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Showing metabocard for Leucodopachrome (HMDB0004067)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 10:14:47 UTC
Update Date2023-02-21 17:16:53 UTC
HMDB IDHMDB0004067
Secondary Accession Numbers
  • HMDB0006340
  • HMDB04067
  • HMDB06340
Metabolite Identification
Common NameLeucodopachrome
DescriptionLeucodopachrome is an indolic intermediate in the melanogenesis pathway, the non-enzymatic product of dopaquinone through cyclization in a reaction whose operation is determined by a pH greater than 4 (melanin synthesis in human pigment cell lysates is maximal at pH 6.8). Leucodopachrome participates in redox exchange with dopaquinone to give the eumelanin precursor dopachrome plus DOPA. Dopaquinone (the quinone intermediate resulting from tyrosinase-mediated oxidation of tyrosine, monophenol dihydroxyphenylalanine:oxygen oxidoreductase, EC 1.14.18.1) could be a toxic metabolite in melanin biosynthesis (PMID: 6807981 , 1445949 , 413870 , 11461115 , 11171088 , 12755639 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004067 (Leucodopachrome)

  Mrv0541 02231219522D          

 14 15  0  0  1  0            999 V2000
   31.4505  -10.6106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8073   -9.0711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8073  -10.7211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4505   -9.1816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7314   -9.2322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2129   -9.8961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.7314  -10.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0379   -9.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5218   -9.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5218  -10.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508   -9.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -10.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364   -9.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364  -10.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  6  0  0  0
  7 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  2  0  0  0  0
M  END
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3D MOL for HMDB0004067 (Leucodopachrome)

HMDB0004067
     RDKit          3D
Leucodopachrome
 23 24  0  0  0  0  0  0  0  0999 V2000
    3.8198   -0.5912    1.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -0.1081    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1921    0.6070   -0.7213 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9277   -0.2234   -0.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2008    1.0979   -0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    0.6700   -0.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4352    1.2270   -0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782    0.5230   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8346    1.0505   -0.4681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810   -0.7321    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7679   -1.4050    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -1.2821    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940   -0.5782    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1490   -0.9838    0.6604 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6071    0.1658   -1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194   -0.6956   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615    1.6624    0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3777    1.6899   -1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533    2.1949   -0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9524    1.9593   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7003   -2.3166    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3305   -2.2642    1.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5047   -1.6673    1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14  4  1  0
 13  6  1  0
  3 15  1  0
  4 16  1  6
  5 17  1  0
  5 18  1  0
  7 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
 14 23  1  0
M  END
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3D SDF for HMDB0004067 (Leucodopachrome)

  Mrv0541 02231219522D          

 14 15  0  0  1  0            999 V2000
   31.4505  -10.6106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8073   -9.0711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8073  -10.7211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4505   -9.1816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7314   -9.2322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2129   -9.8961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.7314  -10.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0379   -9.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5218   -9.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5218  -10.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508   -9.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -10.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364   -9.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364  -10.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  6  0  0  0
  7 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004067

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10-12H,1H2,(H,13,14)/t6-/m0/s1

> <INCHI_KEY>
JDWYRSDDJVCWPB-LURJTMIESA-N

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.1721

> <EXACT_MASS>
195.053157781

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
18.44620378439588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
-0.9458621457375678

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.706612328861542

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.159346987053667

> <JCHEM_PKA_STRONGEST_BASIC>
1.9881428552886438

> <JCHEM_POLAR_SURFACE_AREA>
89.78999999999999

> <JCHEM_REFRACTIVITY>
49.35310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclodopa

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0004067 (Leucodopachrome)

HMDB0004067
     RDKit          3D
Leucodopachrome
 23 24  0  0  0  0  0  0  0  0999 V2000
    3.8198   -0.5912    1.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -0.1081    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1921    0.6070   -0.7213 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9277   -0.2234   -0.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2008    1.0979   -0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    0.6700   -0.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4352    1.2270   -0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782    0.5230   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8346    1.0505   -0.4681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810   -0.7321    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7679   -1.4050    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -1.2821    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940   -0.5782    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1490   -0.9838    0.6604 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6071    0.1658   -1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194   -0.6956   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615    1.6624    0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3777    1.6899   -1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533    2.1949   -0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9524    1.9593   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7003   -2.3166    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3305   -2.2642    1.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5047   -1.6673    1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14  4  1  0
 13  6  1  0
  3 15  1  0
  4 16  1  6
  5 17  1  0
  5 18  1  0
  7 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
 14 23  1  0
M  END
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PDB for HMDB0004067 (Leucodopachrome)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      58.708 -19.806   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      50.040 -16.933   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      50.040 -20.013   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      58.708 -17.139   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      55.499 -17.233   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      56.397 -18.473   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      55.499 -19.712   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      57.937 -18.473   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      51.374 -17.703   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      51.374 -19.243   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      54.041 -17.703   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      54.041 -19.243   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      52.708 -16.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      52.708 -20.013   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    8                                                            
CONECT    5    6   11                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6   12                                                       
CONECT    8    1    4    6                                                  
CONECT    9    2   10   13                                                  
CONECT   10    3    9   14                                                  
CONECT   11    5   12   13                                                  
CONECT   12    7   11   14                                                  
CONECT   13    9   11                                                       
CONECT   14   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for HMDB0004067 (Leucodopachrome)

COMPND    HMDB0004067
HETATM    1  O1  UNL     1       3.820  -0.591   1.160  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.337  -0.108   0.125  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.192   0.607  -0.721  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.928  -0.223  -0.296  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.201   1.098  -0.297  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.213   0.670  -0.157  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.435   1.227  -0.463  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.578   0.523  -0.175  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.835   1.050  -0.468  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.581  -0.732   0.413  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.768  -1.405   0.684  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.357  -1.282   0.715  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.194  -0.578   0.428  1.00  0.00           C  
HETATM   14  N1  UNL     1       1.149  -0.984   0.660  1.00  0.00           N  
HETATM   15  H1  UNL     1       4.607   0.166  -1.549  1.00  0.00           H  
HETATM   16  H2  UNL     1       1.819  -0.696  -1.300  1.00  0.00           H  
HETATM   17  H3  UNL     1       1.462   1.662   0.629  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.378   1.690  -1.217  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.453   2.195  -0.917  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.952   1.959  -0.898  1.00  0.00           H  
HETATM   21  H7  UNL     1      -3.700  -2.317   1.114  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.331  -2.264   1.177  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.505  -1.667   1.353  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5   14   16
CONECT    5    6   17   18
CONECT    6    7    7   13
CONECT    7    8   19
CONECT    8    9   10   10
CONECT    9   20
CONECT   10   11   12
CONECT   11   21
CONECT   12   13   13   22
CONECT   13   14
CONECT   14   23
END
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SMILES for HMDB0004067 (Leucodopachrome)

OC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N1
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INCHI for HMDB0004067 (Leucodopachrome)

InChI=1S/C9H9NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10-12H,1H2,(H,13,14)/t6-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(S)-2-Carboxy-5,6-dihydroxyindolineChEBI
(S)-5,6-Dihydroxyindoline-2-carboxylic acidChEBI
Cyclo-dopaChEBI
CyclodopaChEBI
L-2-Carboxy-2,3-dihydro-5,6-dihydroxyindoleChEBI
LeukodopachromeChEBI
(S)-5,6-Dihydroxyindoline-2-carboxylateGenerator
2,3-dihydro-5,6-Dihydroxyindole-2-carboxylateHMDB, MeSH
2-Carboxy-2,3-dihydro-5,6-dihydroxyindoleHMDB
Chemical FormulaC9H9NO4
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
IUPAC Name(2S)-5,6-dihydroxy-2,3-dihydro-1H-indole-2-carboxylic acid
Traditional Namecyclodopa
CAS Registry Number18766-67-1
SMILES
OC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N1
InChI Identifier
InChI=1S/C9H9NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10-12H,1H2,(H,13,14)/t6-/m0/s1
InChI KeyJDWYRSDDJVCWPB-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolecarboxylic acids and derivatives
Direct ParentIndolecarboxylic acids
Alternative Parents
Substituents
  • Indolecarboxylic acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Dihydroindole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Secondary aliphatic/aromatic amine
  • Aralkylamine
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.037Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCCD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIleal Crohn's disease details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023297
KNApSAcK IDC00051835
Chemspider ID141655
KEGG Compound IDC05604
BioCyc IDCPD-8652
BiGG ID46110
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound161255
PDB IDNot Available
ChEBI ID60872
Food Biomarker OntologyNot Available
VMH ID2C23DH56DHOXIN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Canovas FG, Garcia-Carmona F, Sanchez JV, Pastor JL, Teruel JA: The role of pH in the melanin biosynthesis pathway. J Biol Chem. 1982 Aug 10;257(15):8738-44. [PubMed:6807981 ]
  2. Rodriguez-Lopez JN, Banon-Arnao M, Martinez-Ortiz F, Tudela J, Acosta M, Varon R, Garcia-Canovas F: Catalytic oxidation of 2,4,5-trihydroxyphenylalanine by tyrosinase: identification and evolution of intermediates. Biochim Biophys Acta. 1992 Nov 20;1160(2):221-8. [PubMed:1445949 ]
  3. Graham DG, Tiffany SM, Vogel FS: The toxicity of melanin precursors. J Invest Dermatol. 1978 Feb;70(2):113-6. [PubMed:413870 ]
  4. Ancans J, Tobin DJ, Hoogduijn MJ, Smit NP, Wakamatsu K, Thody AJ: Melanosomal pH controls rate of melanogenesis, eumelanin/phaeomelanin ratio and melanosome maturation in melanocytes and melanoma cells. Exp Cell Res. 2001 Aug 1;268(1):26-35. [PubMed:11461115 ]
  5. Olivares C, Jimenez-Cervantes C, Lozano JA, Solano F, Garcia-Borron JC: The 5,6-dihydroxyindole-2-carboxylic acid (DHICA) oxidase activity of human tyrosinase. Biochem J. 2001 Feb 15;354(Pt 1):131-9. [PubMed:11171088 ]
  6. Land EJ, Ramsden CA, Riley PA: Tyrosinase autoactivation and the chemistry of ortho-quinone amines. Acc Chem Res. 2003 May;36(5):300-8. [PubMed:12755639 ]