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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:00:55 UTC

Update Date

2019-07-23 07:15:08 UTC

HMDB ID

HMDB0060810

Secondary Accession Numbers

HMDB60810

Metabolite Identification

Common Name

cyclic 6-Hydroxymelatonin

Description

cyclic 6-Hydroxymelatonin 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 6-Hydroxymelatonin 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. 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. cyclic 6-Hydroxymelatonin is a metabolite of melatonin.

Structure

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

HMDB0060810
     RDKit          3D
cyclic 6-Hydroxymelatonin
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.8680   -0.5378   -0.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701    0.7318   -0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024    0.9648   -0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -0.0451   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660    0.1949   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239   -0.6034    0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241    0.2089    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.4372   -0.2499 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3387    1.4659   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2208    2.4792   -0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784    2.2364   -0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4668    3.2623   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6159   -0.5015    0.3989 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9460   -0.0931    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0982   -0.9422    0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1488    0.9871   -0.5596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263   -1.7075    1.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -1.9711    0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9686   -0.5415   -0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7456   -0.7774    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -1.3573   -0.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -1.0506    0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6074    2.2569   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    3.4761   -0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617    3.0797   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9481   -2.0057    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3496   -0.8936    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0053   -0.6090   -0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3251   -1.6250    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8844   -2.5527    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795   -2.6805   -0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -2.2865    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17 18  1  0
 11  3  1  0
  9  5  2  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  8 23  1  0
 10 24  1  0
 12 25  1  0
 15 26  1  0
 15 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
M  END


  Mrv0541 07041312002D          

 18 20  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
    2.9427    2.3596    0.0000 O   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
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060810

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O3/c1-7(16)15-4-3-8-9-5-12(18-2)11(17)6-10(9)14-13(8)15/h5-6,14,17H,3-4H2,1-2H3

> <INCHI_KEY>
FQZIOEARFRBPDV-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O3

> <MOLECULAR_WEIGHT>
246.2619

> <EXACT_MASS>
246.100442324

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.212368359521992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{6-hydroxy-5-methoxy-1H,2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethan-1-one

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
0.8417271726666671

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.86673209524022

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.286647590802943

> <JCHEM_PKA_STRONGEST_BASIC>
-3.903944392051787

> <JCHEM_POLAR_SURFACE_AREA>
65.56

> <JCHEM_REFRACTIVITY>
66.13040000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{6-hydroxy-5-methoxy-2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060810
     RDKit          3D
cyclic 6-Hydroxymelatonin
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.8680   -0.5378   -0.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701    0.7318   -0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024    0.9648   -0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -0.0451   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660    0.1949   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239   -0.6034    0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241    0.2089    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.4372   -0.2499 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3387    1.4659   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2208    2.4792   -0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784    2.2364   -0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4668    3.2623   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6159   -0.5015    0.3989 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9460   -0.0931    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0982   -0.9422    0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1488    0.9871   -0.5596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263   -1.7075    1.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -1.9711    0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9686   -0.5415   -0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7456   -0.7774    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -1.3573   -0.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -1.0506    0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6074    2.2569   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    3.4761   -0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617    3.0797   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9481   -2.0057    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3496   -0.8936    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0053   -0.6090   -0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3251   -1.6250    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8844   -2.5527    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795   -2.6805   -0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -2.2865    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17 18  1  0
 11  3  1  0
  9  5  2  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  8 23  1  0
 10 24  1  0
 12 25  1  0
 15 26  1  0
 15 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  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
HETATM   18  O   UNK     0       5.493   4.405   0.000  0.00  0.00           O+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   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0060810
HETATM    1  C1  UNL     1       4.868  -0.538  -0.094  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.370   0.732  -0.414  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.002   0.965  -0.387  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.126  -0.045  -0.047  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.766   0.195  -0.023  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.324  -0.603   0.273  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.424   0.209   0.121  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.002   1.437  -0.250  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.339   1.466  -0.348  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.221   2.479  -0.690  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.578   2.236  -0.713  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.467   3.262  -1.059  1.00  0.00           O  
HETATM   13  N2  UNL     1      -2.616  -0.502   0.399  1.00  0.00           N  
HETATM   14  C10 UNL     1      -3.946  -0.093   0.051  1.00  0.00           C  
HETATM   15  C11 UNL     1      -5.098  -0.942   0.409  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.149   0.987  -0.560  1.00  0.00           O  
HETATM   17  C12 UNL     1      -2.226  -1.707   1.096  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.785  -1.971   0.685  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.969  -0.541  -0.276  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.746  -0.777   0.986  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.374  -1.357  -0.683  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.461  -1.051   0.211  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.607   2.257  -0.438  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.880   3.476  -0.945  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.462   3.080  -1.075  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.948  -2.006   0.155  1.00  0.00           H  
HETATM   27  H9  UNL     1      -5.350  -0.894   1.498  1.00  0.00           H  
HETATM   28  H10 UNL     1      -6.005  -0.609  -0.129  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.325  -1.625   2.196  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.884  -2.553   0.749  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.780  -2.680  -0.152  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.158  -2.286   1.537  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   22
CONECT    5    6    9    9
CONECT    6    7    7   18
CONECT    7    8   13
CONECT    8    9   23
CONECT    9   10
CONECT   10   11   11   24
CONECT   11   12
CONECT   12   25
CONECT   13   14   17
CONECT   14   15   16   16
CONECT   15   26   27   28
CONECT   17   18   29   30
CONECT   18   31   32
END

HMDB0060810
     RDKit          3D
cyclic 6-Hydroxymelatonin
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.8680   -0.5378   -0.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701    0.7318   -0.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024    0.9648   -0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -0.0451   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660    0.1949   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239   -0.6034    0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241    0.2089    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.4372   -0.2499 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3387    1.4659   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2208    2.4792   -0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784    2.2364   -0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4668    3.2623   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6159   -0.5015    0.3989 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9460   -0.0931    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0982   -0.9422    0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1488    0.9871   -0.5596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263   -1.7075    1.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -1.9711    0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9686   -0.5415   -0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7456   -0.7774    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -1.3573   -0.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -1.0506    0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6074    2.2569   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    3.4761   -0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617    3.0797   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9481   -2.0057    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3496   -0.8936    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0053   -0.6090   -0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3251   -1.6250    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8844   -2.5527    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795   -2.6805   -0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -2.2865    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17 18  1  0
 11  3  1  0
  9  5  2  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  8 23  1  0
 10 24  1  0
 12 25  1  0
 15 26  1  0
 15 27  1  0
 15 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄N₂O₃

Average Molecular Weight

246.2619

Monoisotopic Molecular Weight

246.100442324

IUPAC Name

1-{6-hydroxy-5-methoxy-1H,2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethan-1-one

Traditional Name

1-{6-hydroxy-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=C1O

InChI Identifier

InChI=1S/C13H14N2O3/c1-7(16)15-4-3-8-9-5-12(18-2)11(17)6-10(9)14-13(8)15/h5-6,14,17H,3-4H2,1-2H3

InChI Key

FQZIOEARFRBPDV-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
Hydroxyindole
3-alkylindole
Indole
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
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: HMDB0060810)
Liver (HMDB: HMDB0060810)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060810)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060810)

Cellular substructure

Cytoplasm (HMDB: HMDB0060810)

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	1.75 g/L	ALOGPS
logP	1.27	ALOGPS
logP	0.84	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.13 m³·mol⁻¹	ChemAxon
Polarizability	26.21 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]+	157.675	31661259
DarkChem	[M-H]-	158.089	31661259
DeepCCS	[M+H]+	156.474	30932474
DeepCCS	[M-H]-	154.116	30932474
DeepCCS	[M-2H]-	187.243	30932474
DeepCCS	[M+Na]+	162.568	30932474
AllCCS	[M+H]+	155.3	32859911
AllCCS	[M+H-H2O]+	151.5	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	160.2	32859911
AllCCS	[M+Na-2H]-	159.9	32859911
AllCCS	[M+HCOO]-	159.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cyclic 6-Hydroxymelatonin	COC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1O	3749.2	Standard polar	33892256
cyclic 6-Hydroxymelatonin	COC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1O	2500.1	Standard non polar	33892256
cyclic 6-Hydroxymelatonin	COC1=CC2=C(NC3=C2CCN3C(C)=O)C=C1O	2618.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cyclic 6-Hydroxymelatonin,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C1=C2CCN1C(C)=O	2535.2	Semi standard non polar	33892256
cyclic 6-Hydroxymelatonin,1TMS,isomer #2	COC1=CC2=C(C=C1O)N([Si](C)(C)C)C1=C2CCN1C(C)=O	2536.1	Semi standard non polar	33892256
cyclic 6-Hydroxymelatonin,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C1=C2CCN1C(C)=O	2562.4	Semi standard non polar	33892256
cyclic 6-Hydroxymelatonin,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C1=C2CCN1C(C)=O	2408.9	Standard non polar	33892256
cyclic 6-Hydroxymelatonin,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C1=C2CCN1C(C)=O	2827.3	Standard polar	33892256
cyclic 6-Hydroxymelatonin,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C1=C2CCN1C(C)=O	2723.1	Semi standard non polar	33892256
cyclic 6-Hydroxymelatonin,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C1=C2CCN1C(C)=O	2740.7	Semi standard non polar	33892256
cyclic 6-Hydroxymelatonin,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=C2CCN1C(C)=O	2905.7	Semi standard non polar	33892256
cyclic 6-Hydroxymelatonin,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=C2CCN1C(C)=O	2903.6	Standard non polar	33892256
cyclic 6-Hydroxymelatonin,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=C2CCN1C(C)=O	3000.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic 6-Hydroxymelatonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uec-2490000000-c8f196c332bb71882b9d	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic 6-Hydroxymelatonin GC-MS (1 TMS) - 70eV, Positive	splash10-0hbd-3093000000-dce525816badc4bb1099	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cyclic 6-Hydroxymelatonin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 10V, Positive-QTOF	splash10-0a4j-0090000000-a99ed1e16994593a509f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 20V, Positive-QTOF	splash10-0a4i-0390000000-bdcb012d7fe85e0008b5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 40V, Positive-QTOF	splash10-000i-0910000000-fed695acf0406f49ad1e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 10V, Negative-QTOF	splash10-0f6t-0090000000-167e69a93cce328c4301	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 20V, Negative-QTOF	splash10-0udr-0690000000-35d419421af3b77d21da	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 40V, Negative-QTOF	splash10-000i-0910000000-d5b76152c6440c325b90	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 10V, Negative-QTOF	splash10-0002-0090000000-b8d979fd88dcbd85fb57	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 20V, Negative-QTOF	splash10-0udr-0690000000-9873a1ba742bddd34835	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 40V, Negative-QTOF	splash10-0f79-0940000000-a1bbdda6f249aff64fa6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 10V, Positive-QTOF	splash10-0002-0090000000-4b96f2fb9c6435e34917	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 20V, Positive-QTOF	splash10-0002-0090000000-534cf3a7b9c5f3d9025e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cyclic 6-Hydroxymelatonin 40V, Positive-QTOF	splash10-0uki-0930000000-fc7ca114e910a1f78f27	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

131769959

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 6-Hydroxymelatonin (HMDB0060810)

MOL for HMDB0060810 (cyclic 6-Hydroxymelatonin)

3D MOL for HMDB0060810 (cyclic 6-Hydroxymelatonin)

3D SDF for HMDB0060810 (cyclic 6-Hydroxymelatonin)

3D-SDF for HMDB0060810 (cyclic 6-Hydroxymelatonin)

PDB for HMDB0060810 (cyclic 6-Hydroxymelatonin)

3D PDB for HMDB0060810 (cyclic 6-Hydroxymelatonin)

SMILES for HMDB0060810 (cyclic 6-Hydroxymelatonin)

INCHI for HMDB0060810 (cyclic 6-Hydroxymelatonin)

Structure for HMDB0060810 (cyclic 6-Hydroxymelatonin)

3D Structure for HMDB0060810 (cyclic 6-Hydroxymelatonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra