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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 10:15:22 UTC

Update Date

2021-10-13 04:42:58 UTC

HMDB ID

HMDB0004068

Secondary Accession Numbers

HMDB04068

Metabolite Identification

Common Name

Melanin

Description

Dermal melanin is produced by melanocytes, which are found in the stratum basale of the epidermis. Although human beings generally possess a similar concentration of melanocytes in their skin, the melanocytes in some individuals and races more frequently or less frequently express the melanin-producing genes, thereby conferring a greater or lesser concentration of skin melanin. Some individual animals and humans have no or very little melanin in their bodies, which is a condition known as albinism. Higher eumelanin levels also can be a disadvantage, however, beyond a higher disposition toward vitamin D deficiency. Dark skin is a complicating factor in the laser removal of port-wine stains. Effective in treating fair skin, lasers generally are less successful in removing port-wine stains in Asians and people of African descent. Higher concentrations of melanin in darker-skinned individuals simply diffuse and absorb the laser radiation, inhibiting light absorption by the targeted tissue. Melanin similarly can complicate laser treatment of other dermatological conditions in people with darker skin. Under the microscope melanin is brown, non-refractile and finely granular with individual granules having a diameter of less than 800 nanometers. This differentiates melanin from common blood breakdown pigments which are larger, chunky and refractile and range in color from green to yellow or red-brown. In heavily pigmented lesions, dense aggregates of melanin can obscure histologic detail. A dilute solution of potassium permanganate is an effective melanin bleach. Pigments causing darkness in skin, hair, feathers, etc. They are irregular polymeric structures and are divided into three groups: allomelanins in the plant kingdom and eumelanins and phaeomelanins in the animal kingdom. Because melanin is an aggregate of smaller component molecules, there are a number of different types of melanin with differing proportions and bonding patterns of these component molecules. Both pheomelanin and eumelanin are found in human skin and hair, but eumelanin is the most abundant melanin in humans, as well as the form most likely to be deficient in albinism. Freckles and moles are formed where there is a localized concentration of melanin in the skin. They are highly associated with pale skin. Melanin is a biopolymer and a neuropeptide. In the early 1970s, John McGinness, Peter Corry, and Peter Proctor reported that melanin is a high-conductivity organic semiconductor (Science, vol 183, 853-855 (1974)). Studies revealed that melanin acted as a voltage-controlled solid-state threshold switch. Further, it emitting a flash of light electroluminescence when it switched.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0004068
     RDKit          3D
Melanin
 34 38  0  0  0  0  0  0  0  0999 V2000
    4.9930    0.0487   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5781   -0.3062   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1536   -1.4651   -0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0817   -2.1818   -1.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227   -1.7807   -1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -2.7913   -1.7167 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009   -0.9193   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4591   -1.1204   -0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821   -2.0651   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837   -1.7022   -0.9792 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176   -0.5511   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.3047    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0042   -0.0396    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565    1.4434    0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0565    2.1850    1.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    1.7736    1.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250    2.7807    1.7048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    0.9150    0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4827    1.1221    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2868    2.0720    1.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888    1.7145    0.9815 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    0.5603    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220    0.1995    0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -0.2012   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1488    1.1436   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6095   -0.4643   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3219   -0.2590    0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -2.9229   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4138   -2.2332   -1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4407    0.3681   -0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6436    0.3763    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1575   -1.1561    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277    2.9214    1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240    2.2306    1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 24  2  0
 22  2  2  0
 23  7  2  0
 24  8  1  0
 24 11  1  0
 23 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 20 33  1  0
 21 34  1  0
M  END

  Mrv0541 02231219522D          

 24 28  0  0  0  0            999 V2000
   29.5349  -11.1778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9107  -15.3772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5479  -12.8676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8976  -13.6874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7110  -11.5657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7345  -14.9893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4472  -16.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9983  -10.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2509  -11.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1946  -14.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2576  -12.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1880  -14.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7095  -14.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7361  -11.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9951  -11.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4504  -15.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4372  -13.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0083  -12.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7228  -12.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7228  -14.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4372  -12.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0083  -13.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4003  -14.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0452  -12.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2 10  2  0  0  0  0
  3 11  2  0  0  0  0
  4 12  2  0  0  0  0
  5 14  1  0  0  0  0
  5 24  1  0  0  0  0
  6 13  1  0  0  0  0
  6 23  1  0  0  0  0
  7 16  1  0  0  0  0
  8 15  1  0  0  0  0
  9 11  1  0  0  0  0
  9 15  1  0  0  0  0
 10 12  1  0  0  0  0
 10 16  1  0  0  0  0
 11 18  1  0  0  0  0
 12 17  1  0  0  0  0
 13 16  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  2  0  0  0  0
 17 21  1  0  0  0  0
 18 19  2  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 24  2  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004068

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2NC=C3C2=C(C2=CNC4=C(C)C(=O)C(=O)C3=C24)C(=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H10N2O4/c1-5-13-9-7(3-19-13)12-10-8(11(9)17(23)15(5)21)4-20-14(10)6(2)16(22)18(12)24/h3-4,19-20H,1-2H3

> <INCHI_KEY>
XUMBMVFBXHLACL-UHFFFAOYSA-N

> <FORMULA>
C18H10N2O4

> <MOLECULAR_WEIGHT>
318.283

> <EXACT_MASS>
318.064056818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.773272751291998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,14-dimethyl-4,12-diazapentacyclo[8.6.1.1²,⁵.0¹³,¹⁷.0⁹,¹⁸]octadeca-1(17),2,5,9(18),10,13-hexaene-7,8,15,16-tetrone

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
-0.2678974366666661

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.441299405325541

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.645386059348876

> <JCHEM_PKA_STRONGEST_BASIC>
1.335042551550563

> <JCHEM_POLAR_SURFACE_AREA>
92.34

> <JCHEM_REFRACTIVITY>
88.2778

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melanin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004068
     RDKit          3D
Melanin
 34 38  0  0  0  0  0  0  0  0999 V2000
    4.9930    0.0487   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5781   -0.3062   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1536   -1.4651   -0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0817   -2.1818   -1.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227   -1.7807   -1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -2.7913   -1.7167 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009   -0.9193   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4591   -1.1204   -0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821   -2.0651   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837   -1.7022   -0.9792 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176   -0.5511   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.3047    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0042   -0.0396    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565    1.4434    0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0565    2.1850    1.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    1.7736    1.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250    2.7807    1.7048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    0.9150    0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4827    1.1221    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2868    2.0720    1.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888    1.7145    0.9815 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    0.5603    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220    0.1995    0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -0.2012   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1488    1.1436   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6095   -0.4643   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3219   -0.2590    0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -2.9229   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4138   -2.2332   -1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4407    0.3681   -0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6436    0.3763    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1575   -1.1561    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277    2.9214    1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240    2.2306    1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 24  2  0
 22  2  2  0
 23  7  2  0
 24  8  1  0
 24 11  1  0
 23 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 20 33  1  0
 21 34  1  0
M  END

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      55.132 -20.865   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      63.300 -28.704   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      55.156 -24.020   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      63.276 -25.550   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      61.061 -21.589   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      57.371 -27.980   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      60.568 -30.281   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      57.863 -19.288   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      56.468 -21.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      61.963 -27.939   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      56.481 -23.234   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      61.951 -26.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      59.191 -27.929   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      59.241 -21.641   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      57.858 -20.828   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      60.574 -28.741   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      60.549 -25.555   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      57.882 -24.015   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      59.216 -23.245   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      59.216 -26.325   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      60.549 -24.015   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      57.882 -25.555   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      56.747 -26.582   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      61.684 -22.987   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   14   24                                                       
CONECT    6   13   23                                                       
CONECT    7   16                                                            
CONECT    8   15                                                            
CONECT    9    1   11   15                                                  
CONECT   10    2   12   16                                                  
CONECT   11    3    9   18                                                  
CONECT   12    4   10   17                                                  
CONECT   13    6   16   20                                                  
CONECT   14    5   15   19                                                  
CONECT   15    8    9   14                                                  
CONECT   16    7   10   13                                                  
CONECT   17   12   20   21                                                  
CONECT   18   11   19   22                                                  
CONECT   19   14   18   21                                                  
CONECT   20   13   17   22                                                  
CONECT   21   17   19   24                                                  
CONECT   22   18   20   23                                                  
CONECT   23    6   22                                                       
CONECT   24    5   21                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0004068
HETATM    1  C1  UNL     1       4.993   0.049  -0.072  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.578  -0.306  -0.258  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.154  -1.465  -0.950  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.082  -2.182  -1.401  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.823  -1.781  -1.114  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.450  -2.791  -1.717  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.901  -0.919  -0.575  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.459  -1.120  -0.670  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.282  -2.065  -1.224  1.00  0.00           C  
HETATM   10  N1  UNL     1      -2.584  -1.702  -0.979  1.00  0.00           N  
HETATM   11  C8  UNL     1      -2.618  -0.551  -0.283  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.582   0.305   0.252  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.004  -0.040   0.073  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.156   1.443   0.932  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.056   2.185   1.397  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.809   1.774   1.104  1.00  0.00           C  
HETATM   17  O4  UNL     1      -1.425   2.781   1.705  1.00  0.00           O  
HETATM   18  C13 UNL     1      -0.877   0.915   0.567  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.483   1.122   0.666  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.287   2.072   1.223  1.00  0.00           C  
HETATM   21  N2  UNL     1       2.589   1.715   0.982  1.00  0.00           N  
HETATM   22  C16 UNL     1       2.630   0.560   0.284  1.00  0.00           C  
HETATM   23  C17 UNL     1       1.322   0.199   0.092  1.00  0.00           C  
HETATM   24  C18 UNL     1      -1.312  -0.201  -0.098  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.149   1.144  -0.220  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.610  -0.464  -0.848  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.322  -0.259   0.958  1.00  0.00           H  
HETATM   28  H4  UNL     1      -0.901  -2.923  -1.750  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.414  -2.233  -1.283  1.00  0.00           H  
HETATM   30  H6  UNL     1      -5.441   0.368  -0.860  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.644   0.376   0.906  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.158  -1.156   0.142  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.928   2.921   1.743  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.424   2.231   1.277  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   22   22
CONECT    3    4    4    5
CONECT    5    6    6    7
CONECT    7    8   23   23
CONECT    8    9    9   24
CONECT    9   10   28
CONECT   10   11   29
CONECT   11   12   12   24
CONECT   12   13   14
CONECT   13   30   31   32
CONECT   14   15   15   16
CONECT   16   17   17   18
CONECT   18   19   24   24
CONECT   19   20   20   23
CONECT   20   21   33
CONECT   21   22   34
CONECT   22   23
END

HMDB0004068
     RDKit          3D
Melanin
 34 38  0  0  0  0  0  0  0  0999 V2000
    4.9930    0.0487   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5781   -0.3062   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1536   -1.4651   -0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0817   -2.1818   -1.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8227   -1.7807   -1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -2.7913   -1.7167 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009   -0.9193   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4591   -1.1204   -0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821   -2.0651   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837   -1.7022   -0.9792 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176   -0.5511   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.3047    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0042   -0.0396    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565    1.4434    0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0565    2.1850    1.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    1.7736    1.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250    2.7807    1.7048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    0.9150    0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4827    1.1221    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2868    2.0720    1.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888    1.7145    0.9815 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    0.5603    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220    0.1995    0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -0.2012   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1488    1.1436   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6095   -0.4643   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3219   -0.2590    0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -2.9229   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4138   -2.2332   -1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4407    0.3681   -0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6436    0.3763    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1575   -1.1561    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277    2.9214    1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240    2.2306    1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 24  2  0
 22  2  2  0
 23  7  2  0
 24  8  1  0
 24 11  1  0
 23 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  9 28  1  0
 10 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 20 33  1  0
 21 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Allomelanins	HMDB
Melanins	HMDB
Phaeomelanins	HMDB

Chemical Formula

C₁₈H₁₀N₂O₄

Average Molecular Weight

318.283

Monoisotopic Molecular Weight

318.064056818

IUPAC Name

6,14-dimethyl-4,12-diazapentacyclo[8.6.1.1²,⁵.0¹³,¹⁷.0⁹,¹⁸]octadeca-1(17),2,5,9(18),10,13-hexaene-7,8,15,16-tetrone

Traditional Name

melanin

CAS Registry Number

8049-97-6

SMILES

CC1=C2NC=C3C2=C(C2=CNC4=C(C)C(=O)C(=O)C3=C24)C(=O)C1=O

InChI Identifier

InChI=1S/C18H10N2O4/c1-5-13-9-7(3-19-13)12-10-8(11(9)17(23)15(5)21)4-20-14(10)6(2)16(22)18(12)24/h3-4,19-20H,1-2H3

InChI Key

XUMBMVFBXHLACL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
Indolequinone
Indole
Indole or derivatives
Isoindole
Isoindole or derivatives
Quinone
Vinylogous amide
Pyrrole
Heteroaromatic compound
Cyclic ketone
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Renal system and urinary system

Renal disorder

Chronic kidney disease (HMDB: HMDB0004068)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 10771134)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0004068)

Organ

Gland

Organ substructure

Adrenal medulla (HMDB: HMDB0004068)

Tissue

Epithelium

Epidermis (HMDB: HMDB0004068)

Connective tissue

Dermis (HMDB: HMDB0004068)

Tissue substructure

Hair (HMDB: HMDB0004068)

Cellular substructure

Cytoplasm (HMDB: HMDB0004068)
Myelin sheath (HMDB: HMDB0004068)

Source

Endogenous

Endogenous (HMDB: HMDB0004068)

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)
Tyrosine Metabolism (HMDB: HMDB0004068)

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 (HMDB: HMDB0004068)
Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Industrial application

Pharmaceutical industry

Biomarker

Chronic kidney disease (MarkerDB: MDB00000438)
Chronic Renal Failure (MarkerDB: MDB00000438)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	339700 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	1.76	ALOGPS
logP	-0.27	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.65	ChemAxon
pKa (Strongest Basic)	1.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.34 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.28 m³·mol⁻¹	ChemAxon
Polarizability	31.77 Å³	ChemAxon
Number of Rings	5	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]+	173.224	31661259
DarkChem	[M-H]-	171.228	31661259
DeepCCS	[M-2H]-	211.318	30932474
DeepCCS	[M+Na]+	186.643	30932474
AllCCS	[M+H]+	169.0	32859911
AllCCS	[M+H-H2O]+	165.5	32859911
AllCCS	[M+NH4]+	172.2	32859911
AllCCS	[M+Na]+	173.1	32859911
AllCCS	[M-H]-	177.0	32859911
AllCCS	[M+Na-2H]-	175.8	32859911
AllCCS	[M+HCOO]-	174.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melanin	CC1=C2NC=C3C2=C(C2=CNC4=C(C)C(=O)C(=O)C3=C24)C(=O)C1=O	3888.2	Standard polar	33892256
Melanin	CC1=C2NC=C3C2=C(C2=CNC4=C(C)C(=O)C(=O)C3=C24)C(=O)C1=O	3204.9	Standard non polar	33892256
Melanin	CC1=C2NC=C3C2=C(C2=CNC4=C(C)C(=O)C(=O)C3=C24)C(=O)C1=O	3981.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melanin,1TMS,isomer #1	CC1=C2[NH]C=C3C4=C5C(=CN([Si](C)(C)C)C5=C(C)C(=O)C4=O)C(=C23)C(=O)C1=O	3546.1	Semi standard non polar	33892256
Melanin,1TMS,isomer #1	CC1=C2[NH]C=C3C4=C5C(=CN([Si](C)(C)C)C5=C(C)C(=O)C4=O)C(=C23)C(=O)C1=O	3357.4	Standard non polar	33892256
Melanin,1TMS,isomer #1	CC1=C2[NH]C=C3C4=C5C(=CN([Si](C)(C)C)C5=C(C)C(=O)C4=O)C(=C23)C(=O)C1=O	4173.2	Standard polar	33892256
Melanin,2TMS,isomer #1	CC1=C2C3=C(C(=O)C1=O)C1=CN([Si](C)(C)C)C4=C(C)C(=O)C(=O)C(=C14)C3=CN2[Si](C)(C)C	3518.4	Semi standard non polar	33892256
Melanin,2TMS,isomer #1	CC1=C2C3=C(C(=O)C1=O)C1=CN([Si](C)(C)C)C4=C(C)C(=O)C(=O)C(=C14)C3=CN2[Si](C)(C)C	3383.8	Standard non polar	33892256
Melanin,2TMS,isomer #1	CC1=C2C3=C(C(=O)C1=O)C1=CN([Si](C)(C)C)C4=C(C)C(=O)C(=O)C(=C14)C3=CN2[Si](C)(C)C	3814.3	Standard polar	33892256
Melanin,1TBDMS,isomer #1	CC1=C2[NH]C=C3C4=C5C(=CN([Si](C)(C)C(C)(C)C)C5=C(C)C(=O)C4=O)C(=C23)C(=O)C1=O	3825.9	Semi standard non polar	33892256
Melanin,1TBDMS,isomer #1	CC1=C2[NH]C=C3C4=C5C(=CN([Si](C)(C)C(C)(C)C)C5=C(C)C(=O)C4=O)C(=C23)C(=O)C1=O	3524.9	Standard non polar	33892256
Melanin,1TBDMS,isomer #1	CC1=C2[NH]C=C3C4=C5C(=CN([Si](C)(C)C(C)(C)C)C5=C(C)C(=O)C4=O)C(=C23)C(=O)C1=O	4107.4	Standard polar	33892256
Melanin,2TBDMS,isomer #1	CC1=C2C3=C(C(=O)C1=O)C1=CN([Si](C)(C)C(C)(C)C)C4=C(C)C(=O)C(=O)C(=C14)C3=CN2[Si](C)(C)C(C)(C)C	4020.7	Semi standard non polar	33892256
Melanin,2TBDMS,isomer #1	CC1=C2C3=C(C(=O)C1=O)C1=CN([Si](C)(C)C(C)(C)C)C4=C(C)C(=O)C(=O)C(=C14)C3=CN2[Si](C)(C)C(C)(C)C	3754.9	Standard non polar	33892256
Melanin,2TBDMS,isomer #1	CC1=C2C3=C(C(=O)C1=O)C1=CN([Si](C)(C)C(C)(C)C)C4=C(C)C(=O)C(=O)C(=C14)C3=CN2[Si](C)(C)C(C)(C)C	3864.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Melanin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ku-0094000000-94704d5e412ed2489f17	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melanin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melanin 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 - Melanin 10V, Positive-QTOF	splash10-014i-0009000000-ca3bb49729033ec75f80	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 20V, Positive-QTOF	splash10-014l-0089000000-bc7ad58775b231f90e84	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 40V, Positive-QTOF	splash10-0229-0090000000-dc286795a5fc4078c357	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 10V, Negative-QTOF	splash10-014i-0009000000-80dff8e14771680560aa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 20V, Negative-QTOF	splash10-014i-0019000000-395c4a7d06b442e4dcf1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 40V, Negative-QTOF	splash10-06ri-0091000000-760c7a558bb6db841316	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 10V, Negative-QTOF	splash10-014i-0009000000-4e47ddd4efc907375a4f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 20V, Negative-QTOF	splash10-014i-0009000000-2c08c7c7a9e445b436e4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 40V, Negative-QTOF	splash10-07ci-0091000000-438444e04c7ab334b33a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 10V, Positive-QTOF	splash10-014i-0009000000-92cfd0e072e19008dfb4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 20V, Positive-QTOF	splash10-014i-0009000000-92cfd0e072e19008dfb4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melanin 40V, Positive-QTOF	splash10-03di-0092000000-a9de3724b70ffcb23cf8	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood

Tissue Locations

Adrenal Gland
Adrenal Medulla
Bladder
Epidermis
Fibroblasts
Hair
Neuron
Spleen
Thyroid Gland

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
Blood	Detected and Quantified	5345 +/- 318 uM	Adult (>18 years old)	Both	Normal	2474282	details
Blood	Detected and Quantified	5030.0 +/- 314.0 uM	Adult (>18 years old)	Both	Normal	10771134	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	8551 +/- 1194 uM	Adult (>18 years old)	Both	Chronic renal failure	2474282	details

Associated Disorders and Diseases

Disease References

Chronic renal failure
Hegedus ZL, Frank HA, Steinman TI, Altschule MD, Nayak U: Elevated levels of plasma lipofuscins in patients with chronic renal failure. Arch Int Physiol Biochim. 1988 Dec;96(5):211-21. [PubMed:2474282 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023298

KNApSAcK ID

Not Available

Chemspider ID

4884931

KEGG Compound ID

C05606

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

89634

Food Biomarker Ontology

Not Available

VMH ID

MELANIN

MarkerDB ID

MDB00000438

Good Scents ID

rw1359121

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Pugh ND, Balachandran P, Lata H, Dayan FE, Joshi V, Bedir E, Makino T, Moraes R, Khan I, Pasco DS: Melanin: dietary mucosal immune modulator from Echinacea and other botanical supplements. Int Immunopharmacol. 2005 Apr;5(4):637-47. [PubMed:15710333 ]
Borges CR, Roberts JC, Wilkins DG, Rollins DE: Relationship of melanin degradation products to actual melanin content: application to human hair. Anal Biochem. 2001 Mar 1;290(1):116-25. [PubMed:11180945 ]
Alaluf S, Atkins D, Barrett K, Blount M, Carter N, Heath A: The impact of epidermal melanin on objective measurements of human skin colour. Pigment Cell Res. 2002 Apr;15(2):119-26. [PubMed:11936269 ]
Wenczl E, Van der Schans GP, Roza L, Kolb RM, Timmerman AJ, Smit NP, Pavel S, Schothorst AA: (Pheo)melanin photosensitizes UVA-induced DNA damage in cultured human melanocytes. J Invest Dermatol. 1998 Oct;111(4):678-82. [PubMed:9764853 ]
Nielsen KP, Zhao L, Stamnes JJ, Stamnes K, Moan J: The importance of the depth distribution of melanin in skin for DNA protection and other photobiological processes. J Photochem Photobiol B. 2006 Mar 1;82(3):194-8. Epub 2006 Jan 4. [PubMed:16388960 ]
Watanabe T, Tamura A, Yoshimura Y, Nakazawa H: Determination of melanin in human hair by photoacoustic spectroscopy. Anal Biochem. 1997 Dec 15;254(2):267-71. [PubMed:9417788 ]
Claridge E, Cotton S, Hall P, Moncrieff M: From colour to tissue histology: Physics-based interpretation of images of pigmented skin lesions. Med Image Anal. 2003 Dec;7(4):489-502. [PubMed:14561553 ]
Schmidt R, Krien P, Regnier M: The use of diethylaminoethyl-cellulose-membrane filters in a bioassay to quantify melanin synthesis. Anal Biochem. 1996 Mar 15;235(2):113-8. [PubMed:8833318 ]
Lu H, Edwards C, Gaskell S, Pearse A, Marks R: Melanin content and distribution in the surface corneocyte with skin phototypes. Br J Dermatol. 1996 Aug;135(2):263-7. [PubMed:8881670 ]
Kronstrand R, Forstberg-Peterson S, Kagedal B, Ahlner J, Larson G: Codeine concentration in hair after oral administration is dependent on melanin content. Clin Chem. 1999 Sep;45(9):1485-94. [PubMed:10471651 ]
Bartosik J, Wulf HC, Kobayasi T: Melanin and melanosome complexes in long standing stable vitiligo--an ultrastructural study. Eur J Dermatol. 1998 Mar;8(2):95-7. [PubMed:9649719 ]
Svensson SP, Lindgren S, Powell W, Green H: Melanin inhibits cytotoxic effects of doxorubicin and daunorubicin in MOLT 4 cells. Pigment Cell Res. 2003 Aug;16(4):351-4. [PubMed:12859618 ]
Dwyer T, Muller HK, Blizzard L, Ashbolt R, Phillips G: The use of spectrophotometry to estimate melanin density in Caucasians. Cancer Epidemiol Biomarkers Prev. 1998 Mar;7(3):203-6. [PubMed:9521433 ]
Shimada M, Yamada Y, Itoh M, Yatagai T: Melanin and blood concentration in human skin studied by multiple regression analysis: experiments. Phys Med Biol. 2001 Sep;46(9):2385-95. [PubMed:11580175 ]
Yamashita T, Kuwahara T, Gonzalez S, Takahashi M: Non-invasive visualization of melanin and melanocytes by reflectance-mode confocal microscopy. J Invest Dermatol. 2005 Jan;124(1):235-40. [PubMed:15654979 ]
Huang Z, Zeng H, Hamzavi I, Alajlan A, Tan E, McLean DI, Lui H: Cutaneous melanin exhibiting fluorescence emission under near-infrared light excitation. J Biomed Opt. 2006 May-Jun;11(3):34010. [PubMed:16822060 ]
Eng HL, Chen WJ: Melanin-producing medullary carcinoma of the thyroid gland. Arch Pathol Lab Med. 1989 Apr;113(4):377-80. [PubMed:2705868 ]
Mammone T, Marenus K, Muizzuddin N, Maes D: Evidence and utility of melanin degrading enzymes. J Cosmet Sci. 2004 Jan-Feb;55(1):116-7. [PubMed:15037924 ]
Shimada M, Yamada Y, Itoh M, Yatagai T: Melanin and blood concentration in a human skin model studied by multiple regression analysis: assessment by Monte Carlo simulation. Phys Med Biol. 2001 Sep;46(9):2397-406. [PubMed:11580176 ]
Nishidate I, Aizu Y, Mishina H: Depth visualization of a local blood region in skin tissue by use of diffuse reflectance images. Opt Lett. 2005 Aug 15;30(16):2128-30. [PubMed:16127932 ]

Enzymes

Enzyme Details

1. 5,6-dihydroxyindole-2-carboxylic acid oxidase

General function:: Involved in copper ion binding
Specific function:: Oxidation of 5,6-dihydroxyindole-2-carboxylic acid (DHICA) into indole-5,6-quinone-2-carboxylic acid. May regulate or influence the type of melanin synthesized
Gene Name:: TYRP1
Uniprot ID:: P17643
Molecular weight:: 60723.8

Enzyme Details

2. P protein

General function:: Involved in arsenite transmembrane transporter activity
Specific function:: Could be involved in the transport of tyrosine, the precursor to melanin synthesis, within the melanocyte. Regulates the pH of melanosome and the melanosome maturation. One of the components of the mammalian pigmentary system. Seems to regulate the post-translational processing of tyrosinase, which catalyzes the limiting reaction in melanin synthesis. May serve as a key control point at which ethnic skin color variation is determined. Major determinant of brown and/or blue eye color
Gene Name:: OCA2
Uniprot ID:: Q04671
Molecular weight:: 92848.5

Showing metabocard for Melanin (HMDB0004068)

MOL for HMDB0004068 (Melanin)

3D MOL for HMDB0004068 (Melanin)

3D SDF for HMDB0004068 (Melanin)

3D-SDF for HMDB0004068 (Melanin)

PDB for HMDB0004068 (Melanin)

3D PDB for HMDB0004068 (Melanin)

SMILES for HMDB0004068 (Melanin)

INCHI for HMDB0004068 (Melanin)

Structure for HMDB0004068 (Melanin)

3D Structure for HMDB0004068 (Melanin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes