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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:42:30 UTC

Update Date

2021-09-26 23:08:23 UTC

HMDB ID

HMDB0254414

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Meisoindigo

Description

2'-hydroxy-1'-methyl-1'H,2H-[3,3'-biindole]-2-one belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position. Based on a literature review very few articles have been published on 2'-hydroxy-1'-methyl-1'H,2H-[3,3'-biindole]-2-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Meisoindigo is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Meisoindigo is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254414
     RDKit          3D
Meisoindigo
 33 36  0  0  0  0  0  0  0  0999 V2000
   -2.3515    2.8092    0.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764    1.5698    0.3239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672    1.4503   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4137    2.4360   -0.4174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517    0.1309   -0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507   -0.4347   -1.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0716   -0.3770   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    0.1920    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518    0.1205    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7936   -0.5047    0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3056   -1.0609   -1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742   -1.0064   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3653   -1.4814   -2.5146 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783   -1.1551   -2.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0302   -1.4105   -3.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038   -0.5461   -0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8821   -1.8559   -0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1513   -2.2177    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0164   -1.2979    0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290    0.0131    0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696    0.3804    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0332    3.6099    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227    3.0106    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4539    2.7251    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    2.3756   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028    0.6908    1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547    0.5889    1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8362   -0.5436    0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411   -1.5556   -1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2009   -2.5845   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4813   -3.2423    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0123   -1.5728    1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3091    0.7439    1.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 14  6  1  0
 21 16  1  0
 12  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END


  Mrv1652309112115432D          

 21 24  0  0  0  0            999 V2000
   -0.5683    2.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    1.8341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2193    2.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0398    2.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5247    2.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    1.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687    1.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683    0.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254414

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(O)=C(C2=CC=CC=C12)C1=C2C=CC=CC2=NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H12N2O2/c1-19-13-9-5-3-7-11(13)15(17(19)21)14-10-6-2-4-8-12(10)18-16(14)20/h2-9,21H,1H3

> <INCHI_KEY>
XZYXCQXTKOYHGK-UHFFFAOYSA-N

> <FORMULA>
C17H12N2O2

> <MOLECULAR_WEIGHT>
276.295

> <EXACT_MASS>
276.089877634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.294966952362962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2'-hydroxy-1'-methyl-1'H,2H-[3,3'-biindole]-2-one

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
2.5503058746666665

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.901136777269137

> <JCHEM_PKA_STRONGEST_BASIC>
0.22273150675198117

> <JCHEM_POLAR_SURFACE_AREA>
54.589999999999996

> <JCHEM_REFRACTIVITY>
82.59959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2'-hydroxy-1'-methyl-[3,3'-biindole]-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254414
     RDKit          3D
Meisoindigo
 33 36  0  0  0  0  0  0  0  0999 V2000
   -2.3515    2.8092    0.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764    1.5698    0.3239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672    1.4503   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4137    2.4360   -0.4174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517    0.1309   -0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507   -0.4347   -1.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0716   -0.3770   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    0.1920    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518    0.1205    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7936   -0.5047    0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3056   -1.0609   -1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742   -1.0064   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3653   -1.4814   -2.5146 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783   -1.1551   -2.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0302   -1.4105   -3.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038   -0.5461   -0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8821   -1.8559   -0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1513   -2.2177    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0164   -1.2979    0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290    0.0131    0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696    0.3804    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0332    3.6099    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227    3.0106    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4539    2.7251    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    2.3756   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028    0.6908    1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547    0.5889    1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8362   -0.5436    0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411   -1.5556   -1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2009   -2.5845   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4813   -3.2423    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0123   -1.5728    1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3091    0.7439    1.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 14  6  1  0
 21 16  1  0
 12  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -1.061   4.329   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.185   3.424   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.650   3.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.276   5.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.808   5.467   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.713   4.221   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.086   2.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.555   2.654   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.185   1.884   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.061   0.978   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   20                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   12   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0254414
HETATM    1  C1  UNL     1      -2.351   2.809   0.800  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.776   1.570   0.324  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.567   1.450  -0.200  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.414   2.436  -0.417  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.352   0.131  -0.543  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.851  -0.435  -1.150  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.072  -0.377  -0.631  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.516   0.192   0.541  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.852   0.120   0.867  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.794  -0.505   0.064  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.306  -1.061  -1.100  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.974  -1.006  -1.455  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.365  -1.481  -2.515  1.00  0.00           N  
HETATM   14  C11 UNL     1       0.978  -1.155  -2.400  1.00  0.00           C  
HETATM   15  O2  UNL     1       0.030  -1.411  -3.181  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.504  -0.546  -0.195  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.882  -1.856  -0.290  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.151  -2.218   0.166  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.016  -1.298   0.702  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.629   0.013   0.793  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.370   0.380   0.341  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.033   3.610   0.090  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.923   3.011   1.812  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.454   2.725   0.857  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.026   2.376  -1.218  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.803   0.691   1.195  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.155   0.589   1.811  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.836  -0.544   0.349  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.041  -1.556  -1.739  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.201  -2.584  -0.712  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.481  -3.242   0.106  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.012  -1.573   1.062  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.309   0.744   1.215  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21
CONECT    3    4    5    5
CONECT    4   25
CONECT    5    6   16
CONECT    6    7    7   14
CONECT    7    8   12
CONECT    8    9    9   26
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   29
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   15
CONECT   16   17   17   21
CONECT   17   18   30
CONECT   18   19   19   31
CONECT   19   20   32
CONECT   20   21   21   33
END

HMDB0254414
     RDKit          3D
Meisoindigo
 33 36  0  0  0  0  0  0  0  0999 V2000
   -2.3515    2.8092    0.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764    1.5698    0.3239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672    1.4503   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4137    2.4360   -0.4174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517    0.1309   -0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507   -0.4347   -1.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0716   -0.3770   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    0.1920    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518    0.1205    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7936   -0.5047    0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3056   -1.0609   -1.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742   -1.0064   -1.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3653   -1.4814   -2.5146 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783   -1.1551   -2.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0302   -1.4105   -3.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038   -0.5461   -0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8821   -1.8559   -0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1513   -2.2177    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0164   -1.2979    0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290    0.0131    0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696    0.3804    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0332    3.6099    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227    3.0106    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4539    2.7251    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    2.3756   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028    0.6908    1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547    0.5889    1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8362   -0.5436    0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411   -1.5556   -1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2009   -2.5845   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4813   -3.2423    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0123   -1.5728    1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3091    0.7439    1.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 14  6  1  0
 21 16  1  0
 12  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Methylisoindigotin	MeSH
Dian III	MeSH

Chemical Formula

C₁₇H₁₂N₂O₂

Average Molecular Weight

276.295

Monoisotopic Molecular Weight

276.089877634

IUPAC Name

2'-hydroxy-1'-methyl-1'H,2H-[3,3'-biindole]-2-one

Traditional Name

2'-hydroxy-1'-methyl-[3,3'-biindole]-2-one

CAS Registry Number

Not Available

SMILES

CN1C(O)=C(C2=CC=CC=C12)C1=C2C=CC=CC2=NC1=O

InChI Identifier

InChI=1S/C17H12N2O2/c1-19-13-9-5-3-7-11(13)15(17(19)21)14-10-6-2-4-8-12(10)18-16(14)20/h2-9,21H,1H3

InChI Key

XZYXCQXTKOYHGK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

N-alkylindoles

Direct Parent

N-alkylindoles

Alternative Parents

Substituents

N-alkylindole
Hydroxyindole
Indole
Benzenoid
Substituted pyrrole
N-methylpyrrole
Heteroaromatic compound
Pyrrole
N-acylimine
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	3.25	ALOGPS
logP	2.55	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.9	ChemAxon
pKa (Strongest Basic)	0.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.6 m³·mol⁻¹	ChemAxon
Polarizability	29.29 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M-2H]-	194.881	30932474
DeepCCS	[M+Na]+	170.371	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Meisoindigo	CN1C(O)=C(C2=CC=CC=C12)C1=C2C=CC=CC2=NC1=O	3934.2	Standard polar	33892256
Meisoindigo	CN1C(O)=C(C2=CC=CC=C12)C1=C2C=CC=CC2=NC1=O	2863.2	Standard non polar	33892256
Meisoindigo	CN1C(O)=C(C2=CC=CC=C12)C1=C2C=CC=CC2=NC1=O	2973.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Meisoindigo GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0190000000-fbe31273b97399c27d44	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Meisoindigo GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Meisoindigo GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Meisoindigo GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Meisoindigo 10V, Positive-QTOF	splash10-004i-0090000000-68b7aa4329714f5bebd8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meisoindigo 20V, Positive-QTOF	splash10-004i-0090000000-e994bb3162b62e336b79	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meisoindigo 40V, Positive-QTOF	splash10-0002-0290000000-6d8a38c19feeef43687e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meisoindigo 10V, Negative-QTOF	splash10-004i-0090000000-5a203c74061ba5d5bfc1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meisoindigo 20V, Negative-QTOF	splash10-004i-0090000000-5a203c74061ba5d5bfc1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meisoindigo 40V, Negative-QTOF	splash10-00dj-0090000000-4fa160f6c0e0b8c13d3b	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

126274

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Meisoindigo (HMDB0254414)

MOL for HMDB0254414 (Meisoindigo)

3D MOL for HMDB0254414 (Meisoindigo)

3D SDF for HMDB0254414 (Meisoindigo)

3D-SDF for HMDB0254414 (Meisoindigo)

PDB for HMDB0254414 (Meisoindigo)

3D PDB for HMDB0254414 (Meisoindigo)

SMILES for HMDB0254414 (Meisoindigo)

INCHI for HMDB0254414 (Meisoindigo)

Structure for HMDB0254414 (Meisoindigo)

3D Structure for HMDB0254414 (Meisoindigo)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra