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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-07 16:45:29 UTC

HMDB ID

HMDB0001389

Secondary Accession Numbers

HMDB01389

Metabolite Identification

Common Name

Melatonin

Description

Melatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B. Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and. lowering the body temperature. Melatonin is also implicated in the regulation of mood,learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders(ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits. were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers.

Structure

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

HMDB0001389
     RDKit          3D
Melatonin
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.5190    0.8642    0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660    1.1027    0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389    0.2276    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2909   -1.1396    0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246   -1.9959    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -1.5480    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2528   -2.1439    0.4042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1846   -1.1815    0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0308    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1759    1.4172   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680    1.4338    0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4487    0.7155    0.0944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3954    0.0223   -0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854   -0.2384   -2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4612   -0.5000   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -0.1939    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8512    0.6358    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0462    1.8624    0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055    0.3933    1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0142    0.3383   -0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3092   -1.4419    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468   -3.0491    0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4781   -3.1588    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -1.4415   -0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912    2.1497    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    1.6268   -1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0873    0.9815    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6752    2.4920    0.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2565    0.8334    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7888   -0.0298   -2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1205    0.5149   -2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -1.2739   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492    1.6938    0.1189 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  9 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
M  END

  Mrv1652302032018022D          

 17 18  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.0468 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.7613 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1185 9997.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3115 9997.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.046710000.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001389

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC=C2CCNC(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)

> <INCHI_KEY>
DRLFMBDRBRZALE-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O2

> <MOLECULAR_WEIGHT>
232.2783

> <EXACT_MASS>
232.121177766

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.649878848425523

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.1476127873333333

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.59127620174317

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.795496949109147

> <JCHEM_PKA_STRONGEST_BASIC>
-1.568617764839225

> <JCHEM_POLAR_SURFACE_AREA>
54.120000000000005

> <JCHEM_REFRACTIVITY>
66.2799

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melatonin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001389
     RDKit          3D
Melatonin
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.5190    0.8642    0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660    1.1027    0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389    0.2276    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2909   -1.1396    0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246   -1.9959    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -1.5480    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2528   -2.1439    0.4042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1846   -1.1815    0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0308    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1759    1.4172   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680    1.4338    0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4487    0.7155    0.0944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3954    0.0223   -0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854   -0.2384   -2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4612   -0.5000   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -0.1939    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8512    0.6358    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0462    1.8624    0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055    0.3933    1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0142    0.3383   -0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3092   -1.4419    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468   -3.0491    0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4781   -3.1588    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -1.4415   -0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912    2.1497    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    1.6268   -1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0873    0.9815    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6752    2.4920    0.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2565    0.8334    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7888   -0.0298   -2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1205    0.5149   -2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -1.2739   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492    1.6938    0.1189 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  9 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 03-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-FEB-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8669.1548664.625   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8670.4878665.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8671.8218664.625   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8661.2888661.519   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8659.7818661.199   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8670.4878666.935   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   14   17   12                                                  
CONECT   14   13                                                            
CONECT   15    3   16                                                       
CONECT   16   15                                                            
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0001389
HETATM    1  C1  UNL     1       5.519   0.864   0.781  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.166   1.103   0.558  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.139   0.228   0.552  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.291  -1.140   0.792  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.225  -1.996   0.772  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.935  -1.548   0.514  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.253  -2.144   0.404  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.185  -1.182   0.098  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.604   0.031   0.014  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.176   1.417  -0.135  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.468   1.434   0.738  1.00  0.00           C  
HETATM   12  N2  UNL     1      -3.449   0.716   0.094  1.00  0.00           N  
HETATM   13  C10 UNL     1      -4.395   0.022  -0.527  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.885  -0.238  -2.086  1.00  0.00           C  
HETATM   15  O2  UNL     1      -5.461  -0.500  -0.484  1.00  0.00           O  
HETATM   16  C12 UNL     1       0.758  -0.194   0.276  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.851   0.636   0.303  1.00  0.00           C  
HETATM   18  H1  UNL     1       6.046   1.862   0.828  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.706   0.393   1.763  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.014   0.338  -0.064  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.309  -1.442   0.995  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.347  -3.049   0.958  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.478  -3.159   0.539  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.215  -1.442  -0.030  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.491   2.150   0.264  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.394   1.627  -1.168  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.087   0.982   1.710  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.675   2.492   0.919  1.00  0.00           H  
HETATM   29  H12 UNL     1      -4.256   0.833   1.188  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.789  -0.030  -2.645  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.120   0.515  -2.170  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.573  -1.274  -1.972  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.649   1.694   0.119  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   16
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   16
CONECT   10   11   25   26
CONECT   11   12   27   28
CONECT   12   13   29
CONECT   13   14   15   15
CONECT   14   30   31   32
CONECT   16   17   17
CONECT   17   33
END

HMDB0001389
     RDKit          3D
Melatonin
 33 34  0  0  0  0  0  0  0  0999 V2000
    5.5190    0.8642    0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660    1.1027    0.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389    0.2276    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2909   -1.1396    0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246   -1.9959    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -1.5480    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2528   -2.1439    0.4042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1846   -1.1815    0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0308    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1759    1.4172   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680    1.4338    0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4487    0.7155    0.0944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3954    0.0223   -0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854   -0.2384   -2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4612   -0.5000   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -0.1939    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8512    0.6358    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0462    1.8624    0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055    0.3933    1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0142    0.3383   -0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3092   -1.4419    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468   -3.0491    0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4781   -3.1588    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2151   -1.4415   -0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912    2.1497    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    1.6268   -1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0873    0.9815    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6752    2.4920    0.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2565    0.8334    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7888   -0.0298   -2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1205    0.5149   -2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -1.2739   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492    1.6938    0.1189 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  9 16  1  0
 16 17  2  0
 17  3  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Methoxy-N-acetyltryptamine	ChEBI
Melatonine	ChEBI
N-[2-(5-Methoxyindol-3-yl)ethyl]acetamide	ChEBI
N-Acetyl-5-methoxytryptamine	ChEBI
Melatonina	Kegg
Circadin	HMDB
Melatol	HMDB
Melatonin (synth.) standard-grade	HMDB
Melatonin (synth.) ultra-pure	HMDB
Melovine	HMDB
MT6	HMDB
N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide	HMDB
N-(2-(5-Methoxyindol-3-yl)ethyl)-acetamide	HMDB
N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide	HMDB
N-Acetyl-5-methoxy-tryptamine	HMDB
N-Acetyl-5-methoxy-tryptamine melatonine	HMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide	HMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-acetamide	HMDB
N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide	HMDB
N-[2-(5-Methoxyindol-3-yl)ethyl]-acetamide	HMDB
Regulin	HMDB
{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} acetamide	HMDB
{N-[2-(5-methoxyindol-3-yl)ethyl]-} acetamide	HMDB
3-(2-Acetamidoethyl)-5-methoxyindole	HMDB
Melatonin	HMDB

Chemical Formula

C₁₃H₁₆N₂O₂

Average Molecular Weight

232.2783

Monoisotopic Molecular Weight

232.121177766

IUPAC Name

N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide

Traditional Name

melatonin

CAS Registry Number

73-31-4

SMILES

COC1=CC2=C(NC=C2CCNC(C)=O)C=C1

InChI Identifier

InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)

InChI Key

DRLFMBDRBRZALE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Anisole
Alkyl aryl ether
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Propargyl-type 1,3-dipolar organic compound
Ether
Carboximidic acid derivative
Carboximidic acid
Organic 1,3-dipolar compound
Azacycle
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acetamides (CHEBI:16796 )
tryptamines (CHEBI:16796 )
Indole alkaloids (C01598 )
Melatonin (C01598 )
a small molecule (N-ACETYL-5-METHOXY-TRYPTAMINE )

Ontology

Physiological effect

Health effect

Cancer

Cancer (HMDB: HMDB0001389)

Renal system and urinary system

Renal disorder

Uremia (HMDB: HMDB0001389)

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Psychological development disorder

Autism (HMDB: HMDB0001389)
Autism spectrum disorder (HMDB: HMDB0001389)

Observation

Drowsiness (HMDB: HMDB0001389)

Adipose tissue (HMDB: HMDB0001389)
Adipose tissue (HMDB: HMDB0001389)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12675874)
Cerebrospinal Fluid (CSF) (PMID: 10960829)
Saliva (HMDB: HMDB0001389)
Cerebrospinal fluid (HMDB: HMDB0001389)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0001389)

Hematocyte

Platelet (HMDB: HMDB0001389)
Neutrophil (HMDB: HMDB0001389)

Urine (PMID: 28916042)

Cellular substructure

Cytoplasm (HMDB: HMDB0001389)
Extracellular (HMDB: HMDB0001389)

Gastrointestinal Tract (HMDB: HMDB0001389)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001389)

Source

Exogenous

Exogenous (HMDB: HMDB0001389)

Food

Food (HMDB: HMDB0001389)

Animal origin

Poultry

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)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Coffee and coffee product

Coffee

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Baking good

Condiment

Mustard (FooDB: FOOD00654)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Beverage

Fermented beverage

Red wine (FooDB: FOOD00911)

Endogenous

Endogenous (HMDB: HMDB0001389)

Plant

Animal

Animal (HMDB: HMDB0001389)

Microbe

Microbe (HMDB: HMDB0001389)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (HMDB: HMDB0001389)
Tryptophan Metabolism (HMDB: HMDB0001389)

System process

Reproduction (HMDB: HMDB0001389)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001389)
Contraceptive (HMDB: HMDB0001389)

Biomarker

Uremia (MarkerDB: MDB00000319)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0001389)
Immunological adjuvant (HMDB: HMDB0001389)
Anticonvulsant (HMDB: HMDB0001389)

Solid material processing agent

Protective agent

Central nervous system depressant (HMDB: HMDB0001389)
GABA agent (HMDB: HMDB0001389)

Biological role

Human metabolite (HMDB: HMDB0001389)
Free radical scavenger (HMDB: HMDB0001389)
Anaphrodisiac (HMDB: HMDB0001389)
Anti aggregant (HMDB: HMDB0001389)
Anti convulsant (HMDB: HMDB0001389)
Anti depressant (HMDB: HMDB0001389)
Anti gonadotrophic (HMDB: HMDB0001389)
Anti insomniac (HMDB: HMDB0001389)
Anti radicular (HMDB: HMDB0001389)
Anti thyreotropic (HMDB: HMDB0001389)
Aphrodisiac (HMDB: HMDB0001389)
Depressant (HMDB: HMDB0001389)
GABAnergic (HMDB: HMDB0001389)
Gonadotrophic (HMDB: HMDB0001389)
Hypnotic (HMDB: HMDB0001389)
Hypocholesterolemic (HMDB: HMDB0001389)
Hypothermic (HMDB: HMDB0001389)
Progesteronigenic (HMDB: HMDB0001389)
Serotoninergic (HMDB: HMDB0001389)
Thyrotropic (HMDB: HMDB0001389)

Molecular messenger

Hormone (HMDB: HMDB0001389)
Hormone (HMDB: HMDB0001389)

Modulator

Immunomodulator (HMDB: HMDB0001389)

Inhibitor

Cyclooxygenase 2 inhibitor (HMDB: HMDB0001389)
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (HMDB: HMDB0001389)

Enzyme inhibitor

Cyclooxygenase inhibitor (HMDB: HMDB0001389)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	117 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	153.534	30932474
[M+H]+	CBM	153.4	30932474
[M+H]+	MetCCS_train_pos	154.331	30932474
[M-H]-	Not Available	155.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000337
[M+H]+	Not Available	154.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000337

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.15	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.8	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.28 m³·mol⁻¹	ChemAxon
Polarizability	25.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.92	31661259
DarkChem	[M-H]-	154.287	31661259
AllCCS	[M+H]+	153.249	32859911
AllCCS	[M-H]-	157.775	32859911
DeepCCS	[M+H]+	154.283	30932474
DeepCCS	[M-H]-	151.925	30932474
DeepCCS	[M-2H]-	184.933	30932474
DeepCCS	[M+Na]+	160.376	30932474
AllCCS	[M+H]+	153.2	32859911
AllCCS	[M+H-H2O]+	149.4	32859911
AllCCS	[M+NH4]+	156.8	32859911
AllCCS	[M+Na]+	157.9	32859911
AllCCS	[M-H]-	157.8	32859911
AllCCS	[M+Na-2H]-	157.9	32859911
AllCCS	[M+HCOO]-	158.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melatonin	COC1=CC2=C(NC=C2CCNC(C)=O)C=C1	3493.8	Standard polar	33892256
Melatonin	COC1=CC2=C(NC=C2CCNC(C)=O)C=C1	2388.8	Standard non polar	33892256
Melatonin	COC1=CC2=C(NC=C2CCNC(C)=O)C=C1	2436.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melatonin,1TMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C	2455.1	Semi standard non polar	33892256
Melatonin,1TMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C	2391.9	Standard non polar	33892256
Melatonin,1TMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C	2942.9	Standard polar	33892256
Melatonin,1TMS,isomer #2	COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1	2337.0	Semi standard non polar	33892256
Melatonin,1TMS,isomer #2	COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1	2493.9	Standard non polar	33892256
Melatonin,1TMS,isomer #2	COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C)C2=C1	2961.8	Standard polar	33892256
Melatonin,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C	2377.2	Semi standard non polar	33892256
Melatonin,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C	2552.5	Standard non polar	33892256
Melatonin,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C)=CN2[Si](C)(C)C	2692.7	Standard polar	33892256
Melatonin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C	2675.3	Semi standard non polar	33892256
Melatonin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C	2586.8	Standard non polar	33892256
Melatonin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)=CN2[Si](C)(C)C(C)(C)C	2999.0	Standard polar	33892256
Melatonin,1TBDMS,isomer #2	COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1	2585.8	Semi standard non polar	33892256
Melatonin,1TBDMS,isomer #2	COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1	2690.6	Standard non polar	33892256
Melatonin,1TBDMS,isomer #2	COC1=CC=C2[NH]C=C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1	3015.2	Standard polar	33892256
Melatonin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2803.8	Semi standard non polar	33892256
Melatonin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2933.3	Standard non polar	33892256
Melatonin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2857.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Melatonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001i-0490000000-aa93967315af900a76ce	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Melatonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-03k9-0900000000-a15ee6def3f8d75b1231	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Melatonin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001j-0490000000-94ef1be9ab930060778a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Melatonin GC-MS (2 TMS)	splash10-001i-1490000000-03e24298c7bd1ed4066a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Melatonin GC-MS (Non-derivatized)	splash10-001i-1490000000-03e24298c7bd1ed4066a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Melatonin GC-EI-TOF (Non-derivatized)	splash10-001j-0590000000-63d5e32dd5f7877a4402	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Melatonin GC-EI-TOF (Non-derivatized)	splash10-001i-0590000000-52b3a733f8b49582d3fb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Melatonin GC-EI-TOF (Non-derivatized)	splash10-0229-1900000000-d81c6f617bc486066136	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melatonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-4920000000-a8d9d614e9f8769a1359	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melatonin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melatonin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03k9-1900000000-45ee4fdc7acdb33dad3b	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-0920000000-f90ec9b77e1a245e35a8	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-05fr-0900000000-49e4482c65e82ac64b66	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-003r-0900000000-8a4ae0fd610cca992d74	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0159-0090000000-939a1caf5760c0ba189c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0006-0930000000-9e6fcea2c634ac9d85a0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0006-0900000000-ddd29e731a7de56c1808	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0006-0900000000-34b4fb52810a15ea5bd6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-001i-0090000000-5ca2df63ec2baefdae8c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-001i-0190000000-5bae6e63e9b40e60e0a4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-00di-0900000000-529bf6d5c2091993f865	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-00di-0900000000-158a60fe696120b23b41	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-0a5c-0900000000-5e86b2de659ce47762c0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-001i-0900000000-881c0d57239d56c46f2d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-00di-0910000000-f256f78adbcbeb2464de	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0a4i-0900000000-bd15d952a2fc6c5cbb23	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin DI-ESI-qTof , Positive-QTOF	splash10-05fr-0900000000-7acf9405f4beeb34566c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin DI-ESI-qTof , Positive-QTOF	splash10-00di-0900000000-13245183cd8c8cd511c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-qTof , Positive-QTOF	splash10-05ai-2900000000-07b3d32f002dba733c10	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Melatonin LC-ESI-QQ , negative-QTOF	splash10-0159-0090000000-939a1caf5760c0ba189c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin 10V, Positive-QTOF	splash10-0019-0950000000-3561167f9cf6abf87465	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin 20V, Positive-QTOF	splash10-00dr-0900000000-7c590c12649f6abfac96	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin 40V, Positive-QTOF	splash10-006x-1900000000-6fc07c212072dc15cda1	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin 10V, Negative-QTOF	splash10-001i-1390000000-afe87f80bc60da102bf6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin 20V, Negative-QTOF	splash10-0019-3940000000-44812f1a2c7f6216bd23	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin 40V, Negative-QTOF	splash10-052f-9300000000-995e110e7943eff538ad	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Saliva
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Brain
Fibroblasts
Intestine
Kidney
Leukocyte
Liver
Neuron
Ovary
Pancreas
Pineal Gland
Placenta
Platelet
Prostate
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.00019 +/- 0.00015 uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.00006 +/- 0.000015 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.000063 +/- 0.000026 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.00256 +/- 0.00168 uM	Infant (0-1 year old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.000210 +/- 5.635e-05 uM	Adult (>18 years old)	Both	Normal	12675874	details
Blood	Detected and Quantified	0.00006 +/- 0.000015 uM	Newborn (0-30 days old)	Male	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0279 (0.00-0.0558) uM	Adult (>18 years old)	Both	Normal	10960829	details
Saliva	Detected and Quantified	0.191 +/- 0.201 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	0.0000033 (0.0000006-0.000006) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00140 +/- 0.00103 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Urine	Detected and Quantified	0.00210 umol/mmol creatinine	Adult (>18 years old)	Female	Pregnancy	28916042	details

Associated Disorders and Diseases

Disease References

Uremia

Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]

Associated OMIM IDs

None

External Links

DrugBank ID

DB01065

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004234

KNApSAcK ID

Not Available

Chemspider ID

872

KEGG Compound ID

C01598

BioCyc ID

N-ACETYL-5-METHOXY-TRYPTAMINE

BiGG ID

37965

Wikipedia Link

Melatonin

METLIN ID

PubChem Compound

896

PDB ID

Not Available

ChEBI ID

16796

Food Biomarker Ontology

Not Available

VMH ID

MELATN

MarkerDB ID

MDB00000319

Good Scents ID

Not Available

References

Synthesis Reference

Helmut M. Hügel and Faizul Nurlawis. Short synthesis of melatonin. Heterocycles (2003), Vol. 60, No. 10, pp. 2349 - 2354.

Material Safety Data Sheet (MSDS)

Not Available

General References

Slominski A, Pisarchik A, Zbytek B, Tobin DJ, Kauser S, Wortsman J: Functional activity of serotoninergic and melatoninergic systems expressed in the skin. J Cell Physiol. 2003 Jul;196(1):144-53. [PubMed:12767050 ]
Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [PubMed:15992934 ]
Christofides J, Bridel M, Egerton M, Mackay GM, Forrest CM, Stoy N, Darlington LG, Stone TW: Blood 5-hydroxytryptamine, 5-hydroxyindoleacetic acid and melatonin levels in patients with either Huntington's disease or chronic brain injury. J Neurochem. 2006 May;97(4):1078-88. Epub 2006 Mar 29. [PubMed:16573644 ]
Drake MJ, Mills IW, Noble JG: Melatonin pharmacotherapy for nocturia in men with benign prostatic enlargement. J Urol. 2004 Mar;171(3):1199-202. [PubMed:14767300 ]
Lahiri DK, Chen D, Lahiri P, Rogers JT, Greig NH, Bondy S: Melatonin, metals, and gene expression: implications in aging and neurodegenerative disorders. Ann N Y Acad Sci. 2004 Dec;1035:216-30. [PubMed:15681810 ]
Bangha E, Lauth D, Kistler GS, Elsner P: Daytime serum levels of melatonin after topical application onto the human skin. Skin Pharmacol. 1997;10(5-6):298-302. [PubMed:9449169 ]
Bubenik GA: Localization, physiological significance and possible clinical implication of gastrointestinal melatonin. Biol Signals Recept. 2001 Nov-Dec;10(6):350-66. [PubMed:11721091 ]
Abdel-Wahhab MA, Abdel-Galil MM, El-Lithey M: Melatonin counteracts oxidative stress in rats fed an ochratoxin A contaminated diet. J Pineal Res. 2005 Mar;38(2):130-5. [PubMed:15683468 ]
Chen HM, Hsu JT, Chen JC, Ng CJ, Chiu DF, Chen MF: Delayed neutrophil apoptosis attenuated by melatonin in human acute pancreatitis. Pancreas. 2005 Nov;31(4):360-4. [PubMed:16258371 ]
Fabis M, Pruszynska E, Mackowiak P: In vivo and in situ action of melatonin on insulin secretion and some metabolic implications in the rat. Pancreas. 2002 Aug;25(2):166-9. [PubMed:12142740 ]
Messner M, Huether G, Lorf T, Ramadori G, Schworer H: Presence of melatonin in the human hepatobiliary-gastrointestinal tract. Life Sci. 2001 Jun 22;69(5):543-51. [PubMed:11510949 ]
Nishida S: Metabolic effects of melatonin on oxidative stress and diabetes mellitus. Endocrine. 2005 Jul;27(2):131-6. [PubMed:16217126 ]
Peschke E, Frese T, Chankiewitz E, Peschke D, Preiss U, Schneyer U, Spessert R, Muhlbauer E: Diabetic Goto Kakizaki rats as well as type 2 diabetic patients show a decreased diurnal serum melatonin level and an increased pancreatic melatonin-receptor status. J Pineal Res. 2006 Mar;40(2):135-43. [PubMed:16441550 ]
Reiter RJ, Sainz RM, Lopez-Burillo S, Mayo JC, Manchester LC, Tan DX: Melatonin ameliorates neurologic damage and neurophysiologic deficits in experimental models of stroke. Ann N Y Acad Sci. 2003 May;993:35-47; discussion 48-53. [PubMed:12853293 ]
Okatani Y, Wakatsuki A, Shinohara K, Kaneda C, Fukaya T: Melatonin stimulates glutathione peroxidase activity in human chorion. J Pineal Res. 2001 May;30(4):199-205. [PubMed:11339508 ]
Bubenik GA: Gastrointestinal melatonin: localization, function, and clinical relevance. Dig Dis Sci. 2002 Oct;47(10):2336-48. [PubMed:12395907 ]
Wurtman RJ, Ozaki Y: Physiological control of melatonin synthesis and secretion: mechanisms, generating rhythms in melatonin, methoxytryptophol, and arginine vasotocin levels and effects on the pineal of endogenous catecholamines, the estrous cycle, and environmental lighting. J Neural Transm Suppl. 1978;(13):59-70. [PubMed:288858 ]
Kobayashi H, Kromminga A, Dunlop TW, Tychsen B, Conrad F, Suzuki N, Memezawa A, Bettermann A, Aiba S, Carlberg C, Paus R: A role of melatonin in neuroectodermal-mesodermal interactions: the hair follicle synthesizes melatonin and expresses functional melatonin receptors. FASEB J. 2005 Oct;19(12):1710-2. Epub 2005 Jul 19. [PubMed:16030176 ]
Johe PD, Osterud B: The in vivo effect of melatonin on cellular activation processes in human blood during strenuous physical exercise. J Pineal Res. 2005 Oct;39(3):324-30. [PubMed:16150115 ]
Paakkonen T, Makinen TM, Leppaluoto J, Vakkuri O, Rintamaki H, Palinkas LA, Hassi J: Urinary melatonin: a noninvasive method to follow human pineal function as studied in three experimental conditions. J Pineal Res. 2006 Mar;40(2):110-5. [PubMed:16441547 ]
Atkinson G, Holder A, Robertson C, Gant N, Drust B, Reilly T, Waterhouse J: Effects of melatonin on the thermoregulatory responses to intermittent exercise. J Pineal Res. 2005 Nov;39(4):353-9. [PubMed:16207290 ]
Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. [PubMed:7773197 ]
Reiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. [PubMed:11462772 ]
Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. [PubMed:15206778 ]
Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. [PubMed:16217125 ]
Ma X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. doi: 10.1210/en.2007-1412. Epub 2008 Jan 10. [PubMed:18187545 ]

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Acetylserotonin O-methyltransferase

General function:: Involved in O-methyltransferase activity
Specific function:: Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name:: ASMT
Uniprot ID:: P46597
Molecular weight:: 41660.34

Reactions

S-Adenosylmethionine + N-Acetylserotonin → S-Adenosylhomocysteine + Melatonin	details

References

Minneman KP, Wurtman RJ: The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51. [PubMed:180879 ]

Enzyme Details

2. Ribosyldihydronicotinamide dehydrogenase [quinone]

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO2
Uniprot ID:: P16083
Molecular weight:: 25918.4

References

Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. [PubMed:19463840 ]

Enzyme Details

3. Myeloperoxidase

General function:: Involved in peroxidase activity
Specific function:: Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:: MPO
Uniprot ID:: P05164
Molecular weight:: 83867.71

References

Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. [PubMed:15636586 ]
Galijasevic S, Abdulhamid I, Abu-Soud HM: Melatonin is a potent inhibitor for myeloperoxidase. Biochemistry. 2008 Feb 26;47(8):2668-77. doi: 10.1021/bi702016q. Epub 2008 Feb 1. [PubMed:18237195 ]

Enzyme Details

4. Eosinophil peroxidase

General function:: Involved in peroxidase activity
Specific function:: Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis.
Gene Name:: EPX
Uniprot ID:: P11678
Molecular weight:: 81039.5

References

Lu T, Galijasevic S, Abdulhamid I, Abu-Soud HM: Analysis of the mechanism by which melatonin inhibits human eosinophil peroxidase. Br J Pharmacol. 2008 Jul;154(6):1308-17. doi: 10.1038/bjp.2008.173. Epub 2008 Jun 2. [PubMed:18516076 ]

Enzyme Details

5. Indoleamine 2,3-dioxygenase 1

General function:: Involved in heme binding
Specific function:: Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:: IDO1
Uniprot ID:: P14902
Molecular weight:: 45325.89

Reactions

Melatonin + Oxygen → Acetyl-N-formyl-5-methoxykynurenamine	details

References

Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. [PubMed:15636586 ]

Enzyme Details

6. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [PubMed:20167001 ]

Enzyme Details

7. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Huuhka K, Riutta A, Haataja R, Ylitalo P, Leinonen E: The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: A randomized, double-blind, placebo-controlled study. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):447-50. [PubMed:17003850 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Cytochrome P450 1B1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

References

Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [PubMed:19919601 ]
Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [PubMed:15616152 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

9. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [PubMed:19919601 ]
Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [PubMed:15616152 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

10. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [PubMed:19919601 ]
Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [PubMed:15616152 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. [PubMed:15626586 ]

Only showing the first 10 proteins. There are 18 proteins in total.

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Showing metabocard for Melatonin (HMDB0001389)

MOL for HMDB0001389 (Melatonin)

3D MOL for HMDB0001389 (Melatonin)

3D SDF for HMDB0001389 (Melatonin)

3D-SDF for HMDB0001389 (Melatonin)

PDB for HMDB0001389 (Melatonin)

3D PDB for HMDB0001389 (Melatonin)

SMILES for HMDB0001389 (Melatonin)

INCHI for HMDB0001389 (Melatonin)

Structure for HMDB0001389 (Melatonin)

3D Structure for HMDB0001389 (Melatonin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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