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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:00:58 UTC

Update Date

2019-07-23 07:15:08 UTC

HMDB ID

HMDB0060811

Secondary Accession Numbers

HMDB60811

Metabolite Identification

Common Name

cyclic Melatonin

Description

cyclic Melatonin belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. cyclic Melatonin is an extremely weak basic (essentially neutral) compound (based on its pKa). Melatonin Listen/ˌmɛləˈtoʊnɪn/, also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring compound found in animals, plants, and microbes. cyclic Melatonin is a metabolite of melatonin. 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.

Structure

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

HMDB0060811
     RDKit          3D
cyclic Melatonin
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.4121    0.5174   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2892   -0.3136   -0.6297 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    0.1148   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7974    1.3767    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    1.7380    0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4317    0.8921    0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8874    0.9968    0.6429 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322   -0.1319    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499   -0.9681   -0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852   -0.3460   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693   -0.7449   -0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -2.2263   -0.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5024   -2.1936    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049   -0.7807    0.1764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535   -0.1097    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    1.3643    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1207   -0.7925    0.0651 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3080    0.0430   -0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5529    0.6993    0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2152    1.4802   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    2.0300    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173    2.7209    1.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3996    1.8309    1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1804   -1.7102   -0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848   -3.0979   -0.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.1899   -1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3212   -2.7786   -0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3205   -2.5706    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9572    1.6477    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3444    1.7869   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1478    1.7153   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 11  3  1  0
 10  6  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
M  END


  Mrv0541 07041312002D          

 17 19  0  0  0  0            999 V2000
    3.2673    0.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4639    0.7806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999    1.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0964    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5324    1.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719    2.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0950    3.0586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5628    2.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924    1.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9502    1.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270    1.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876    2.5443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856    3.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7042    3.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650    3.9622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5753    2.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1393    2.1722    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
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
  3 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060811

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O2/c1-8(16)15-6-5-10-11-7-9(17-2)3-4-12(11)14-13(10)15/h3-4,7,14H,5-6H2,1-2H3

> <INCHI_KEY>
ZQJVLSOGSIIBCF-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O2

> <MOLECULAR_WEIGHT>
230.2625

> <EXACT_MASS>
230.105527702

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.268696802133622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{5-methoxy-1H,2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethan-1-one

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.1452924943333334

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.92382072954248

> <JCHEM_PKA_STRONGEST_BASIC>
-3.897073520964589

> <JCHEM_POLAR_SURFACE_AREA>
45.33

> <JCHEM_REFRACTIVITY>
64.14950000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{5-methoxy-2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060811
     RDKit          3D
cyclic Melatonin
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.4121    0.5174   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2892   -0.3136   -0.6297 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    0.1148   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7974    1.3767    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    1.7380    0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4317    0.8921    0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8874    0.9968    0.6429 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322   -0.1319    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499   -0.9681   -0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852   -0.3460   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693   -0.7449   -0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -2.2263   -0.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5024   -2.1936    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049   -0.7807    0.1764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535   -0.1097    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    1.3643    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1207   -0.7925    0.0651 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3080    0.0430   -0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5529    0.6993    0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2152    1.4802   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    2.0300    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173    2.7209    1.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3996    1.8309    1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1804   -1.7102   -0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848   -3.0979   -0.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.1899   -1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3212   -2.7786   -0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3205   -2.5706    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9572    1.6477    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3444    1.7869   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1478    1.7153   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 11  3  1  0
 10  6  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  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       6.099   1.807   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.599   1.457   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.546   2.581   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.047   2.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.994   3.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.441   4.829   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.177   5.709   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.051   4.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.546   3.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.774   2.395   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.037   3.276   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.590   4.749   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -3.520   5.977   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.048   5.786   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.921   7.396   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.941   5.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.993   4.055   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    6   17                                                       
CONECT   17   16    3                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0060811
HETATM    1  C1  UNL     1       5.412   0.517  -0.443  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.289  -0.314  -0.630  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.021   0.115  -0.273  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.797   1.377   0.282  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.500   1.738   0.615  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.432   0.892   0.414  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.887   0.997   0.643  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.532  -0.132   0.265  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.550  -0.968  -0.221  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.685  -0.346  -0.136  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.969  -0.745  -0.482  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.226  -2.226  -0.650  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.502  -2.194   0.130  1.00  0.00           C  
HETATM   14  N2  UNL     1      -2.805  -0.781   0.176  1.00  0.00           N  
HETATM   15  C12 UNL     1      -4.054  -0.110   0.145  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.149   1.364   0.204  1.00  0.00           C  
HETATM   17  O2  UNL     1      -5.121  -0.793   0.065  1.00  0.00           O  
HETATM   18  H1  UNL     1       6.308   0.043  -0.873  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.553   0.699   0.639  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.215   1.480  -0.956  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.646   2.030   0.434  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.317   2.721   1.049  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.400   1.831   1.061  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.180  -1.710  -0.913  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.585  -3.098  -0.412  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.425  -2.190  -1.745  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.321  -2.779  -0.334  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.320  -2.571   1.171  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.957   1.648   1.274  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.344   1.787  -0.427  1.00  0.00           H  
HETATM   31  H14 UNL     1      -5.148   1.715  -0.068  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   10
CONECT    7    8   23
CONECT    8    9    9   14
CONECT    9   10   12
CONECT   10   11   11
CONECT   11   24
CONECT   12   13   25   26
CONECT   13   14   27   28
CONECT   14   15
CONECT   15   16   17   17
CONECT   16   29   30   31
END

HMDB0060811
     RDKit          3D
cyclic Melatonin
 31 33  0  0  0  0  0  0  0  0999 V2000
    5.4121    0.5174   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2892   -0.3136   -0.6297 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    0.1148   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7974    1.3767    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    1.7380    0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4317    0.8921    0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8874    0.9968    0.6429 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322   -0.1319    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499   -0.9681   -0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852   -0.3460   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693   -0.7449   -0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -2.2263   -0.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5024   -2.1936    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049   -0.7807    0.1764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535   -0.1097    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    1.3643    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1207   -0.7925    0.0651 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3080    0.0430   -0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5529    0.6993    0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2152    1.4802   -0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    2.0300    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173    2.7209    1.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3996    1.8309    1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1804   -1.7102   -0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848   -3.0979   -0.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.1899   -1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3212   -2.7786   -0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3205   -2.5706    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9572    1.6477    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3444    1.7869   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1478    1.7153   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 11  3  1  0
 10  6  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄N₂O₂

Average Molecular Weight

230.2625

Monoisotopic Molecular Weight

230.105527702

IUPAC Name

1-{5-methoxy-1H,2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethan-1-one

Traditional Name

1-{5-methoxy-2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethanone

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1

InChI Identifier

InChI=1S/C13H14N2O2/c1-8(16)15-6-5-10-11-7-9(17-2)3-4-12(11)14-13(10)15/h3-4,7,14H,5-6H2,1-2H3

InChI Key

ZQJVLSOGSIIBCF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
3-alkylindole
Indole
Anisole
Alkyl aryl ether
Benzenoid
Pyrrole
Heteroaromatic compound
Acetamide
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Ether
Azacycle
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060811)
Liver (HMDB: HMDB0060811)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060811)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060811)

Cellular substructure

Cytoplasm (HMDB: HMDB0060811)

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	0.73 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.15	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.92	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.15 m³·mol⁻¹	ChemAxon
Polarizability	25.27 Å³	ChemAxon
Number of Rings	3	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]+	153.961	31661259
DarkChem	[M-H]-	154.364	31661259
DeepCCS	[M+H]+	157.085	30932474
DeepCCS	[M-H]-	154.727	30932474
DeepCCS	[M-2H]-	187.614	30932474
DeepCCS	[M+Na]+	163.179	30932474
AllCCS	[M+H]+	151.7	32859911
AllCCS	[M+H-H2O]+	147.7	32859911
AllCCS	[M+NH4]+	155.4	32859911
AllCCS	[M+Na]+	156.5	32859911
AllCCS	[M-H]-	157.7	32859911
AllCCS	[M+Na-2H]-	157.5	32859911
AllCCS	[M+HCOO]-	157.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cyclic Melatonin	COC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1	3420.5	Standard polar	33892256
cyclic Melatonin	COC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1	2268.5	Standard non polar	33892256
cyclic Melatonin	COC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1	2400.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cyclic Melatonin,1TMS,isomer #1	COC1=CC=C2C(=C1)C1=C(N(C(C)=O)CC1)N2[Si](C)(C)C	2373.0	Semi standard non polar	33892256
cyclic Melatonin,1TMS,isomer #1	COC1=CC=C2C(=C1)C1=C(N(C(C)=O)CC1)N2[Si](C)(C)C	2207.0	Standard non polar	33892256
cyclic Melatonin,1TMS,isomer #1	COC1=CC=C2C(=C1)C1=C(N(C(C)=O)CC1)N2[Si](C)(C)C	2778.1	Standard polar	33892256
cyclic Melatonin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C1=C(N(C(C)=O)CC1)N2[Si](C)(C)C(C)(C)C	2552.9	Semi standard non polar	33892256
cyclic Melatonin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C1=C(N(C(C)=O)CC1)N2[Si](C)(C)C(C)(C)C	2458.2	Standard non polar	33892256
cyclic Melatonin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C1=C(N(C(C)=O)CC1)N2[Si](C)(C)C(C)(C)C	2862.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic Melatonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-2940000000-d53020fefa4b9ff88905	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic Melatonin 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 - cyclic Melatonin 10V, Positive-QTOF	splash10-0019-0960000000-01477cd2a6e830e6c89d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 20V, Positive-QTOF	splash10-000i-0910000000-2cffb22e029f9ef835cf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 40V, Positive-QTOF	splash10-00di-0900000000-725896b4bf698292ad2d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 10V, Negative-QTOF	splash10-004r-0690000000-51fa63eaeeab95106805	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 20V, Negative-QTOF	splash10-0079-0910000000-279fa56711dd704f26d7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 40V, Negative-QTOF	splash10-00di-0900000000-33dc4a10981f0a2e02a4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 10V, Positive-QTOF	splash10-001i-0090000000-40f9b16c23efffb12756	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 20V, Positive-QTOF	splash10-001r-0690000000-9175dbe6bcb254266962	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 40V, Positive-QTOF	splash10-052r-0900000000-1617ad62aaf63c0fc662	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 10V, Negative-QTOF	splash10-004i-0190000000-5a64252203fed142078c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 20V, Negative-QTOF	splash10-0079-0920000000-668b2e1438793f1bde9a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic Melatonin 40V, Negative-QTOF	splash10-00di-0920000000-497a26e697fdbad2d616	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

129373222

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 cyclic Melatonin (HMDB0060811)

MOL for HMDB0060811 (cyclic Melatonin)

3D MOL for HMDB0060811 (cyclic Melatonin)

3D SDF for HMDB0060811 (cyclic Melatonin)

3D-SDF for HMDB0060811 (cyclic Melatonin)

PDB for HMDB0060811 (cyclic Melatonin)

3D PDB for HMDB0060811 (cyclic Melatonin)

SMILES for HMDB0060811 (cyclic Melatonin)

INCHI for HMDB0060811 (cyclic Melatonin)

Structure for HMDB0060811 (cyclic Melatonin)

3D Structure for HMDB0060811 (cyclic Melatonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra