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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:24:11 UTC

Update Date

2021-09-26 23:04:01 UTC

HMDB ID

HMDB0251788

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Encenicline

Description

Encenicline belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system. Based on a literature review a significant number of articles have been published on Encenicline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Encenicline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Encenicline 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

HMDB0251788
     RDKit          3D
Encenicline
 38 41  0  0  0  0  0  0  0  0999 V2000
    0.2266    1.7225    2.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215    0.9544    1.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4800    0.3481    0.4722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8918    0.5780    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5412    1.1048   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8841    0.5739   -0.7262 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5837    0.7369    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0287   -0.3129    1.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6083   -0.7115    1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7040   -1.5154   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586   -0.8502   -1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561    0.7132    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339   -0.0759    0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847   -0.1320    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6882   -0.8711   -0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0377   -0.8247   -0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7291   -0.0872    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9477    0.6391    1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6446    1.6371    2.3629 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5526    0.5978    0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2991    1.3451    1.8651 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -0.2769   -0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357    1.2828    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6641    2.2065   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190    0.9679   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4922    1.7625    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6770    0.5791    0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6996   -1.1748    1.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233    0.1196    2.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557   -1.2742    1.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8011   -1.2849   -0.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -2.5739   -0.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891   -1.2837   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184   -1.0703   -2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8495   -0.6133   -0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2583   -1.4821   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6710   -1.3971   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7868   -0.0571    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
  9  4  1  0
 21 12  1  0
 11  6  1  0
 20 14  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END


  Mrv1652309112111242D          

 21 24  0  0  0  0            999 V2000
   -0.9560   -4.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9560   -4.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -3.6226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330   -4.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330   -4.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -5.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1041   -4.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1041   -4.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6104   -5.2726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249   -4.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249   -4.0351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393   -5.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1256   -6.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9325   -6.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450   -5.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7930   -4.9370    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1700   -5.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825   -6.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1700   -6.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450   -6.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825   -4.8356    0.0000 Cl  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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
 12 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 17 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251788

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=CC2=C1SC(=C2)C(=O)NC1CN2CCC1CC2

> <INCHI_IDENTIFIER>
InChI=1S/C16H17ClN2OS/c17-12-3-1-2-11-8-14(21-15(11)12)16(20)18-13-9-19-6-4-10(13)5-7-19/h1-3,8,10,13H,4-7,9H2,(H,18,20)

> <INCHI_KEY>
SSRDSYXGYPJKRR-UHFFFAOYSA-N

> <FORMULA>
C16H17ClN2OS

> <MOLECULAR_WEIGHT>
320.84

> <EXACT_MASS>
320.075012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
33.64640275259029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{1-azabicyclo[2.2.2]octan-3-yl}-7-chloro-1-benzothiophene-2-carboxamide

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
3.035720071

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.41992891035025

> <JCHEM_PKA_STRONGEST_BASIC>
7.277528906098705

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
85.9324

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{1-azabicyclo[2.2.2]octan-3-yl}-7-chloro-1-benzothiophene-2-carboxamide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0251788
     RDKit          3D
Encenicline
 38 41  0  0  0  0  0  0  0  0999 V2000
    0.2266    1.7225    2.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215    0.9544    1.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4800    0.3481    0.4722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8918    0.5780    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5412    1.1048   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8841    0.5739   -0.7262 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5837    0.7369    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0287   -0.3129    1.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6083   -0.7115    1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7040   -1.5154   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586   -0.8502   -1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561    0.7132    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339   -0.0759    0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847   -0.1320    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6882   -0.8711   -0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0377   -0.8247   -0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7291   -0.0872    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9477    0.6391    1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6446    1.6371    2.3629 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5526    0.5978    0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2991    1.3451    1.8651 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -0.2769   -0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357    1.2828    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6641    2.2065   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190    0.9679   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4922    1.7625    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6770    0.5791    0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6996   -1.1748    1.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233    0.1196    2.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557   -1.2742    1.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8011   -1.2849   -0.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -2.5739   -0.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891   -1.2837   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184   -1.0703   -2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8495   -0.6133   -0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2583   -1.4821   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6710   -1.3971   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7868   -0.0571    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
  9  4  1  0
 21 12  1  0
 11  6  1  0
 20 14  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  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      -1.785  -8.815   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.785  -7.789   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.528  -6.762   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.862  -7.532   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.862  -9.072   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.528  -9.842   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.194  -9.072   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.194  -7.532   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.139  -9.842   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.473  -9.072   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.473  -7.532   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.807  -9.842   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.968 -11.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.474 -11.694   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.244 -10.360   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       5.214  -9.216   0.000  0.00  0.00           S+0
HETATM   17  C   UNK     0       7.784 -10.360   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.554 -11.694   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.784 -13.028   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.244 -13.028   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       8.554  -9.027   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   12                                                       
CONECT   17   15   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14                                                       
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0251788
HETATM    1  O1  UNL     1       0.227   1.722   2.212  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.521   0.954   1.267  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.480   0.348   0.472  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.892   0.578   0.702  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.541   1.105  -0.559  1.00  0.00           C  
HETATM    6  N2  UNL     1      -3.884   0.574  -0.726  1.00  0.00           N  
HETATM    7  C4  UNL     1      -4.584   0.737   0.539  1.00  0.00           C  
HETATM    8  C5  UNL     1      -4.029  -0.313   1.487  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.608  -0.711   1.049  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.704  -1.515  -0.256  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.859  -0.850  -1.014  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.956   0.713   1.025  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.534  -0.076   0.066  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.885  -0.132   0.050  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.688  -0.871  -0.838  1.00  0.00           C  
HETATM   16  C13 UNL     1       6.038  -0.825  -0.726  1.00  0.00           C  
HETATM   17  C14 UNL     1       6.729  -0.087   0.220  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.948   0.639   1.093  1.00  0.00           C  
HETATM   19 CL1  UNL     1       6.645   1.637   2.363  1.00  0.00          CL  
HETATM   20  C16 UNL     1       4.553   0.598   0.985  1.00  0.00           C  
HETATM   21  S1  UNL     1       3.299   1.345   1.865  1.00  0.00           S  
HETATM   22  H1  UNL     1      -0.152  -0.277  -0.295  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.036   1.283   1.553  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.664   2.206  -0.407  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.919   0.968  -1.451  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.492   1.762   0.943  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.677   0.579   0.345  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.700  -1.175   1.467  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.923   0.120   2.485  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.156  -1.274   1.861  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.801  -1.285  -0.850  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.880  -2.574  -0.080  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.789  -1.284  -0.594  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.818  -1.070  -2.094  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.849  -0.613  -0.631  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.258  -1.482  -1.616  1.00  0.00           H  
HETATM   37  H16 UNL     1       6.671  -1.397  -1.413  1.00  0.00           H  
HETATM   38  H17 UNL     1       7.787  -0.057   0.300  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4   22
CONECT    4    5    9   23
CONECT    5    6   24   25
CONECT    6    7   11
CONECT    7    8   26   27
CONECT    8    9   28   29
CONECT    9   10   30
CONECT   10   11   31   32
CONECT   11   33   34
CONECT   12   13   13   21
CONECT   13   14   35
CONECT   14   15   15   20
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18   38
CONECT   18   19   20   20
CONECT   20   21
END

HMDB0251788
     RDKit          3D
Encenicline
 38 41  0  0  0  0  0  0  0  0999 V2000
    0.2266    1.7225    2.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215    0.9544    1.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4800    0.3481    0.4722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8918    0.5780    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5412    1.1048   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8841    0.5739   -0.7262 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5837    0.7369    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0287   -0.3129    1.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6083   -0.7115    1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7040   -1.5154   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586   -0.8502   -1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561    0.7132    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339   -0.0759    0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847   -0.1320    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6882   -0.8711   -0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0377   -0.8247   -0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7291   -0.0872    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9477    0.6391    1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6446    1.6371    2.3629 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5526    0.5978    0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2991    1.3451    1.8651 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -0.2769   -0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357    1.2828    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6641    2.2065   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190    0.9679   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4922    1.7625    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6770    0.5791    0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6996   -1.1748    1.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233    0.1196    2.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557   -1.2742    1.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8011   -1.2849   -0.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -2.5739   -0.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891   -1.2837   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184   -1.0703   -2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8495   -0.6133   -0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2583   -1.4821   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6710   -1.3971   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7868   -0.0571    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
  9  4  1  0
 21 12  1  0
 11  6  1  0
 20 14  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₇ClN₂OS

Average Molecular Weight

320.84

Monoisotopic Molecular Weight

320.075012

IUPAC Name

N-{1-azabicyclo[2.2.2]octan-3-yl}-7-chloro-1-benzothiophene-2-carboxamide

Traditional Name

N-{1-azabicyclo[2.2.2]octan-3-yl}-7-chloro-1-benzothiophene-2-carboxamide

CAS Registry Number

Not Available

SMILES

ClC1=CC=CC2=C1SC(=C2)C(=O)NC1CN2CCC1CC2

InChI Identifier

InChI=1S/C16H17ClN2OS/c17-12-3-1-2-11-8-14(21-15(11)12)16(20)18-13-9-19-6-4-10(13)5-7-19/h1-3,8,10,13H,4-7,9H2,(H,18,20)

InChI Key

SSRDSYXGYPJKRR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiophenes

Sub Class

1-benzothiophenes

Direct Parent

1-benzothiophenes

Alternative Parents

Substituents

1-benzothiophene
Quinuclidine
Thiophene carboxamide
Thiophene carboxylic acid or derivatives
2,3,5-trisubstituted thiophene
2-heteroaryl carboxamide
Piperidine
Benzenoid
Aryl halide
Aryl chloride
Heteroaromatic compound
Thiophene
Secondary carboxylic acid amide
Tertiary aliphatic amine
Carboxamide group
Tertiary amine
Amino acid or derivatives
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
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 (HMDB: HMDB0251788)

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	3.33	ALOGPS
logP	3.04	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	7.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.93 m³·mol⁻¹	ChemAxon
Polarizability	33.65 Å³	ChemAxon
Number of Rings	4	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]+	168.752	30932474
DeepCCS	[M-H]-	166.394	30932474
DeepCCS	[M-2H]-	199.279	30932474
DeepCCS	[M+Na]+	174.845	30932474
AllCCS	[M+H]+	171.0	32859911
AllCCS	[M+H-H2O]+	167.9	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.7	32859911
AllCCS	[M-H]-	174.6	32859911
AllCCS	[M+Na-2H]-	174.2	32859911
AllCCS	[M+HCOO]-	174.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.5695 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.24 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1150.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	245.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	86.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	324.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	373.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	309.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	743.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	359.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1170.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	297.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	444.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	155.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	32.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Encenicline	ClC1=CC=CC2=C1SC(=C2)C(=O)NC1CN2CCC1CC2	3636.8	Standard polar	33892256
Encenicline	ClC1=CC=CC2=C1SC(=C2)C(=O)NC1CN2CCC1CC2	2819.2	Standard non polar	33892256
Encenicline	ClC1=CC=CC2=C1SC(=C2)C(=O)NC1CN2CCC1CC2	3027.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Encenicline,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC2=CC=CC(Cl)=C2S1)C1CN2CCC1CC2	2696.6	Semi standard non polar	33892256
Encenicline,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC2=CC=CC(Cl)=C2S1)C1CN2CCC1CC2	2547.9	Standard non polar	33892256
Encenicline,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC2=CC=CC(Cl)=C2S1)C1CN2CCC1CC2	3414.5	Standard polar	33892256
Encenicline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC2=CC=CC(Cl)=C2S1)C1CN2CCC1CC2	2912.9	Semi standard non polar	33892256
Encenicline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC2=CC=CC(Cl)=C2S1)C1CN2CCC1CC2	2731.3	Standard non polar	33892256
Encenicline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC2=CC=CC(Cl)=C2S1)C1CN2CCC1CC2	3527.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Encenicline GC-MS (Non-derivatized) - 70eV, Positive	splash10-06r7-1900000000-020188af5bb0ade7aa34	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Encenicline 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 - Encenicline 10V, Positive-QTOF	splash10-00di-0009000000-0cff1d354d34df74a574	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encenicline 20V, Positive-QTOF	splash10-00di-0509000000-b9737af97d522bb09ae6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encenicline 40V, Positive-QTOF	splash10-03di-0900000000-88e523789d1e52e9e322	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encenicline 10V, Negative-QTOF	splash10-014i-0009000000-a041a90b112cee5b0e27	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encenicline 20V, Negative-QTOF	splash10-0159-6109000000-035b6c577744223273f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Encenicline 40V, Negative-QTOF	splash10-001i-9300000000-8c56eaaab6aae5eaa9ce	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

30922873

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Encenicline

METLIN ID

Not Available

PubChem Compound

66787058

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 Encenicline (HMDB0251788)

MOL for HMDB0251788 (Encenicline)

3D MOL for HMDB0251788 (Encenicline)

3D SDF for HMDB0251788 (Encenicline)

3D-SDF for HMDB0251788 (Encenicline)

PDB for HMDB0251788 (Encenicline)

3D PDB for HMDB0251788 (Encenicline)

SMILES for HMDB0251788 (Encenicline)

INCHI for HMDB0251788 (Encenicline)

Structure for HMDB0251788 (Encenicline)

3D Structure for HMDB0251788 (Encenicline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra