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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:55:01 UTC

Update Date

2021-09-14 14:57:31 UTC

HMDB ID

HMDB0060721

Secondary Accession Numbers

HMDB60721

Metabolite Identification

Common Name

2-Oxomelatonin

Description

2-Oxomelatonin 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. 2-Oxomelatonin is an extremely weak basic (essentially neutral) compound (based on its pKa). 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. 2-Oxomelatonin is a metabolite of melatonin.

Structure

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

HMDB0060721
     RDKit          3D
2-Oxomelatonin
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.4142    0.0941    2.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1937    0.5947    1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6618    0.3396    0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -0.4648   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7316   -0.6821   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -0.1027   -1.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8240    0.7025   -0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4499    0.9056    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4168    1.1528   -1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    0.8853   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8539   -0.5714   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0521   -0.7105    0.3374 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2298   -0.1314    1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4919   -0.3176    2.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3283    0.5570    2.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.5588   -2.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167    0.6485   -3.8193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377   -0.2090   -3.0498 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2256    0.1465    1.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2935   -0.9690    2.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7065    0.7186    3.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2737   -0.9314   -0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -1.3117   -2.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9063    1.5421    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535    2.2681   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.4795    0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5151    1.2444   -1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0276   -0.9916    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -1.1618   -1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8588   -1.2817   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3882   -0.1552    1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5606    0.3771    3.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089   -1.3504    2.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0347   -0.7744   -3.8945 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  9 16  1  0
 16 17  2  0
 16 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
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 18 34  1  0
M  END


  Mrv0541 07041311552D          

 18 19  0  0  0  0            999 V2000
   -6.2785    4.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4716    3.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2166    3.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4097    2.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547    2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2942    0.8266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873    0.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8742    0.4461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4010    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6866    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9721    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    2.2311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432    0.9936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5137    1.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7687    2.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
  3 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060721

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC(=O)C2CCNC(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O3/c1-8(16)14-6-5-10-11-7-9(18-2)3-4-12(11)15-13(10)17/h3-4,7,10H,5-6H2,1-2H3,(H,14,16)(H,15,17)

> <INCHI_KEY>
HNEAVHQAQROOMN-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O3

> <MOLECULAR_WEIGHT>
248.2777

> <EXACT_MASS>
248.116092388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.454702266754737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.17722005433333338

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.050652940763086

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.226972490017225

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6287485042949242

> <JCHEM_POLAR_SURFACE_AREA>
67.43

> <JCHEM_REFRACTIVITY>
68.2536

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[2-(5-methoxy-2-oxo-1,3-dihydroindol-3-yl)ethyl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060721
     RDKit          3D
2-Oxomelatonin
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.4142    0.0941    2.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1937    0.5947    1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6618    0.3396    0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -0.4648   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7316   -0.6821   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -0.1027   -1.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8240    0.7025   -0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4499    0.9056    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4168    1.1528   -1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    0.8853   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8539   -0.5714   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0521   -0.7105    0.3374 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2298   -0.1314    1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4919   -0.3176    2.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3283    0.5570    2.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.5588   -2.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167    0.6485   -3.8193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377   -0.2090   -3.0498 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2256    0.1465    1.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2935   -0.9690    2.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7065    0.7186    3.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2737   -0.9314   -0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -1.3117   -2.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9063    1.5421    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535    2.2681   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.4795    0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5151    1.2444   -1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0276   -0.9916    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -1.1618   -1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8588   -1.2817   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3882   -0.1552    1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5606    0.3771    3.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089   -1.3504    2.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0347   -0.7744   -3.8945 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  9 16  1  0
 16 17  2  0
 16 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
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 18 34  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     -11.720   7.591   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -10.214   7.270   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -9.738   5.806   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.231   5.486   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.755   4.021   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.786   2.877   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -8.016   1.543   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -6.510   1.863   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.365   0.833   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.349   3.395   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.015   4.165   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.681   3.395   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -2.348   4.165   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.014   3.395   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.320   4.165   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.014   1.855   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -10.292   3.197   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.768   4.661   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    6   18                                                       
CONECT   18   17    3                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0060721
HETATM    1  C1  UNL     1      -4.414   0.094   2.309  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.194   0.595   1.833  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.662   0.340   0.600  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.321  -0.465  -0.300  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.732  -0.682  -1.524  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.495  -0.103  -1.851  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.824   0.702  -0.965  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.450   0.906   0.276  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.417   1.153  -1.577  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.641   0.885  -0.746  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.854  -0.571  -0.461  1.00  0.00           C  
HETATM   12  N1  UNL     1       3.052  -0.710   0.337  1.00  0.00           N  
HETATM   13  C11 UNL     1       3.230  -0.131   1.613  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.492  -0.318   2.373  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.328   0.557   2.143  1.00  0.00           O  
HETATM   16  C13 UNL     1       0.446   0.559  -2.900  1.00  0.00           C  
HETATM   17  O3  UNL     1       1.317   0.649  -3.819  1.00  0.00           O  
HETATM   18  N2  UNL     1      -0.738  -0.209  -3.050  1.00  0.00           N  
HETATM   19  H1  UNL     1      -5.226   0.147   1.556  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.294  -0.969   2.574  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.706   0.719   3.180  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.274  -0.931  -0.092  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.248  -1.312  -2.228  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.906   1.542   0.959  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.353   2.268  -1.668  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.549   1.480   0.167  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.515   1.244  -1.320  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.028  -0.992   0.179  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.978  -1.162  -1.371  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.859  -1.282  -0.048  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.388  -0.155   1.708  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.561   0.377   3.221  1.00  0.00           H  
HETATM   33  H15 UNL     1       4.509  -1.350   2.785  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.035  -0.774  -3.894  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   16   25
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   30
CONECT   13   14   15   15
CONECT   14   31   32   33
CONECT   16   17   17   18
CONECT   18   34
END

HMDB0060721
     RDKit          3D
2-Oxomelatonin
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.4142    0.0941    2.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1937    0.5947    1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6618    0.3396    0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -0.4648   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7316   -0.6821   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -0.1027   -1.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8240    0.7025   -0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4499    0.9056    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4168    1.1528   -1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    0.8853   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8539   -0.5714   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0521   -0.7105    0.3374 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2298   -0.1314    1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4919   -0.3176    2.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3283    0.5570    2.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.5588   -2.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167    0.6485   -3.8193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377   -0.2090   -3.0498 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2256    0.1465    1.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2935   -0.9690    2.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7065    0.7186    3.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2737   -0.9314   -0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -1.3117   -2.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9063    1.5421    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535    2.2681   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.4795    0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5151    1.2444   -1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0276   -0.9916    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -1.1618   -1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8588   -1.2817   -0.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3882   -0.1552    1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5606    0.3771    3.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089   -1.3504    2.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0347   -0.7744   -3.8945 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  9 16  1  0
 16 17  2  0
 16 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
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₆N₂O₃

Average Molecular Weight

248.2777

Monoisotopic Molecular Weight

248.116092388

IUPAC Name

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

Traditional Name

N-[2-(5-methoxy-2-oxo-1,3-dihydroindol-3-yl)ethyl]acetamide

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(NC(=O)C2CCNC(C)=O)C=C1

InChI Identifier

InChI=1S/C13H16N2O3/c1-8(16)14-6-5-10-11-7-9(18-2)3-4-12(11)15-13(10)17/h3-4,7,10H,5-6H2,1-2H3,(H,14,16)(H,15,17)

InChI Key

HNEAVHQAQROOMN-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
Benzenoid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carboxylic acid derivative
Ether
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060721)
Liver (HMDB: HMDB0060721)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060721)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060721)

Cellular substructure

Cytoplasm (HMDB: HMDB0060721)

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	0.51 g/L	ALOGPS
logP	0.84	ALOGPS
logP	0.18	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.23	ChemAxon
pKa (Strongest Basic)	-0.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.25 m³·mol⁻¹	ChemAxon
Polarizability	26.45 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]+	156.48	31661259
DarkChem	[M-H]-	158.266	31661259
DeepCCS	[M+H]+	160.503	30932474
DeepCCS	[M-H]-	158.145	30932474
DeepCCS	[M-2H]-	191.032	30932474
DeepCCS	[M+Na]+	166.597	30932474
AllCCS	[M+H]+	156.4	32859911
AllCCS	[M+H-H2O]+	152.7	32859911
AllCCS	[M+NH4]+	159.8	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	160.6	32859911
AllCCS	[M+Na-2H]-	160.7	32859911
AllCCS	[M+HCOO]-	160.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Oxomelatonin	COC1=CC2=C(NC(=O)C2CCNC(C)=O)C=C1	3530.7	Standard polar	33892256
2-Oxomelatonin	COC1=CC2=C(NC(=O)C2CCNC(C)=O)C=C1	2465.0	Standard non polar	33892256
2-Oxomelatonin	COC1=CC2=C(NC(=O)C2CCNC(C)=O)C=C1	2541.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Oxomelatonin,1TMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)C(=O)N2[Si](C)(C)C	2450.8	Semi standard non polar	33892256
2-Oxomelatonin,1TMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)C(=O)N2[Si](C)(C)C	2295.8	Standard non polar	33892256
2-Oxomelatonin,1TMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)C(=O)N2[Si](C)(C)C	3065.0	Standard polar	33892256
2-Oxomelatonin,1TMS,isomer #2	COC1=CC=C2NC(=O)C(CCN(C(C)=O)[Si](C)(C)C)C2=C1	2513.8	Semi standard non polar	33892256
2-Oxomelatonin,1TMS,isomer #2	COC1=CC=C2NC(=O)C(CCN(C(C)=O)[Si](C)(C)C)C2=C1	2505.0	Standard non polar	33892256
2-Oxomelatonin,1TMS,isomer #2	COC1=CC=C2NC(=O)C(CCN(C(C)=O)[Si](C)(C)C)C2=C1	3552.9	Standard polar	33892256
2-Oxomelatonin,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C)C(=O)N2[Si](C)(C)C	2355.6	Semi standard non polar	33892256
2-Oxomelatonin,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C)C(=O)N2[Si](C)(C)C	2463.0	Standard non polar	33892256
2-Oxomelatonin,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C)C(=O)N2[Si](C)(C)C	2808.8	Standard polar	33892256
2-Oxomelatonin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)C(=O)N2[Si](C)(C)C(C)(C)C	2708.5	Semi standard non polar	33892256
2-Oxomelatonin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)C(=O)N2[Si](C)(C)C(C)(C)C	2540.6	Standard non polar	33892256
2-Oxomelatonin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCNC(C)=O)C(=O)N2[Si](C)(C)C(C)(C)C	3123.4	Standard polar	33892256
2-Oxomelatonin,1TBDMS,isomer #2	COC1=CC=C2NC(=O)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1	2719.7	Semi standard non polar	33892256
2-Oxomelatonin,1TBDMS,isomer #2	COC1=CC=C2NC(=O)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1	2709.2	Standard non polar	33892256
2-Oxomelatonin,1TBDMS,isomer #2	COC1=CC=C2NC(=O)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C2=C1	3554.5	Standard polar	33892256
2-Oxomelatonin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2861.2	Semi standard non polar	33892256
2-Oxomelatonin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2893.2	Standard non polar	33892256
2-Oxomelatonin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2966.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Oxomelatonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-007o-8690000000-ac00e2a537a1b47e88c1	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Oxomelatonin 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 - 2-Oxomelatonin 10V, Positive-QTOF	splash10-052b-0190000000-9fc6bef12622598cadca	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 20V, Positive-QTOF	splash10-052f-2950000000-f23c337d65c6cbcc293d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 40V, Positive-QTOF	splash10-0006-5900000000-d545a54d055f47b195af	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 10V, Negative-QTOF	splash10-052b-0090000000-46a4f57c62ffbeae698c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 20V, Negative-QTOF	splash10-0a4j-5490000000-edea543cda37383839c9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 40V, Negative-QTOF	splash10-052f-9100000000-861766023c6d98ff5858	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 10V, Positive-QTOF	splash10-0006-0940000000-9dd4439bce43b00ef69b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 20V, Positive-QTOF	splash10-0006-0910000000-cb02409cea899bbc7228	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 40V, Positive-QTOF	splash10-08ml-0900000000-00c1ae125439b529c9c9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 10V, Negative-QTOF	splash10-002b-0590000000-ce88a04ecb2082bb7e75	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 20V, Negative-QTOF	splash10-0bt9-9510000000-c39e708a8f2ad64eed9d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxomelatonin 40V, Negative-QTOF	splash10-0006-9410000000-3897ee7ca09ac779b362	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

9859734

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 2-Oxomelatonin (HMDB0060721)

MOL for HMDB0060721 (2-Oxomelatonin)

3D MOL for HMDB0060721 (2-Oxomelatonin)

3D SDF for HMDB0060721 (2-Oxomelatonin)

3D-SDF for HMDB0060721 (2-Oxomelatonin)

PDB for HMDB0060721 (2-Oxomelatonin)

3D PDB for HMDB0060721 (2-Oxomelatonin)

SMILES for HMDB0060721 (2-Oxomelatonin)

INCHI for HMDB0060721 (2-Oxomelatonin)

Structure for HMDB0060721 (2-Oxomelatonin)

3D Structure for HMDB0060721 (2-Oxomelatonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra