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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:47:20 UTC

Update Date

2021-09-26 22:50:38 UTC

HMDB ID

HMDB0243538

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Eseroline

Description

(+)-Eseroline 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. Based on a literature review a significant number of articles have been published on (+)-Eseroline. This compound has been identified in human blood as reported by (PMID: 31557052 ). (+)-eseroline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (+)-Eseroline 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

HMDB0251948
     RDKit          3D
Eseroline
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.7800   -0.6552    1.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6967    0.1509    0.8939 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.5441    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6967    2.0773    0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342    0.9453   -0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    1.3867   -2.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713    0.3949   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849    1.0231   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678    0.2667    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6110    0.8611    0.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2361   -1.1097    0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0274   -1.7322    0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -0.9660   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.3828   -0.3525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8584   -2.7416   -0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938   -0.2058   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4456   -1.1725    2.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1678   -1.3686    0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    0.0210    1.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3642    2.0484    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7501    1.6479   -0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359    2.1235    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7734    3.0300   -0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553    2.4351   -2.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7999    1.4389   -2.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    0.6659   -2.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4273    2.0938   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8076    1.1966    1.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0789   -1.7065    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9604   -2.7995    0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730   -2.8198   -1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2861   -3.0886    0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376   -3.3686   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820   -0.2337   -1.1778 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16  2  1  0
 16  5  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
M  END


  Mrv1652309102122472D          

 16 18  0  0  0  0            999 V2000
    2.0724   -0.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    0.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005   -0.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379    0.9720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131    0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554    1.4863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785    1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750    1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136   -0.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    2.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9359    1.6298    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  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
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
  7 15  1  0  0  0  0
  5 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243538

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC2(C)C1N(C)C1=C2C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O/c1-13-6-7-14(2)12(13)15(3)11-5-4-9(16)8-10(11)13/h4-5,8,12,16H,6-7H2,1-3H3

> <INCHI_KEY>
HKGWQUVGHPDEBZ-UHFFFAOYSA-N

> <FORMULA>
C13H18N2O

> <MOLECULAR_WEIGHT>
218.3

> <EXACT_MASS>
218.141913208

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.58606251900131

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-ol

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
2.431576245333334

> <ALOGPS_LOGS>
-1.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.241503654644271

> <JCHEM_PKA_STRONGEST_BASIC>
6.701067788589561

> <JCHEM_POLAR_SURFACE_AREA>
26.71

> <JCHEM_REFRACTIVITY>
65.6719

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3a,8-trimethyl-2H,3H,8aH-pyrrolo[2,3-b]indol-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0251948
     RDKit          3D
Eseroline
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.7800   -0.6552    1.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6967    0.1509    0.8939 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.5441    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6967    2.0773    0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342    0.9453   -0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    1.3867   -2.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713    0.3949   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849    1.0231   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678    0.2667    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6110    0.8611    0.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2361   -1.1097    0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0274   -1.7322    0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -0.9660   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.3828   -0.3525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8584   -2.7416   -0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938   -0.2058   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4456   -1.1725    2.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1678   -1.3686    0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    0.0210    1.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3642    2.0484    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7501    1.6479   -0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359    2.1235    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7734    3.0300   -0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553    2.4351   -2.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7999    1.4389   -2.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    0.6659   -2.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4273    2.0938   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8076    1.1966    1.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0789   -1.7065    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9604   -2.7995    0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730   -2.8198   -1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2861   -3.0886    0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376   -3.3686   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820   -0.2337   -1.1778 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16  2  1  0
 16  5  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       3.868  -1.065   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.373   0.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.601  -0.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.864   0.341   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.417   1.814   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.878   1.845   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.650   2.774   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.387   1.894   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.833   0.420   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.781  -0.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.281  -0.354   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.166   1.120   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.887   2.244   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.772  -1.478   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.680   4.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.347   3.042   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6    9                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11                                                            
CONECT   15    7                                                            
CONECT   16    5                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0243538
HETATM    1  C1  UNL     1      -3.480   0.201   0.237  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.220   0.040  -0.432  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.103  -1.192  -1.151  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.587  -1.264  -1.383  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.110  -0.971   0.018  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.195  -2.181   0.908  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.219  -0.359   0.094  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.509  -0.822   0.127  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.601   0.030   0.207  1.00  0.00           C  
HETATM   10  O1  UNL     1       4.895  -0.467   0.239  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.413   1.390   0.258  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.132   1.881   0.227  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.045   1.005   0.145  1.00  0.00           C  
HETATM   14  N2  UNL     1      -0.344   1.297   0.095  1.00  0.00           N  
HETATM   15  C12 UNL     1      -0.910   2.600  -0.248  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.087   0.112   0.435  1.00  0.00           C  
HETATM   17  H1  UNL     1      -4.124   0.874  -0.393  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.392   0.658   1.232  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.000  -0.791   0.266  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.402  -2.049  -0.538  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.644  -1.179  -2.116  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.292  -0.424  -2.042  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.282  -2.242  -1.763  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.426  -2.975   0.438  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.315  -1.934   1.867  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.235  -2.501   1.072  1.00  0.00           H  
HETATM   27  H11 UNL     1       2.644  -1.905   0.086  1.00  0.00           H  
HETATM   28  H12 UNL     1       5.373  -0.701   1.113  1.00  0.00           H  
HETATM   29  H13 UNL     1       4.262   2.077   0.322  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.945   2.957   0.265  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.344   3.340   0.385  1.00  0.00           H  
HETATM   32  H16 UNL     1      -0.726   2.817  -1.328  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.968   2.605   0.027  1.00  0.00           H  
HETATM   34  H18 UNL     1      -1.334   0.074   1.507  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   16
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6    7   16
CONECT    6   24   25   26
CONECT    7    8    8   13
CONECT    8    9   27
CONECT    9   10   11   11
CONECT   10   28
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14
CONECT   14   15   16
CONECT   15   31   32   33
CONECT   16   34
END

HMDB0251948
     RDKit          3D
Eseroline
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.7800   -0.6552    1.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6967    0.1509    0.8939 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.5441    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6967    2.0773    0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342    0.9453   -0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    1.3867   -2.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713    0.3949   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849    1.0231   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678    0.2667    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6110    0.8611    0.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2361   -1.1097    0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0274   -1.7322    0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -0.9660   -0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.3828   -0.3525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8584   -2.7416   -0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938   -0.2058   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4456   -1.1725    2.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1678   -1.3686    0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    0.0210    1.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3642    2.0484    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7501    1.6479   -0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359    2.1235    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7734    3.0300   -0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553    2.4351   -2.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7999    1.4389   -2.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    0.6659   -2.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4273    2.0938   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8076    1.1966    1.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0789   -1.7065    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9604   -2.7995    0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730   -2.8198   -1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2861   -3.0886    0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376   -3.3686   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820   -0.2337   -1.1778 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16  2  1  0
 16  5  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈N₂O

Average Molecular Weight

218.3

Monoisotopic Molecular Weight

218.141913208

IUPAC Name

1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-ol

Traditional Name

1,3a,8-trimethyl-2H,3H,8aH-pyrrolo[2,3-b]indol-5-ol

CAS Registry Number

Not Available

SMILES

CN1CCC2(C)C1N(C)C1=C2C=C(O)C=C1

InChI Identifier

InChI=1S/C13H18N2O/c1-13-6-7-14(2)12(13)15(3)11-5-4-9(16)8-10(11)13/h4-5,8,12,16H,6-7H2,1-3H3

InChI Key

HKGWQUVGHPDEBZ-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
Indole
Dialkylarylamine
1-hydroxy-2-unsubstituted benzenoid
N-alkylpyrrolidine
Benzenoid
Pyrrole
Pyrrolidine
Azacycle
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
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)

Source

Exogenous

Exogenous (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	1.75	ALOGPS
logP	2.43	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	10.24	ChemAxon
pKa (Strongest Basic)	6.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.71 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.67 m³·mol⁻¹	ChemAxon
Polarizability	24.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	150.215	30932474
DeepCCS	[M-H]-	147.819	30932474
DeepCCS	[M-2H]-	180.938	30932474
DeepCCS	[M+Na]+	156.219	30932474
AllCCS	[M+H]+	149.3	32859911
AllCCS	[M+H-H2O]+	145.4	32859911
AllCCS	[M+NH4]+	153.0	32859911
AllCCS	[M+Na]+	154.1	32859911
AllCCS	[M-H]-	155.5	32859911
AllCCS	[M+Na-2H]-	155.5	32859911
AllCCS	[M+HCOO]-	155.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Eseroline	CN1CCC2(C)C1N(C)C1=C2C=C(O)C=C1	1880.2	Standard non polar	33892256
(+)-Eseroline	CN1CCC2(C)C1N(C)C1=C2C=C(O)C=C1	1880.2	Standard non polar	33892256
(+)-Eseroline	CN1CCC2(C)C1N(C)C1=C2C=C(O)C=C1	1882.2	Semi standard non polar	33892256
(+)-Eseroline	CN1CCC2(C)C1N(C)C1=C2C=C(O)C=C1	1882.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-Eseroline,1TMS,isomer #1	CN1CCC2(C)C3=CC(O[Si](C)(C)C)=CC=C3N(C)C12	1891.2	Semi standard non polar	33892256
(+)-Eseroline,1TMS,isomer #1	CN1CCC2(C)C3=CC(O[Si](C)(C)C)=CC=C3N(C)C12	1844.4	Standard non polar	33892256
(+)-Eseroline,1TMS,isomer #1	CN1CCC2(C)C3=CC(O[Si](C)(C)C)=CC=C3N(C)C12	2141.9	Standard polar	33892256
(+)-Eseroline,1TBDMS,isomer #1	CN1CCC2(C)C3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3N(C)C12	2131.9	Semi standard non polar	33892256
(+)-Eseroline,1TBDMS,isomer #1	CN1CCC2(C)C3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3N(C)C12	2087.4	Standard non polar	33892256
(+)-Eseroline,1TBDMS,isomer #1	CN1CCC2(C)C3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3N(C)C12	2309.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Eseroline GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0910000000-c216f4af754830f19f6c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Eseroline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Eseroline 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Eseroline 120V, Positive-QTOF	splash10-0002-5900000000-3b1f3148286d87fd4ba9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Eseroline 90V, Positive-QTOF	splash10-0002-3900000000-f1ac9aff15dd13f77c2c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Eseroline 75V, Positive-QTOF	splash10-01pk-2900000000-d437dfc94a36b7506ff7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Eseroline 15V, Positive-QTOF	splash10-03di-0900000000-f520ae07d6f1b25d9e0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Eseroline 30V, Positive-QTOF	splash10-03di-0900000000-660561d818ec1089f68a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Eseroline 60V, Positive-QTOF	splash10-03di-1900000000-da8573567948bee5f48d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Eseroline 45V, Positive-QTOF	splash10-03di-0900000000-66f42c7668c44d82e26d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Eseroline 10V, Positive-QTOF	splash10-014i-0090000000-4f79e559c5057cb29231	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Eseroline 20V, Positive-QTOF	splash10-03y0-0920000000-c007412868e436860f49	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Eseroline 40V, Positive-QTOF	splash10-03di-0900000000-1feb0faa51b7e7983084	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Eseroline 10V, Negative-QTOF	splash10-014i-0090000000-09dd32e79c2ea83c7941	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Eseroline 20V, Negative-QTOF	splash10-02t9-0690000000-2f2757794bb3baee7e14	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Eseroline 40V, Negative-QTOF	splash10-03ki-0900000000-4fbf0d4ab46fefe0ab14	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

1212

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1250

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 (+)-Eseroline (HMDB0243538)

MOL for HMDB0243538 ((+)-Eseroline)

3D MOL for HMDB0243538 ((+)-Eseroline)

3D SDF for HMDB0243538 ((+)-Eseroline)

3D-SDF for HMDB0243538 ((+)-Eseroline)

PDB for HMDB0243538 ((+)-Eseroline)

3D PDB for HMDB0243538 ((+)-Eseroline)

SMILES for HMDB0243538 ((+)-Eseroline)

INCHI for HMDB0243538 ((+)-Eseroline)

Structure for HMDB0243538 ((+)-Eseroline)

3D Structure for HMDB0243538 ((+)-Eseroline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra