MiMeDB: Showing metabocard for Melatonin (MMDBc0048361)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:58:07 UTC

Update Date

2024-09-27 20:22:30 UTC

Metabolite ID

MMDBc0048361

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>
MMDBc0048361

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₃H₁₆N₂O₂

Average Mass

232.2783

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Blood
Brain
Cerebrospinal Fluid (CSF)
Feces
Fibroblasts
Intestine
Kidney
Leukocyte
Liver
Neuron
Ovary
Pancreas
Pineal Gland
Placenta
Platelet
Prostate
Saliva
Testis
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

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191774	Acetylserotonin O-methyltransferase	Unknown	P46597	Homo sapiens
MMDBp0191809	Ribosyldihydronicotinamide dehydrogenase [quinone]	Unknown	P16083	Homo sapiens
MMDBp0191952	Myeloperoxidase	Unknown	P05164	Homo sapiens
MMDBp0191955	Eosinophil peroxidase	Unknown	P11678	Homo sapiens
MMDBp0192103	Indoleamine 2,3-dioxygenase 1	Unknown	P14902	Homo sapiens
MMDBp0192647	Cytochrome P450 2C9	Unknown	P11712	Homo sapiens
MMDBp0192649	Cytochrome P450 2C19	Unknown	P33261	Homo sapiens
MMDBp0193102	Cytochrome P450 1B1	Unknown	Q16678	Homo sapiens
MMDBp0193110	Cytochrome P450 1A1	Unknown	P04798	Homo sapiens
MMDBp0193115	Cytochrome P450 1A2	Unknown	P05177	Homo sapiens
MMDBp0193116	Cytochrome P450 19A1	Unknown	P11511	Homo sapiens
MMDBp0193252	Calmodulin	Unknown	P62158	Homo sapiens
MMDBp0193411	Estrogen receptor	Enzyme	P03372	Homo sapiens
MMDBp0194191	Indoleamine 2,3-dioxygenase 2	Unknown	Q6ZQW0	Homo sapiens
MMDBp0194305	Calreticulin	Unknown	P27797	Homo sapiens
MMDBp0196399	Melatonin receptor type 1A	Unknown	P48039	Homo sapiens
MMDBp0196400	Melatonin receptor type 1B	Unknown	P49286	Homo sapiens
MMDBp0196630	Nuclear receptor ROR-beta	Enzyme	Q92753	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Uremia	Increased	Association	Human Blood	HMDB	12675874

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	1
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva
Bacteria/Eubacteria	Proteobacteria	1
Eukaryota/Fungi	Basidiomycota	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.00140	0.00103			uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	0.000210	5.635e-05			uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0279		0.00	0.0558	uM	Adult (>18 years old)	Both	Normal	HMDB	10960829
Human Urine	Detected and Quantified	0.0000033		0.0000006	0.000006	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.00006	0.000015			uM	Newborn (0-30 days old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.00006	0.000015			uM	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.000063	0.000026			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.00019	0.00015			uM	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.00256	0.00168			uM	Infant (0-1 year old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	0.191	0.201			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal cortex	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal medulla	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Bladder	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Leukocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Ovary	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Pineal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001389

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

References

Synthesis Reference

Not Available

General References

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 ]
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 ]
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. doi: 10.1159/000211518. [PubMed:9449169 ]
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. doi: 10.1034/j.1600-079x.2001.300402.x. [PubMed:11339508 ]
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 ]
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. doi: 10.1016/s0024-3205(01)01143-2. [PubMed:11510949 ]
Bubenik GA: Localization, physiological significance and possible clinical implication of gastrointestinal melatonin. Biol Signals Recept. 2001 Nov-Dec;10(6):350-66. doi: 10.1159/000046903. [PubMed:11721091 ]
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. doi: 10.1097/00006676-200208000-00009. [PubMed:12142740 ]
Bubenik GA: Gastrointestinal melatonin: localization, function, and clinical relevance. Dig Dis Sci. 2002 Oct;47(10):2336-48. doi: 10.1023/a:1020107915919. [PubMed:12395907 ]
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. doi: 10.1002/jcp.10287. [PubMed:12767050 ]
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. doi: 10.1111/j.1749-6632.2003.tb07509.x. [PubMed:12853293 ]
Drake MJ, Mills IW, Noble JG: Melatonin pharmacotherapy for nocturia in men with benign prostatic enlargement. J Urol. 2004 Mar;171(3):1199-202. doi: 10.1097/01.ju.0000110442.47593.ea. [PubMed:14767300 ]
Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. doi: 10.1007/978-1-4615-0135-0_68. [PubMed:15206778 ]
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. doi: 10.1196/annals.1332.014. [PubMed:15681810 ]
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. doi: 10.1111/j.1600-079X.2004.00184.x. [PubMed:15683468 ]
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. doi: 10.1016/j.tips.2005.06.006. [PubMed:15992934 ]
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. doi: 10.1096/fj.04-2293fje. 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. doi: 10.1111/j.1600-079X.2005.00254.x. [PubMed:16150115 ]
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. doi: 10.1111/j.1600-079X.2005.00256.x. [PubMed:16207290 ]
Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. doi: 10.1385/endo:27:2:119. [PubMed:16217125 ]
Nishida S: Metabolic effects of melatonin on oxidative stress and diabetes mellitus. Endocrine. 2005 Jul;27(2):131-6. doi: 10.1385/endo:27:2:131. [PubMed:16217126 ]
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. doi: 10.1097/01.mpa.0000180905.05494.9a. [PubMed:16258371 ]
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Showing metabocard for Melatonin (MMDBc0048361)

MOL for #<Metabolite:0x00007f92518e5dd8>

3D MOL for #<Metabolite:0x00007f92518e5dd8>

3D SDF for #<Metabolite:0x00007f92518e5dd8>

3D-SDF for #<Metabolite:0x00007f92518e5dd8>

PDB for #<Metabolite:0x00007f92518e5dd8>

3D PDB for #<Metabolite:0x00007f92518e5dd8>

SMILES for #<Metabolite:0x00007f92518e5dd8>

INCHI for #<Metabolite:0x00007f92518e5dd8>

Structure for #<Metabolite:0x00007f92518e5dd8>

3D Structure for #<Metabolite:0x00007f92518e5dd8>