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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-09 20:52:23 UTC

Update Date

2022-03-07 03:17:38 UTC

HMDB ID

HMDB0060070

Secondary Accession Numbers

HMDB60070

Metabolite Identification

Common Name

Melatonin radical

Description

Melatonin radical 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 radical is a strong basic compound (based on its pKa). These are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Structure

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

HMDB0060070
     RDKit          3D
Melatonin radical
 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.6511    0.8713    3.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    0.0540    2.3742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4155   -0.4598    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778   -1.2383    0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613   -1.7361   -0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025   -1.4636   -1.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947   -0.6524   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494   -0.1722    0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0568   -0.6468   -1.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -2.0554   -1.8843 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108    0.2075   -1.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2340    0.0501   -0.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8887    0.2388    0.5897 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490    1.1413    1.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3415    2.1163    0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9191    1.2080    2.6746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788   -0.6444   -3.1375 C   0  0  0  0  0  3  0  0  0  0  0  0
   -1.6116   -1.8074   -2.7412 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0597    1.3794    3.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3075    1.7018    2.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8088    0.2333    3.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3083   -1.4959    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -2.3712   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128    0.4843    0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6748   -2.3085   -0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9237    1.3240   -1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    0.0670   -2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309   -0.9746   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417    0.7216   -1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    2.9146    1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2887    1.5590    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0191    2.5955   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4525    1.5420    3.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    0.2496   -3.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511   -2.6329   -3.2624 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
 18 35  1  0
M  RAD  1  17   2
M  END

  Mrv0541 05091313522D          

 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  RAD  1   8   2
M  END
> <DATABASE_ID>
HMDB0060070

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(N[CH]C2(O)CCN=C(C)O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H17N2O3/c1-9(16)14-6-5-13(17)8-15-12-4-3-10(18-2)7-11(12)13/h3-4,7-8,15,17H,5-6H2,1-2H3,(H,14,16)

> <INCHI_KEY>
SQNQBXWYHXYLQX-UHFFFAOYSA-N

> <FORMULA>
C13H17N2O3

> <MOLECULAR_WEIGHT>
249.2857

> <EXACT_MASS>
249.12391742

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.83763139001082

> <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>
0.6826570886666667

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.339773079723297

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.487913287517757

> <JCHEM_PKA_STRONGEST_BASIC>
4.73410851086343

> <JCHEM_POLAR_SURFACE_AREA>
74.08000000000001

> <JCHEM_REFRACTIVITY>
70.00970000000001

> <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

$$$$

HMDB0060070
     RDKit          3D
Melatonin radical
 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.6511    0.8713    3.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    0.0540    2.3742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4155   -0.4598    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778   -1.2383    0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613   -1.7361   -0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025   -1.4636   -1.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947   -0.6524   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494   -0.1722    0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0568   -0.6468   -1.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -2.0554   -1.8843 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108    0.2075   -1.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2340    0.0501   -0.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8887    0.2388    0.5897 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490    1.1413    1.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3415    2.1163    0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9191    1.2080    2.6746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788   -0.6444   -3.1375 C   0  0  0  0  0  3  0  0  0  0  0  0
   -1.6116   -1.8074   -2.7412 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0597    1.3794    3.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3075    1.7018    2.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8088    0.2333    3.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3083   -1.4959    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -2.3712   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128    0.4843    0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6748   -2.3085   -0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9237    1.3240   -1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    0.0670   -2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309   -0.9746   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417    0.7216   -1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    2.9146    1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2887    1.5590    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0191    2.5955   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4525    1.5420    3.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    0.2496   -3.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511   -2.6329   -3.2624 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
 18 35  1  0
M  RAD  1  17   2
M  END

HEADER    PROTEIN                                 09-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAY-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    HMDB0060070
HETATM    1  C1  UNL     1      -1.651   0.871   3.009  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.620   0.054   2.374  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.415  -0.460   1.102  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.378  -1.238   0.538  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.161  -1.736  -0.718  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.002  -1.464  -1.405  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.995  -0.652  -0.812  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.249  -0.172   0.441  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.057  -0.647  -1.834  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.546  -2.055  -1.884  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.211   0.207  -1.832  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.234   0.050  -0.761  1.00  0.00           C  
HETATM   13  N1  UNL     1       1.889   0.239   0.590  1.00  0.00           N  
HETATM   14  C11 UNL     1       2.349   1.141   1.368  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.342   2.116   0.876  1.00  0.00           C  
HETATM   16  O3  UNL     1       1.919   1.208   2.675  1.00  0.00           O  
HETATM   17  C13 UNL     1      -0.779  -0.644  -3.137  1.00  0.00           C  
HETATM   18  N2  UNL     1      -1.612  -1.807  -2.741  1.00  0.00           N  
HETATM   19  H1  UNL     1      -2.060   1.379   3.902  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.308   1.702   2.334  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.809   0.233   3.346  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.308  -1.496   1.011  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.951  -2.371  -1.171  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.513   0.484   0.906  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.675  -2.308  -0.929  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.924   1.324  -1.919  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.775   0.067  -2.813  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.731  -0.975  -0.830  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.142   0.722  -1.008  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.543   2.915   1.615  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.289   1.559   0.694  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.019   2.595  -0.080  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.452   1.542   3.452  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.432   0.250  -3.093  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.851  -2.633  -3.262  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
CONECT   18   35
END

HMDB0060070
     RDKit          3D
Melatonin radical
 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.6511    0.8713    3.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    0.0540    2.3742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4155   -0.4598    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778   -1.2383    0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613   -1.7361   -0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025   -1.4636   -1.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947   -0.6524   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494   -0.1722    0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0568   -0.6468   -1.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -2.0554   -1.8843 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108    0.2075   -1.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2340    0.0501   -0.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8887    0.2388    0.5897 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490    1.1413    1.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3415    2.1163    0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9191    1.2080    2.6746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788   -0.6444   -3.1375 C   0  0  0  0  0  3  0  0  0  0  0  0
   -1.6116   -1.8074   -2.7412 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0597    1.3794    3.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3075    1.7018    2.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8088    0.2333    3.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3083   -1.4959    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -2.3712   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128    0.4843    0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6748   -2.3085   -0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9237    1.3240   -1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    0.0670   -2.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309   -0.9746   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417    0.7216   -1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    2.9146    1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2887    1.5590    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0191    2.5955   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4525    1.5420    3.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325    0.2496   -3.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511   -2.6329   -3.2624 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
 18 35  1  0
M  RAD  1  17   2
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₇N₂O₃

Average Molecular Weight

249.2857

Monoisotopic Molecular Weight

249.12391742

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(N[CH]C2(O)CCN=C(C)O)C=C1

InChI Identifier

InChI=1S/C13H17N2O3/c1-9(16)14-6-5-13(17)8-15-12-4-3-10(18-2)7-11(12)13/h3-4,7-8,15,17H,5-6H2,1-2H3,(H,14,16)

InChI Key

SQNQBXWYHXYLQX-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
Benzenoid
Tertiary alcohol
Carboximidic acid
Carboximidic acid derivative
Ether
Secondary amine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0060070)

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	0.68	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.49	ChemAxon
pKa (Strongest Basic)	4.73	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	70.01 m³·mol⁻¹	ChemAxon
Polarizability	26.84 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]+	158.463	31661259
DarkChem	[M-H]-	155.856	31661259
DeepCCS	[M+H]+	160.643	30932474
DeepCCS	[M-H]-	158.285	30932474
DeepCCS	[M-2H]-	191.172	30932474
DeepCCS	[M+Na]+	166.736	30932474
AllCCS	[M+H]+	157.4	32859911
AllCCS	[M+H-H2O]+	153.7	32859911
AllCCS	[M+NH4]+	160.8	32859911
AllCCS	[M+Na]+	161.8	32859911
AllCCS	[M-H]-	161.2	32859911
AllCCS	[M+Na-2H]-	161.4	32859911
AllCCS	[M+HCOO]-	161.7	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melatonin radical,1TMS,isomer #1	COC1=CC=C2N[CH]C(CCN=C(C)O)(O[Si](C)(C)C)C2=C1	2336.9	Semi standard non polar	33892256
Melatonin radical,1TMS,isomer #2	COC1=CC=C2N[CH]C(O)(CCN=C(C)O[Si](C)(C)C)C2=C1	2298.0	Semi standard non polar	33892256
Melatonin radical,1TMS,isomer #3	COC1=CC=C2C(=C1)C(O)(CCN=C(C)O)[CH]N2[Si](C)(C)C	2370.4	Semi standard non polar	33892256
Melatonin radical,2TMS,isomer #1	COC1=CC=C2N[CH]C(CCN=C(C)O[Si](C)(C)C)(O[Si](C)(C)C)C2=C1	2368.7	Semi standard non polar	33892256
Melatonin radical,2TMS,isomer #2	COC1=CC=C2C(=C1)C(CCN=C(C)O)(O[Si](C)(C)C)[CH]N2[Si](C)(C)C	2339.3	Semi standard non polar	33892256
Melatonin radical,2TMS,isomer #3	COC1=CC=C2C(=C1)C(O)(CCN=C(C)O[Si](C)(C)C)[CH]N2[Si](C)(C)C	2313.7	Semi standard non polar	33892256
Melatonin radical,3TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN=C(C)O[Si](C)(C)C)(O[Si](C)(C)C)[CH]N2[Si](C)(C)C	2314.8	Semi standard non polar	33892256
Melatonin radical,3TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN=C(C)O[Si](C)(C)C)(O[Si](C)(C)C)[CH]N2[Si](C)(C)C	2283.3	Standard non polar	33892256
Melatonin radical,3TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN=C(C)O[Si](C)(C)C)(O[Si](C)(C)C)[CH]N2[Si](C)(C)C	2516.6	Standard polar	33892256
Melatonin radical,1TBDMS,isomer #1	COC1=CC=C2N[CH]C(CCN=C(C)O)(O[Si](C)(C)C(C)(C)C)C2=C1	2564.3	Semi standard non polar	33892256
Melatonin radical,1TBDMS,isomer #2	COC1=CC=C2N[CH]C(O)(CCN=C(C)O[Si](C)(C)C(C)(C)C)C2=C1	2540.5	Semi standard non polar	33892256
Melatonin radical,1TBDMS,isomer #3	COC1=CC=C2C(=C1)C(O)(CCN=C(C)O)[CH]N2[Si](C)(C)C(C)(C)C	2602.5	Semi standard non polar	33892256
Melatonin radical,2TBDMS,isomer #1	COC1=CC=C2N[CH]C(CCN=C(C)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C2=C1	2762.9	Semi standard non polar	33892256
Melatonin radical,2TBDMS,isomer #2	COC1=CC=C2C(=C1)C(CCN=C(C)O)(O[Si](C)(C)C(C)(C)C)[CH]N2[Si](C)(C)C(C)(C)C	2814.1	Semi standard non polar	33892256
Melatonin radical,2TBDMS,isomer #3	COC1=CC=C2C(=C1)C(O)(CCN=C(C)O[Si](C)(C)C(C)(C)C)[CH]N2[Si](C)(C)C(C)(C)C	2786.9	Semi standard non polar	33892256
Melatonin radical,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)[CH]N2[Si](C)(C)C(C)(C)C	2984.2	Semi standard non polar	33892256
Melatonin radical,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)[CH]N2[Si](C)(C)C(C)(C)C	2921.0	Standard non polar	33892256
Melatonin radical,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)[CH]N2[Si](C)(C)C(C)(C)C	2824.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Melatonin radical GC-MS (Non-derivatized) - 70eV, Positive	splash10-005a-7930000000-65d79b32ce9587b5110b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melatonin radical GC-MS (2 TMS) - 70eV, Positive	splash10-002r-5239000000-852f515f966b0914f52f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melatonin radical 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 - Melatonin radical 10V, Positive-QTOF	splash10-0a4i-1390000000-c4582be97b1bc11d2bde	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin radical 20V, Positive-QTOF	splash10-0006-1920000000-aae3fdc92b27e244d612	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin radical 40V, Positive-QTOF	splash10-0006-5900000000-c34ed8b526002cbc6912	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin radical 10V, Positive-QTOF	splash10-0006-0960000000-08878042d9f890de2062	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin radical 20V, Positive-QTOF	splash10-03fr-0900000000-4db7088992f76f989e62	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melatonin radical 40V, Positive-QTOF	splash10-05fs-0910000000-162d006c34b66fd06914	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

131769813

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

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Showing metabocard for Melatonin radical (HMDB0060070)

MOL for HMDB0060070 (Melatonin radical)

3D MOL for HMDB0060070 (Melatonin radical)

3D SDF for HMDB0060070 (Melatonin radical)

3D-SDF for HMDB0060070 (Melatonin radical)

PDB for HMDB0060070 (Melatonin radical)

3D PDB for HMDB0060070 (Melatonin radical)

SMILES for HMDB0060070 (Melatonin radical)

INCHI for HMDB0060070 (Melatonin radical)

Structure for HMDB0060070 (Melatonin radical)

3D Structure for HMDB0060070 (Melatonin radical)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra