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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:56:27 UTC

Update Date

2021-09-14 15:48:21 UTC

HMDB ID

HMDB0060742

Secondary Accession Numbers

HMDB60742

Metabolite Identification

Common Name

3-Hydroxymelatonin

Description

3-Hydroxymelatonin belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. Melatonin Listen/ˌmɛləˈtoʊnɪn/, also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring compound found in animals, plants, and microbes. In animals, circulating levels of the hormone melatonin vary in a daily cycle, thereby allowing the entrainment of the circadian rhythms of several biological functions. 3-Hydroxymelatonin is a strong basic compound (based on its pKa). 3-Hydroxymelatonin is a metabolite of melatonin.

Structure

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

HMDB0060742
     RDKit          3D
3-Hydroxymelatonin
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.0302    2.1874   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284    2.0994   -0.3824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0350    0.8564   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -0.2645   -0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2565   -1.5193   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8932   -1.6117   -0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0210   -0.5062   -0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6463    0.7126   -0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3140   -1.0694   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -1.4650   -1.5001 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -0.3427    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8910    0.8941   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0498    1.5061    0.3771 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2272    1.0298    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956    1.6591    0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163   -0.1190   -0.4737 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807   -2.3903    0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -2.8224   -0.1599 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4362    1.6009   -1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5193    1.8205    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2794    3.2637   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9052   -0.2027   -0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -2.4061   -0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0633    1.6020   -0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5704   -1.6853   -1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472   -1.0550    0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325   -0.2209    1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912    1.5994   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659    0.6212   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2551    0.9744    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7054    2.5911    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0827    1.8826    1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468   -0.2260   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2707   -2.1596    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9079   -3.0853    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3183   -3.7494   -0.5346 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  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  9 17  1  0
 17 18  1  0
  8  3  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv0541 07041311562D          

 18 19  0  0  0  0            999 V2000
    1.8167   -3.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811   -3.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -2.4297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606   -3.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12 11  2  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  4  0  0  0
 14  9  2  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16  9  1  0  0  0  0
 17 13  1  0  0  0  0
 18  2  1  0  0  0  0
 18 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060742

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NCC2(O)CCN=C(C)O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O3/c1-9(16)14-6-5-13(17)8-15-12-4-3-10(18-2)7-11(12)13/h3-4,7,15,17H,5-6,8H2,1-2H3,(H,14,16)

> <INCHI_KEY>
DWMWOUAIGKAJNF-UHFFFAOYSA-N

> <FORMULA>
C13H18N2O3

> <MOLECULAR_WEIGHT>
250.2936

> <EXACT_MASS>
250.131742452

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.129993929396107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(3-hydroxy-5-methoxy-2,3-dihydro-1H-indol-3-yl)ethyl]ethanimidic acid

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.23444041100000068

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.595686904673986

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.541033168058201

> <JCHEM_PKA_STRONGEST_BASIC>
4.847165891860746

> <JCHEM_POLAR_SURFACE_AREA>
74.08000000000001

> <JCHEM_REFRACTIVITY>
69.90240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[2-(3-hydroxy-5-methoxy-1,2-dihydroindol-3-yl)ethyl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060742
     RDKit          3D
3-Hydroxymelatonin
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.0302    2.1874   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284    2.0994   -0.3824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0350    0.8564   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -0.2645   -0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2565   -1.5193   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8932   -1.6117   -0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0210   -0.5062   -0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6463    0.7126   -0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3140   -1.0694   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -1.4650   -1.5001 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -0.3427    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8910    0.8941   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0498    1.5061    0.3771 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2272    1.0298    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956    1.6591    0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163   -0.1190   -0.4737 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807   -2.3903    0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -2.8224   -0.1599 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4362    1.6009   -1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5193    1.8205    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2794    3.2637   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9052   -0.2027   -0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -2.4061   -0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0633    1.6020   -0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5704   -1.6853   -1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472   -1.0550    0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325   -0.2209    1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912    1.5994   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659    0.6212   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2551    0.9744    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7054    2.5911    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0827    1.8826    1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468   -0.2260   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2707   -2.1596    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9079   -3.0853    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3183   -3.7494   -0.5346 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  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  9 17  1  0
 17 18  1  0
  8  3  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       3.391  -7.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.949  -1.883   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.044  -3.129   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.765  -5.781   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.670  -4.535   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       1.233  -5.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.989  -1.246   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   18                                                            
CONECT    3    4   10                                                       
CONECT    4    3   12                                                       
CONECT    5    6   13                                                       
CONECT    6    5   14                                                       
CONECT    7   10   11                                                       
CONECT    8   13   15                                                       
CONECT    9    1   14   16                                                  
CONECT   10    3    7   18                                                  
CONECT   11    7   12   13                                                  
CONECT   12    4   11   15                                                  
CONECT   13    5    8   11   17                                             
CONECT   14    6    9                                                       
CONECT   15    8   12                                                       
CONECT   16    9                                                            
CONECT   17   13                                                            
CONECT   18    2   10                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0060742
HETATM    1  C1  UNL     1      -5.030   2.187  -0.466  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.628   2.099  -0.382  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.035   0.856  -0.338  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.821  -0.265  -0.376  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.256  -1.519  -0.333  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.893  -1.612  -0.251  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.021  -0.506  -0.209  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.646   0.713  -0.255  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.314  -1.069  -0.144  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.607  -1.465  -1.500  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.454  -0.343   0.397  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.891   0.894  -0.272  1.00  0.00           C  
HETATM   13  N1  UNL     1       3.050   1.506   0.377  1.00  0.00           N  
HETATM   14  C11 UNL     1       4.227   1.030   0.280  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.396   1.659   0.944  1.00  0.00           C  
HETATM   16  O3  UNL     1       4.416  -0.119  -0.474  1.00  0.00           O  
HETATM   17  C13 UNL     1       0.081  -2.390   0.608  1.00  0.00           C  
HETATM   18  N2  UNL     1      -1.106  -2.822  -0.160  1.00  0.00           N  
HETATM   19  H1  UNL     1      -5.436   1.601  -1.328  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.519   1.821   0.443  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.279   3.264  -0.611  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.905  -0.203  -0.441  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.911  -2.406  -0.366  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.063   1.602  -0.219  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.570  -1.685  -1.490  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.347  -1.055   0.342  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.333  -0.221   1.511  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.091   1.599  -0.426  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.266   0.621  -1.299  1.00  0.00           H  
HETATM   30  H12 UNL     1       6.255   0.974   0.994  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.705   2.591   0.435  1.00  0.00           H  
HETATM   32  H14 UNL     1       5.083   1.883   1.991  1.00  0.00           H  
HETATM   33  H15 UNL     1       4.147  -0.226  -1.424  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.271  -2.160   1.611  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.908  -3.085   0.509  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.318  -3.749  -0.535  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   22
CONECT    5    6    6   23
CONECT    6    7   18
CONECT    7    8    8    9
CONECT    8   24
CONECT    9   10   11   17
CONECT   10   25
CONECT   11   12   26   27
CONECT   12   13   28   29
CONECT   13   14   14
CONECT   14   15   16
CONECT   15   30   31   32
CONECT   16   33
CONECT   17   18   34   35
CONECT   18   36
END

HMDB0060742
     RDKit          3D
3-Hydroxymelatonin
 36 37  0  0  0  0  0  0  0  0999 V2000
   -5.0302    2.1874   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284    2.0994   -0.3824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0350    0.8564   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -0.2645   -0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2565   -1.5193   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8932   -1.6117   -0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0210   -0.5062   -0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6463    0.7126   -0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3140   -1.0694   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -1.4650   -1.5001 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -0.3427    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8910    0.8941   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0498    1.5061    0.3771 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2272    1.0298    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956    1.6591    0.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163   -0.1190   -0.4737 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807   -2.3903    0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -2.8224   -0.1599 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4362    1.6009   -1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5193    1.8205    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2794    3.2637   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9052   -0.2027   -0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -2.4061   -0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0633    1.6020   -0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5704   -1.6853   -1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472   -1.0550    0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325   -0.2209    1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912    1.5994   -0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659    0.6212   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2551    0.9744    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7054    2.5911    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0827    1.8826    1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468   -0.2260   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2707   -2.1596    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9079   -3.0853    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3183   -3.7494   -0.5346 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  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  9 17  1  0
 17 18  1  0
  8  3  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈N₂O₃

Average Molecular Weight

250.2936

Monoisotopic Molecular Weight

250.131742452

IUPAC Name

N-[2-(3-hydroxy-5-methoxy-2,3-dihydro-1H-indol-3-yl)ethyl]ethanimidic acid

Traditional Name

N-[2-(3-hydroxy-5-methoxy-1,2-dihydroindol-3-yl)ethyl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(NCC2(O)CCN=C(C)O)C=C1

InChI Identifier

InChI=1S/C13H18N2O3/c1-9(16)14-6-5-13(17)8-15-12-4-3-10(18-2)7-11(12)13/h3-4,7,15,17H,5-6,8H2,1-2H3,(H,14,16)

InChI Key

DWMWOUAIGKAJNF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Substituents

Dihydroindole
Anisole
Alkyl aryl ether
Secondary aliphatic/aromatic amine
Aralkylamine
Benzenoid
Tertiary alcohol
1,2-aminoalcohol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Azacycle
Carboximidic acid
Carboximidic acid derivative
Ether
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Amine
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060742)
Liver (HMDB: HMDB0060742)

Biofluid or Excreta

Non-excretory biofluid

Blood (HMDB: HMDB0060742)

Excreta

Urine (HMDB: HMDB0060742)

Cellular substructure

Cytoplasm (HMDB: HMDB0060742)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	0.49 g/L	ALOGPS
logP	0.9	ALOGPS
logP	0.23	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.54	ChemAxon
pKa (Strongest Basic)	4.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	74.08 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.9 m³·mol⁻¹	ChemAxon
Polarizability	27.13 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]+	158.163	31661259
DarkChem	[M-H]-	156.369	31661259
DeepCCS	[M+H]+	158.837	30932474
DeepCCS	[M-H]-	156.479	30932474
DeepCCS	[M-2H]-	189.366	30932474
DeepCCS	[M+Na]+	164.93	30932474
AllCCS	[M+H]+	157.6	32859911
AllCCS	[M+H-H2O]+	153.9	32859911
AllCCS	[M+NH4]+	161.0	32859911
AllCCS	[M+Na]+	161.9	32859911
AllCCS	[M-H]-	161.5	32859911
AllCCS	[M+Na-2H]-	161.7	32859911
AllCCS	[M+HCOO]-	162.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxymelatonin	COC1=CC2=C(NCC2(O)CCN=C(C)O)C=C1	3709.6	Standard polar	33892256
3-Hydroxymelatonin	COC1=CC2=C(NCC2(O)CCN=C(C)O)C=C1	2371.5	Standard non polar	33892256
3-Hydroxymelatonin	COC1=CC2=C(NCC2(O)CCN=C(C)O)C=C1	2432.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxymelatonin,1TMS,isomer #1	COC1=CC=C2NCC(CCN=C(C)O)(O[Si](C)(C)C)C2=C1	2355.7	Semi standard non polar	33892256
3-Hydroxymelatonin,1TMS,isomer #2	COC1=CC=C2NCC(O)(CCN=C(C)O[Si](C)(C)C)C2=C1	2338.8	Semi standard non polar	33892256
3-Hydroxymelatonin,1TMS,isomer #3	COC1=CC=C2C(=C1)C(O)(CCN=C(C)O)CN2[Si](C)(C)C	2416.3	Semi standard non polar	33892256
3-Hydroxymelatonin,2TMS,isomer #1	COC1=CC=C2NCC(CCN=C(C)O[Si](C)(C)C)(O[Si](C)(C)C)C2=C1	2393.6	Semi standard non polar	33892256
3-Hydroxymelatonin,2TMS,isomer #2	COC1=CC=C2C(=C1)C(CCN=C(C)O)(O[Si](C)(C)C)CN2[Si](C)(C)C	2400.8	Semi standard non polar	33892256
3-Hydroxymelatonin,2TMS,isomer #3	COC1=CC=C2C(=C1)C(O)(CCN=C(C)O[Si](C)(C)C)CN2[Si](C)(C)C	2375.2	Semi standard non polar	33892256
3-Hydroxymelatonin,3TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN=C(C)O[Si](C)(C)C)(O[Si](C)(C)C)CN2[Si](C)(C)C	2381.1	Semi standard non polar	33892256
3-Hydroxymelatonin,3TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN=C(C)O[Si](C)(C)C)(O[Si](C)(C)C)CN2[Si](C)(C)C	2314.0	Standard non polar	33892256
3-Hydroxymelatonin,3TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN=C(C)O[Si](C)(C)C)(O[Si](C)(C)C)CN2[Si](C)(C)C	2596.6	Standard polar	33892256
3-Hydroxymelatonin,1TBDMS,isomer #1	COC1=CC=C2NCC(CCN=C(C)O)(O[Si](C)(C)C(C)(C)C)C2=C1	2586.7	Semi standard non polar	33892256
3-Hydroxymelatonin,1TBDMS,isomer #2	COC1=CC=C2NCC(O)(CCN=C(C)O[Si](C)(C)C(C)(C)C)C2=C1	2592.2	Semi standard non polar	33892256
3-Hydroxymelatonin,1TBDMS,isomer #3	COC1=CC=C2C(=C1)C(O)(CCN=C(C)O)CN2[Si](C)(C)C(C)(C)C	2633.0	Semi standard non polar	33892256
3-Hydroxymelatonin,2TBDMS,isomer #1	COC1=CC=C2NCC(CCN=C(C)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C2=C1	2783.9	Semi standard non polar	33892256
3-Hydroxymelatonin,2TBDMS,isomer #2	COC1=CC=C2C(=C1)C(CCN=C(C)O)(O[Si](C)(C)C(C)(C)C)CN2[Si](C)(C)C(C)(C)C	2850.5	Semi standard non polar	33892256
3-Hydroxymelatonin,2TBDMS,isomer #3	COC1=CC=C2C(=C1)C(O)(CCN=C(C)O[Si](C)(C)C(C)(C)C)CN2[Si](C)(C)C(C)(C)C	2836.0	Semi standard non polar	33892256
3-Hydroxymelatonin,3TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN=C(C)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)CN2[Si](C)(C)C(C)(C)C	3024.9	Semi standard non polar	33892256
3-Hydroxymelatonin,3TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN=C(C)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)CN2[Si](C)(C)C(C)(C)C	2933.5	Standard non polar	33892256
3-Hydroxymelatonin,3TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN=C(C)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)CN2[Si](C)(C)C(C)(C)C	2898.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxymelatonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001u-7960000000-23ab131bcce0e20f6309	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxymelatonin GC-MS (2 TMS) - 70eV, Positive	splash10-004i-7449000000-5b21c4e8d77836b42c90	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 10V, Positive-QTOF	splash10-0pb9-0190000000-06521ff602616ccbb8c2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 20V, Positive-QTOF	splash10-0a4l-1960000000-1b8cbdb62f5e4bdd0b54	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 40V, Positive-QTOF	splash10-01pc-2900000000-3111599ee44fd43addff	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 10V, Negative-QTOF	splash10-0002-0290000000-f73bee63e81bcca86f3b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 20V, Negative-QTOF	splash10-0a4i-3980000000-f5a42f5d4dcf35b91520	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 40V, Negative-QTOF	splash10-0a4l-9500000000-76c68b5db7fdc13ddcee	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 10V, Positive-QTOF	splash10-0udl-0590000000-4901f82985f7dc25b410	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 20V, Positive-QTOF	splash10-03di-0930000000-69732fb242d132965ebe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 40V, Positive-QTOF	splash10-00di-1900000000-cd245581f7a9206d34f3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 10V, Negative-QTOF	splash10-052b-0090000000-cb5e935bc3f898ff3c3d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 20V, Negative-QTOF	splash10-0a4i-0790000000-2f3c2cf16e8dbac31248	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymelatonin 40V, Negative-QTOF	splash10-0006-7910000000-0c652c828a3df0741499	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131769936

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3-Hydroxymelatonin (HMDB0060742)

MOL for HMDB0060742 (3-Hydroxymelatonin)

3D MOL for HMDB0060742 (3-Hydroxymelatonin)

3D SDF for HMDB0060742 (3-Hydroxymelatonin)

3D-SDF for HMDB0060742 (3-Hydroxymelatonin)

PDB for HMDB0060742 (3-Hydroxymelatonin)

3D PDB for HMDB0060742 (3-Hydroxymelatonin)

SMILES for HMDB0060742 (3-Hydroxymelatonin)

INCHI for HMDB0060742 (3-Hydroxymelatonin)

Structure for HMDB0060742 (3-Hydroxymelatonin)

3D Structure for HMDB0060742 (3-Hydroxymelatonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra