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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (24) Show 24 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 10:28:32 UTC

Update Date

2020-02-26 21:24:57 UTC

HMDB ID

HMDB0004081

Secondary Accession Numbers

HMDB04081

Metabolite Identification

Common Name

6-Hydroxymelatonin

Description

6-Hydroxymelatonin, also known as lopac-H-0627, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 6-Hydroxymelatonin is considered to be a practically insoluble (in water) and relatively neutral molecule. 6-Hydroxymelatonin has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, 6-hydroxymelatonin is primarily located in the cytoplasm. 6-Hydroxymelatonin is the main primary metabolite that can be biosynthesized from melatonin through its interaction with the enzyme cytochrome P450 (CYP) 1A2 (PMID: 11452239 ). In humans, 6-hydroxymelatonin is involved in the tryptophan metabolism pathway.

Structure

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

HMDB0004081
     RDKit          3D
6-Hydroxymelatonin
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.3409    2.0353   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810    0.6130   -0.4372 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522   -0.1829   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438    0.3889    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9982   -0.3443    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -0.0092    0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    1.3692    0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860    1.3424    1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430    0.6992    0.1841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4475    0.5171    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1843   -0.1574   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0773    0.9459    1.2142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9529   -1.2172    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906   -2.2193    0.5821 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1506   -1.7166    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3518   -2.3104   -0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4653   -1.5526   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7003   -2.1284   -0.5663 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327    2.5090   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    2.3808   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194    2.3219    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131    1.4797    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070    1.9001    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357    1.9413   -0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3813    0.7690    2.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142    2.4034    1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5380    0.3279   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1242   -1.2560   -0.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2560    0.1511   -0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7300    0.1023   -1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014   -1.3315    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -3.2528    0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -3.3813   -0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7472   -3.1375   -0.6058 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  6 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
 15  5  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 18 34  1  0
M  END


  Mrv0541 02231219522D          

 18 19  0  0  0  0            999 V2000
   25.6576  -12.0198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6576  -13.6699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2599  -10.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9016  -10.4424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5817  -13.5087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6454  -11.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8381  -11.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6576  -11.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9652   -9.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7089  -10.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3721  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3721  -12.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8011  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5817  -12.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8011  -12.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0632  -12.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0867  -13.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0867  -12.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 12  1  0  0  0  0
  2 11  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  1  0  0  0  0
  4 10  1  0  0  0  0
  5 13  1  0  0  0  0
  5 16  1  0  0  0  0
  6  7  1  0  0  0  0
  7 14  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  1  0  0  0  0
 13 15  1  0  0  0  0
 13 17  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004081

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)

> <INCHI_KEY>
OMYMRCXOJJZYKE-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O3

> <MOLECULAR_WEIGHT>
248.2777

> <EXACT_MASS>
248.116092388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.646859447844083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
0.8440474656666671

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.88686461347585

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.293899803560572

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9409566074830477

> <JCHEM_POLAR_SURFACE_AREA>
74.35

> <JCHEM_REFRACTIVITY>
68.26080000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004081
     RDKit          3D
6-Hydroxymelatonin
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.3409    2.0353   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810    0.6130   -0.4372 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522   -0.1829   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438    0.3889    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9982   -0.3443    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -0.0092    0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    1.3692    0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860    1.3424    1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430    0.6992    0.1841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4475    0.5171    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1843   -0.1574   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0773    0.9459    1.2142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9529   -1.2172    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906   -2.2193    0.5821 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1506   -1.7166    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3518   -2.3104   -0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4653   -1.5526   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7003   -2.1284   -0.5663 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327    2.5090   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    2.3808   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194    2.3219    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131    1.4797    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070    1.9001    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357    1.9413   -0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3813    0.7690    2.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142    2.4034    1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5380    0.3279   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1242   -1.2560   -0.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2560    0.1511   -0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7300    0.1023   -1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014   -1.3315    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -3.2528    0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -3.3813   -0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7472   -3.1375   -0.6058 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  6 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
 15  5  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      47.894 -22.437   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      47.894 -25.517   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      58.352 -20.321   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      55.816 -19.492   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      53.353 -25.216   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      55.338 -20.956   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      53.831 -21.274   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.894 -20.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      57.802 -17.711   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      57.323 -19.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      49.228 -24.747   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.228 -23.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.895 -24.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.353 -22.738   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      51.895 -23.207   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      54.251 -23.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      50.562 -25.517   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      50.562 -22.437   0.000  0.00  0.00           C+0
CONECT    1    8   12                                                       
CONECT    2   11                                                            
CONECT    3   10                                                            
CONECT    4    6   10                                                       
CONECT    5   13   16                                                       
CONECT    6    4    7                                                       
CONECT    7    6   14                                                       
CONECT    8    1                                                            
CONECT    9   10                                                            
CONECT   10    3    4    9                                                  
CONECT   11    2   12   17                                                  
CONECT   12    1   11   18                                                  
CONECT   13    5   15   17                                                  
CONECT   14    7   15   16                                                  
CONECT   15   13   14   18                                                  
CONECT   16    5   14                                                       
CONECT   17   11   13                                                       
CONECT   18   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0004081
HETATM    1  C1  UNL     1       4.341   2.035  -0.364  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.481   0.613  -0.437  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.352  -0.183  -0.188  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.144   0.389   0.118  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.998  -0.344   0.373  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.303  -0.009   0.695  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.836   1.369   0.861  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.286   1.342   1.208  1.00  0.00           C  
HETATM    9  N1  UNL     1      -3.043   0.699   0.184  1.00  0.00           N  
HETATM   10  C8  UNL     1      -4.448   0.517   0.221  1.00  0.00           C  
HETATM   11  C9  UNL     1      -5.184  -0.157  -0.868  1.00  0.00           C  
HETATM   12  O2  UNL     1      -5.077   0.946   1.214  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.953  -1.217   0.817  1.00  0.00           C  
HETATM   14  N2  UNL     1      -0.091  -2.219   0.582  1.00  0.00           N  
HETATM   15  C11 UNL     1       1.151  -1.717   0.298  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.352  -2.310  -0.007  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.465  -1.553  -0.254  1.00  0.00           C  
HETATM   18  O3  UNL     1       4.700  -2.128  -0.566  1.00  0.00           O  
HETATM   19  H1  UNL     1       5.333   2.509  -0.432  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.668   2.381  -1.147  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.919   2.322   0.634  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.013   1.480   0.180  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.307   1.900   1.703  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.636   1.941  -0.068  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.381   0.769   2.176  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.614   2.403   1.351  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.538   0.328  -0.665  1.00  0.00           H  
HETATM   28  H10 UNL     1      -5.124  -1.256  -0.673  1.00  0.00           H  
HETATM   29  H11 UNL     1      -6.256   0.151  -0.831  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.730   0.102  -1.853  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.001  -1.331   1.066  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.293  -3.253   0.602  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.436  -3.381  -0.057  1.00  0.00           H  
HETATM   34  H16 UNL     1       4.747  -3.137  -0.606  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   22
CONECT    5    6   15   15
CONECT    6    7   13   13
CONECT    7    8   23   24
CONECT    8    9   25   26
CONECT    9   10   27
CONECT   10   11   12   12
CONECT   11   28   29   30
CONECT   13   14   31
CONECT   14   15   32
CONECT   15   16
CONECT   16   17   17   33
CONECT   17   18
CONECT   18   34
END

HMDB0004081
     RDKit          3D
6-Hydroxymelatonin
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.3409    2.0353   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810    0.6130   -0.4372 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522   -0.1829   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438    0.3889    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9982   -0.3443    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -0.0092    0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    1.3692    0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860    1.3424    1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430    0.6992    0.1841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4475    0.5171    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1843   -0.1574   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0773    0.9459    1.2142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9529   -1.2172    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906   -2.2193    0.5821 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1506   -1.7166    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3518   -2.3104   -0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4653   -1.5526   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7003   -2.1284   -0.5663 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327    2.5090   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    2.3808   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194    2.3219    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131    1.4797    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070    1.9001    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357    1.9413   -0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3813    0.7690    2.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142    2.4034    1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5380    0.3279   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1242   -1.2560   -0.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2560    0.1511   -0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7300    0.1023   -1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014   -1.3315    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929   -3.2528    0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -3.3813   -0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7472   -3.1375   -0.6058 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  6 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
 15  5  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lopac-H-0627	ChEBI
6-Oxymelatonin	HMDB
6-Hydroxy-N-acetyl-5-methoxytryptamine	HMDB
6-Hydroxy-N-acetyl-5-methoxytryptamine	HMDB

Chemical Formula

C₁₃H₁₆N₂O₃

Average Molecular Weight

248.2777

Monoisotopic Molecular Weight

248.116092388

IUPAC Name

N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

Traditional Name

N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

CAS Registry Number

2208-41-5

SMILES

COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1

InChI Identifier

InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)

InChI Key

OMYMRCXOJJZYKE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents

Substituents

Hydroxyindole
3-alkylindole
Indole
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Azacycle
Ether
Carboximidic acid derivative
Carboximidic acid
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acetamides (CHEBI:2198 )
tryptamines (CHEBI:2198 )
a small molecule (CPD-12014 )

Ontology

Not Available

Blood (HMDB: HMDB0004081)
Urine (HMDB: HMDB0004081)

Organ substructure

Adrenal Medulla (HMDB: HMDB0004081)

Organ

Liver (HMDB: HMDB0004081)
Kidney (HMDB: HMDB0004081)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8255371)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0004081)

Cellular substructure

Cytoplasm (HMDB: HMDB0004081)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004081)

Source

Endogenous

Endogenous (HMDB: HMDB0004081)

Plant

Animal

Animal (HMDB: HMDB0004081)

Exogenous

Food

Food (HMDB: HMDB0004081)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

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)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (HMDB: HMDB0004081)

Tryptophan Metabolism (HMDB: HMDB0004081)

Role

Biological role

Drug metabolite (HMDB: HMDB0004081)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	0.8	ALOGPS
logP	0.84	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-0.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	74.35 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.26 m³·mol⁻¹	ChemAxon
Polarizability	26.65 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]+	155.91	31661259
DarkChem	[M-H]-	158.634	31661259
DeepCCS	[M+H]+	158.105	30932474
DeepCCS	[M-H]-	155.747	30932474
DeepCCS	[M-2H]-	188.633	30932474
DeepCCS	[M+Na]+	164.198	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	153.1	32859911
AllCCS	[M+NH4]+	160.2	32859911
AllCCS	[M+Na]+	161.2	32859911
AllCCS	[M-H]-	160.4	32859911
AllCCS	[M+Na-2H]-	160.5	32859911
AllCCS	[M+HCOO]-	160.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxymelatonin	COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1	3864.9	Standard polar	33892256
6-Hydroxymelatonin	COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1	2537.2	Standard non polar	33892256
6-Hydroxymelatonin	COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1	2596.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxymelatonin,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C=C2CCNC(C)=O	2618.3	Semi standard non polar	33892256
6-Hydroxymelatonin,1TMS,isomer #2	COC1=CC2=C(C=C1O)N([Si](C)(C)C)C=C2CCNC(C)=O	2667.8	Semi standard non polar	33892256
6-Hydroxymelatonin,1TMS,isomer #3	COC1=CC2=C(C=C1O)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C	2542.7	Semi standard non polar	33892256
6-Hydroxymelatonin,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C	2542.1	Semi standard non polar	33892256
6-Hydroxymelatonin,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C	2696.7	Standard non polar	33892256
6-Hydroxymelatonin,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C	2934.4	Standard polar	33892256
6-Hydroxymelatonin,2TMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C2CCNC(C)=O	2647.4	Semi standard non polar	33892256
6-Hydroxymelatonin,2TMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C2CCNC(C)=O	2566.2	Standard non polar	33892256
6-Hydroxymelatonin,2TMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C2CCNC(C)=O	2948.3	Standard polar	33892256
6-Hydroxymelatonin,2TMS,isomer #3	COC1=CC2=C(C=C1O)N([Si](C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C	2558.6	Semi standard non polar	33892256
6-Hydroxymelatonin,2TMS,isomer #3	COC1=CC2=C(C=C1O)N([Si](C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C	2783.4	Standard non polar	33892256
6-Hydroxymelatonin,2TMS,isomer #3	COC1=CC2=C(C=C1O)N([Si](C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C	2986.3	Standard polar	33892256
6-Hydroxymelatonin,3TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C	2593.0	Semi standard non polar	33892256
6-Hydroxymelatonin,3TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C	2690.1	Standard non polar	33892256
6-Hydroxymelatonin,3TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C	2753.6	Standard polar	33892256
6-Hydroxymelatonin,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C=C2CCNC(C)=O	2877.6	Semi standard non polar	33892256
6-Hydroxymelatonin,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C=C2CCNC(C)=O	2903.1	Semi standard non polar	33892256
6-Hydroxymelatonin,1TBDMS,isomer #3	COC1=CC2=C(C=C1O)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C	2786.9	Semi standard non polar	33892256
6-Hydroxymelatonin,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C	3009.7	Semi standard non polar	33892256
6-Hydroxymelatonin,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C	3118.4	Standard non polar	33892256
6-Hydroxymelatonin,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C	3087.6	Standard polar	33892256
6-Hydroxymelatonin,2TBDMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C2CCNC(C)=O	3127.7	Semi standard non polar	33892256
6-Hydroxymelatonin,2TBDMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C2CCNC(C)=O	2997.5	Standard non polar	33892256
6-Hydroxymelatonin,2TBDMS,isomer #2	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C2CCNC(C)=O	3072.9	Standard polar	33892256
6-Hydroxymelatonin,2TBDMS,isomer #3	COC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C	3011.4	Semi standard non polar	33892256
6-Hydroxymelatonin,2TBDMS,isomer #3	COC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C	3153.0	Standard non polar	33892256
6-Hydroxymelatonin,2TBDMS,isomer #3	COC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C	3088.6	Standard polar	33892256
6-Hydroxymelatonin,3TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C	3225.4	Semi standard non polar	33892256
6-Hydroxymelatonin,3TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C	3276.9	Standard non polar	33892256
6-Hydroxymelatonin,3TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C=C2CCN(C(C)=O)[Si](C)(C)C(C)(C)C	3030.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 6-Hydroxymelatonin GC-MS (3 TMS)	splash10-00di-1659000000-71cdfc5bdcf432c9a84a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 6-Hydroxymelatonin GC-MS (Non-derivatized)	splash10-00di-1659000000-71cdfc5bdcf432c9a84a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxymelatonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9670000000-71b021cf86103b186db2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxymelatonin GC-MS (1 TMS) - 70eV, Positive	splash10-05fv-7093000000-311814a60377cf77abd4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxymelatonin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Hydroxymelatonin LC-ESI-qTof , Positive-QTOF	splash10-0a4i-3900000000-533a23d884233d4fd905	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Hydroxymelatonin , positive-QTOF	splash10-0a4i-3900000000-533a23d884233d4fd905	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 10V, Positive-QTOF	splash10-0a4j-0190000000-fc098aa93958c18074a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 20V, Positive-QTOF	splash10-0a4i-0970000000-669a6bd5f7e0091b9ca4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 40V, Positive-QTOF	splash10-03fu-1900000000-ffc8f8f8477bce088493	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 10V, Negative-QTOF	splash10-0002-1090000000-b17e668c7f1e41db8d30	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 20V, Negative-QTOF	splash10-0a4i-3490000000-92983db3c1d0bece458c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 40V, Negative-QTOF	splash10-052f-9200000000-3ac4e7417916c5b2e2f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 10V, Positive-QTOF	splash10-0006-0920000000-7ed799d3e8693bde62e7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 20V, Positive-QTOF	splash10-0006-0910000000-eb01005068ed6043a454	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 40V, Positive-QTOF	splash10-08fu-0900000000-2d6ad727babdb3e4bb6e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 10V, Negative-QTOF	splash10-0002-0090000000-dff205e638af0877604b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 20V, Negative-QTOF	splash10-0a4l-9200000000-d8c0a556f4b94d832017	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxymelatonin 40V, Negative-QTOF	splash10-06r5-4940000000-23e212544ac34c9c55d6	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Adrenal Medulla
Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00024 (0.00008-0.0004) uM	Adult (>18 years old)	Both	Normal	8255371	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023304

KNApSAcK ID

Not Available

Chemspider ID

1794

KEGG Compound ID

C05643

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

2198

Food Biomarker Ontology

Not Available

VMH ID

6HOXMELATN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Karam, Omar; Zunino, Fabien; Chagnaut, Vincent; Jouannetaud, Marie Paule; Jacquesy, Jean Claude. An efficient synthesis of 6-hydroxymelatonin, a human metabolite of melatonin. Tetrahedron Letters (2003), 44(7), 1511-1513.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Higa S, Suzuki T, Sakoda S, Kishimoto S, Takaba Y, Nakajima A, Markey SP: Disturbed function of the pineal gland in familial amyloid polyneuropathy. J Neural Transm. 1987;69(1-2):97-103. [PubMed:3035087 ]
Bojkowski CJ, Arendt J, Shih MC, Markey SP: Melatonin secretion in humans assessed by measuring its metabolite, 6-sulfatoxymelatonin. Clin Chem. 1987 Aug;33(8):1343-8. [PubMed:3608151 ]
Whitson PA, Putcha L, Chen YM, Baker E: Melatonin and cortisol assessment of circadian shifts in astronauts before flight. J Pineal Res. 1995 Apr;18(3):141-7. [PubMed:7562371 ]
Nowak R, McMillen IC, Redman J, Short RV: The correlation between serum and salivary melatonin concentrations and urinary 6-hydroxymelatonin sulphate excretion rates: two non-invasive techniques for monitoring human circadian rhythmicity. Clin Endocrinol (Oxf). 1987 Oct;27(4):445-52. [PubMed:3436070 ]
Bruce J, Tamarkin L, Riedel C, Markey S, Oldfield E: Sequential cerebrospinal fluid and plasma sampling in humans: 24-hour melatonin measurements in normal subjects and after peripheral sympathectomy. J Clin Endocrinol Metab. 1991 Apr;72(4):819-23. [PubMed:2005207 ]
Francis PL, Leone AM, Young IM, Stovell P, Silman RE: Gas chromatographic-mass spectrometric assay for 6-hydroxymelatonin sulfate and 6-hydroxymelatonin glucuronide in urine. Clin Chem. 1987 Apr;33(4):453-7. [PubMed:3829375 ]
Hartter S, Ursing C, Morita S, Tybring G, von Bahr C, Christensen M, Rojdmark S, Bertilsson L: Orally given melatonin may serve as a probe drug for cytochrome P450 1A2 activity in vivo: a pilot study. Clin Pharmacol Ther. 2001 Jul;70(1):10-6. [PubMed:11452239 ]

Only showing the first 10 proteins. There are 24 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. 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

Enzyme Details

3. 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

Enzyme Details

4. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

Enzyme Details

5. Cytochrome P450 3A43

General function:: Involved in monooxygenase activity
Specific function:: Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:: CYP3A43
Uniprot ID:: Q9HB55
Molecular weight:: 57756.285

Enzyme Details

6. 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

Enzyme Details

7. Cytochrome P450 2C18

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:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

Enzyme Details

8. Cytochrome P450 2F1

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:: CYP2F1
Uniprot ID:: P24903
Molecular weight:: 55500.64

Enzyme Details

9. Cytochrome P450 4X1

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP4X1
Uniprot ID:: Q8N118
Molecular weight:: 58874.62

Enzyme Details

10. Cytochrome P450 2B6

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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

Only showing the first 10 proteins. There are 24 proteins in total.

Show all enzymes and transporters

Showing metabocard for 6-Hydroxymelatonin (HMDB0004081)

MOL for HMDB0004081 (6-Hydroxymelatonin)

3D MOL for HMDB0004081 (6-Hydroxymelatonin)

3D SDF for HMDB0004081 (6-Hydroxymelatonin)

3D-SDF for HMDB0004081 (6-Hydroxymelatonin)

PDB for HMDB0004081 (6-Hydroxymelatonin)

3D PDB for HMDB0004081 (6-Hydroxymelatonin)

SMILES for HMDB0004081 (6-Hydroxymelatonin)

INCHI for HMDB0004081 (6-Hydroxymelatonin)

Structure for HMDB0004081 (6-Hydroxymelatonin)

3D Structure for HMDB0004081 (6-Hydroxymelatonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes