB
Molecular FormulaC9H9NO4
Average Mass195.1721
Monoisotopic Mass195.053157781
IUPAC Name(2S)-2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
Traditional Namedopaquinone
CAS Registry Number4430-97-1
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 KeyAHMIDUVKSGCHAU-LURJTMIESA-N