NP-MRD: Showing NP-Card for Melatonin (NP0000673)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:19 UTC

NP-MRD ID

NP0000673

Secondary Accession Numbers

None

Natural Product 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>
NP0000673

> <DATABASE_NAME>
NP-MRD

> <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

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
Melatobel	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 Mass

232.2783 Da

Monoisotopic Mass

232.12118 Da

IUPAC Name

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

Traditional Name

melatonin

CAS Registry Number

73-31-4

SMILES

COC1=CC=C2NC=C(CCNC(C)=O)C2=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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acetabularia acetabulum	KNApSAcK Database	22123792
Agastaches rugosa	-	KNApSAcK
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Aloe vela	KNApSAcK Database	22123792
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Andrographis paniculatus	KNApSAcK Database	22123792
Anethum foeniculum	Plant	KNApSAcK
Angelica biserrata	KNApSAcK Database	22123792
Angelica sinensis	KNApSAcK Database	22123792
Anser anser	FooDB	FooDB
Apium graveolens	KNApSAcK Database	22123792
Arnebia euchroma	KNApSAcK Database	22123792
Artemisis anna	-	KNApSAcK
Avena sativa	KNApSAcK Database	22123792
Avena sativa L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Babreum coscluea	-	KNApSAcK
Baccaurea ramiflora	-	KNApSAcK
Beta vulgaris	KNApSAcK Database	22123792
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica nigra	KNApSAcK Database	22123792
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	PHYTOHUB
Ceratium horridum	-	KNApSAcK
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chenopodium rubrum	KNApSAcK Database	22123792
Chlomydomonas spp.	-	KNApSAcK
Chrysanthemum x morifolium	Plant	KNApSAcK
Cistanche deseriocola	KNApSAcK Database	22123792
Citrus reticulata	KNApSAcK Database	22123792
Coffea arabica	KNApSAcK Database	22123792
Coffea arabica L.	FooDB	PHYTOHUB
Coffea canephora	KNApSAcK Database	22123792
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Coptis chinensis	KNApSAcK Database	22123792
Coriandrum sativum	KNApSAcK Database	22123792
Coriandrum sativum L.	Plant	KNApSAcK
Coruns officinalis	-	KNApSAcK
Cucumis sativus	KNApSAcK Database	22123792
Cucumis sativus L.	Plant	KNApSAcK
Curcuma aeruginosa	KNApSAcK Database	22123792
Datura metel	Plant	KNApSAcK
Dendranthema morifolium	KNApSAcK Database	22123792
Desmodium styracifolium	KNApSAcK Database	22123792
Didymosphaeria mori-albae	-	KNApSAcK
Dromaius novaehollandiae	FooDB	FooDB
Dunaliella teriolecta	KNApSAcK Database	22123792
Elettaria cardamomum	KNApSAcK Database	22123792
Epimedium brevicornum	KNApSAcK Database	22123792
Equus caballus	FooDB	FooDB
Eucommia ulmoides	KNApSAcK Database	22123792
Festuca arundinacea	KNApSAcK Database	22123792
Foeniculum vulgare	KNApSAcK Database	22123792
Forsythia suspensa	KNApSAcK Database	22123792
Fragaria x ananassa	KNApSAcK Database	22123792
Galdenia jasminoides	-	KNApSAcK
Gallus gallus	FooDB	FooDB
Gekko japanicus	-	KNApSAcK
Gentiana macrophylla	KNApSAcK Database	22123792
Gentiana scabra	KNApSAcK Database	22123792
Glycyrrhiza uralensis	KNApSAcK Database	22123792
Gonyaulax polyedra	-	KNApSAcK
Grona styracifolia	Plant	KNApSAcK
Helianthus annuus	KNApSAcK Database	22123792
Helianthus annuus L.	Plant	KNApSAcK
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hypericum perforatum	KNApSAcK Database	22123792
Ipomoea nil	Plant	KNApSAcK
Isatis indigotica	KNApSAcK Database	22123792
Isatis tinctoria	Plant	KNApSAcK
Juglans regia	KNApSAcK Database	22123792
Lagopus muta	FooDB	FooDB
Laminaria digitata	KNApSAcK Database	22123792
Leonurus japonicus	KNApSAcK Database	22123792
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Linum usitatissimum	KNApSAcK Database	22123792
Lobelia chinensis	KNApSAcK Database	22123792
Lonicera japonica	KNApSAcK Database	22123792
Lophartherum gracile	-	KNApSAcK
Lupinus albus	KNApSAcK Database	22123792
Lycium barbarum	KNApSAcK Database	22123792
Mahania bealei	-	KNApSAcK
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mamestra brassicae	LOTUS Database	35616633
Medicago sativum	KNApSAcK Database	22123792
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mesocricetus auratus	LOTUS Database	35616633
Momordica charantia	KNApSAcK Database	22123792
Morus alba	KNApSAcK Database	22123792
Mus musculus	LOTUS Database	35616633
Musa spp.	KNApSAcK Database	22123792
Nicotiana tobacum	KNApSAcK Database	22123792
Noctiluca scintillans	-	KNApSAcK
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Ophiopogon intermedius	LOTUS Database	35616633
Ophiopogon japonicus	KNApSAcK Database	22123792
Oryctolagus	FooDB	FooDB
Oryza sativa japonica	KNApSAcK Database	22123792
Ovis aries	FooDB	FooDB
Panax notoginsneg	KNApSAcK Database	22123792
Papaver somniferum	KNApSAcK Database	22123792
Patrinia scabiosifolia	KNApSAcK Database	22123792
Patriniae scabiosaefoliae	-	KNApSAcK
Periostracum cicadae	-	KNApSAcK
Petalonia fascia	-	KNApSAcK
Petasites japonicus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pharbitis nil	KNApSAcK Database	22123792
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phellodendron amurense	KNApSAcK Database	22123792
Pheretima aspergillum	-	KNApSAcK
Pimpinela anisum	-	KNApSAcK
Piper nigrum	KNApSAcK Database	22123792
Piper nigrum L.	Plant	KNApSAcK
Pirola decorata	-	KNApSAcK
Pistacia vera	FooDB	PHYTOHUB
Polygala tenuifolia	KNApSAcK Database	22123792
Polygonatum sibiricum	KNApSAcK Database	22123792
Polygonum multiflorum	KNApSAcK Database	22123792
Prunella vulgaris	KNApSAcK Database	22123792
Prunus amygdalus	KNApSAcK Database	22123792
Prunus avium	KNApSAcK Database	22123792
Prunus cerasus	KNApSAcK Database	22123792
Prunus dulcis	Plant	KNApSAcK
Pterygophora californica	-	KNApSAcK
Pueraria lobata	KNApSAcK Database	22123792
Punica granatum	KNApSAcK Database	22123792
Pyrocystis lunula	-	KNApSAcK
Raphanus sativus	KNApSAcK Database	22123792
Rehmannia glutinosa	KNApSAcK Database	22123792
Rheum palmatum	KNApSAcK Database	22123792
Rubus chingii	KNApSAcK Database	22123792
Salvia miltiorrhiza	KNApSAcK Database	22123792
Saposhmikovia divaricata	-	KNApSAcK
Schisondra chinensis	-	KNApSAcK
Scrophularia ningpoensis	KNApSAcK Database	22123792
Scutellaria amoena	KNApSAcK Database	22123792
Scutellaria baicalensis	KNApSAcK Database	22123792
Senna tora	KNApSAcK Database	22123792
Sesbania glandiflora	KNApSAcK Database	22123792
Sesbania sesban	KNApSAcK Database	22123792
Silybum marianum	KNApSAcK Database	22123792
Sinapis alba	KNApSAcK Database	22123792
Solanum lycopersicum	KNApSAcK Database	22123792
Sophora flavescens	KNApSAcK Database	22123792
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Syzygium aromaticum	KNApSAcK Database	22123792
Tanacetum parthenium	KNApSAcK Database	22123792
Taxillus chinensis	KNApSAcK Database	22123792
Trigonella foenum-graecum	KNApSAcK Database	22123792
Trypanosoma cruzi	-	KNApSAcK
Uncaria rhynchophylla	KNApSAcK Database	22123792
Viola philipica	KNApSAcK Database	22123792
Vitis	FooDB	PHYTOHUB
Vitis vinifera	KNApSAcK Database	22123792
Vitis vinifera L.	Plant	KNApSAcK
Wolfiporia cocos	-	KNApSAcK
Zea mays	KNApSAcK Database	22123792
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ziziphus jujuba	KNApSAcK Database	22123792

Species Where Detected

Species Name	Source	Reference
Alexandrium lusitanicum	KNApSAcK Database	22123792
Amphidinium carterae	KNApSAcK Database	22123792
Bombyx batryticatus	KNApSAcK Database	22123792
Chondrus crispus	KNApSAcK Database	22123792
Erythrobacter longus	KNApSAcK Database	22123792
Euglena gracilis	KNApSAcK Database	22123792
Gracilaria tenustipitata	KNApSAcK Database	22123792
Homo sapiens	KNApSAcK Database	22123792
Neurospora crassa	KNApSAcK Database	22123792
Palmaria palmata	KNApSAcK Database	22123792
Porphyra umbilicalis	KNApSAcK Database	22123792
Rhodospirillum rubrum	KNApSAcK Database	22123792
Saccharomyces cerevisiae	KNApSAcK Database	22123792
Scolopendra subspinipes	KNApSAcK Database	22123792
Tetrahymena thermophila	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	117 °C	Not Available
Boiling Point	512.83 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1164 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.043 (est)	The Good Scents Company Information System

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

External Links

HMDB ID

HMDB0001389

DrugBank ID

DB01065

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

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

Good Scents ID

rw1256771

References

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 ]
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Showing NP-Card for Melatonin (NP0000673)

MOL for NP0000673 (Melatonin)

3D MOL for NP0000673 (Melatonin)

3D SDF for NP0000673 (Melatonin)

3D-SDF for NP0000673 (Melatonin)

PDB for NP0000673 (Melatonin)

3D PDB for NP0000673 (Melatonin)

SMILES for NP0000673 (Melatonin)

INCHI for NP0000673 (Melatonin)

Structure for NP0000673 (Melatonin)

3D Structure for NP0000673 (Melatonin)