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Showing metabocard for 2,2':5',2''-Terthiophene (HMDB0245378)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:27:13 UTC
Update Date2022-03-06 23:24:14 UTC
HMDB IDHMDB0245378
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,2':5',2''-Terthiophene
Description2,2':5',2''-Terthiophene, also known as terthiophene or alpha-terthienyl, belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms. Based on a literature review a significant number of articles have been published on 2,2':5',2''-Terthiophene. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,2':5',2''-terthiophene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,2':5',2''-Terthiophene 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0245378 (2,2':5',2''-Terthiophene)

  Mrv1533004191520082D          

 15 17  0  0  0  0            999 V2000
    3.4719   -3.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -3.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -2.8001    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594   -2.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268   -2.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -0.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -0.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268   -1.0052    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9568    0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7019    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3693    1.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0367    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7818    0.4468    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
M  END
Download

3D MOL for HMDB0245378 (2,2':5',2''-Terthiophene)

HMDB0245378
     RDKit          3D
2,2':5',2''-Terthiophene
 23 25  0  0  0  0  0  0  0  0999 V2000
   -4.9881    0.0709   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9000    0.1390   -1.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2160    0.1392   -2.0955 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770    0.0538   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    0.0196   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065   -0.0483    1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274   -0.0670    1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2893   -0.0161    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7623   -0.0224    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6952   -0.0797    1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919   -0.0709    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2472   -0.0055   -0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6890    0.0418   -1.2676 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1253    0.0557   -0.9738 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8385    0.0271    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9864    0.0538    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7553    0.1810   -2.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270   -0.0852    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045   -0.1217    2.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3619   -0.1303    2.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8282   -0.1148    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2522    0.0095   -1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7906   -0.0294    1.3455 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 14  1  0
  4 15  2  0
 15  1  1  0
 14  5  1  0
 13  9  1  0
  1 16  1  0
  2 17  1  0
  6 18  1  0
  7 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 15 23  1  0
M  END
Download

3D SDF for HMDB0245378 (2,2':5',2''-Terthiophene)

  Mrv1533004191520082D          

 15 17  0  0  0  0            999 V2000
    3.4719   -3.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -3.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -2.8001    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594   -2.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268   -2.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -0.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719   -0.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268   -1.0052    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9568    0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7019    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3693    1.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0367    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7818    0.4468    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245378

> <DATABASE_NAME>
hmdb

> <SMILES>
S1C=CC=C1C1=CC=C(S1)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H

> <INCHI_KEY>
KXSFECAJUBPPFE-UHFFFAOYSA-N

> <FORMULA>
C12H8S3

> <MOLECULAR_WEIGHT>
248.38

> <EXACT_MASS>
247.97881378

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
26.50501626818871

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-bis(thiophen-2-yl)thiophene

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
4.595846745666666

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
66.7842

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
terthiophene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0245378 (2,2':5',2''-Terthiophene)

HMDB0245378
     RDKit          3D
2,2':5',2''-Terthiophene
 23 25  0  0  0  0  0  0  0  0999 V2000
   -4.9881    0.0709   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9000    0.1390   -1.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2160    0.1392   -2.0955 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770    0.0538   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    0.0196   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065   -0.0483    1.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274   -0.0670    1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2893   -0.0161    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7623   -0.0224    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6952   -0.0797    1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919   -0.0709    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2472   -0.0055   -0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6890    0.0418   -1.2676 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1253    0.0557   -0.9738 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8385    0.0271    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9864    0.0538    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7553    0.1810   -2.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270   -0.0852    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045   -0.1217    2.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3619   -0.1303    2.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8282   -0.1148    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2522    0.0095   -1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7906   -0.0294    1.3455 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 14  1  0
  4 15  2  0
 15  1  1  0
 14  5  1  0
 13  9  1  0
  1 16  1  0
  2 17  1  0
  6 18  1  0
  7 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 15 23  1  0
M  END
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PDB for HMDB0245378 (2,2':5',2''-Terthiophene)

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       6.481  -6.691   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.941  -6.691   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       4.465  -5.227   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0       5.711  -4.322   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.957  -5.227   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.711  -2.782   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.465  -1.876   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.941  -0.412   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.481  -0.412   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0       6.957  -1.876   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0       7.386   0.834   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.910   2.299   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.156   3.204   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.402   2.299   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0       8.926   0.834   0.000  0.00  0.00           S+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    6                                                       
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END
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3D PDB for HMDB0245378 (2,2':5',2''-Terthiophene)

COMPND    HMDB0245378
HETATM    1  C1  UNL     1      -4.988   0.071  -0.455  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.900   0.139  -1.822  1.00  0.00           C  
HETATM    3  S1  UNL     1      -3.216   0.139  -2.095  1.00  0.00           S  
HETATM    4  C3  UNL     1      -2.677   0.054  -0.485  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.289   0.020  -0.029  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.807  -0.048   1.245  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.527  -0.067   1.402  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.289  -0.016   0.269  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.762  -0.022   0.157  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.695  -0.080   1.146  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.992  -0.071   0.762  1.00  0.00           C  
HETATM   12  C11 UNL     1       5.247  -0.006  -0.578  1.00  0.00           C  
HETATM   13  S2  UNL     1       3.689   0.042  -1.268  1.00  0.00           S  
HETATM   14  S3  UNL     1       0.125   0.056  -0.974  1.00  0.00           S  
HETATM   15  C12 UNL     1      -3.838   0.027   0.232  1.00  0.00           C  
HETATM   16  H1  UNL     1      -5.986   0.054   0.045  1.00  0.00           H  
HETATM   17  H2  UNL     1      -5.755   0.181  -2.520  1.00  0.00           H  
HETATM   18  H3  UNL     1      -1.527  -0.085   2.095  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.004  -0.122   2.413  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.362  -0.130   2.204  1.00  0.00           H  
HETATM   21  H6  UNL     1       5.828  -0.115   1.500  1.00  0.00           H  
HETATM   22  H7  UNL     1       6.252   0.010  -1.038  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.791  -0.029   1.345  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3   17
CONECT    3    4
CONECT    4    5   15   15
CONECT    5    6    6   14
CONECT    6    7   18
CONECT    7    8    8   19
CONECT    8    9   14
CONECT    9   10   10   13
CONECT   10   11   20
CONECT   11   12   12   21
CONECT   12   13   22
CONECT   15   23
END
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SMILES for HMDB0245378 (2,2':5',2''-Terthiophene)

S1C=CC=C1C1=CC=C(S1)C1=CC=CS1
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INCHI for HMDB0245378 (2,2':5',2''-Terthiophene)

InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,2',5',2''-TerthienylChEBI
alpha-TerthienylChEBI
alpha-TerthiopheneChEBI
TerthiopheneChEBI
a-TerthienylGenerator
Α-terthienylGenerator
a-TerthiopheneGenerator
Α-terthiopheneGenerator
2,2,5,2''-TerthiopheneHMDB
Chemical FormulaC12H8S3
Average Molecular Weight248.38
Monoisotopic Molecular Weight247.97881378
IUPAC Name2,5-bis(thiophen-2-yl)thiophene
Traditional Nameterthiophene
CAS Registry NumberNot Available
SMILES
S1C=CC=C1C1=CC=C(S1)C1=CC=CS1
InChI Identifier
InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H
InChI KeyKXSFECAJUBPPFE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBi- and oligothiophenes
Sub ClassNot Available
Direct ParentBi- and oligothiophenes
Alternative Parents
Substituents
  • Bithiophene
  • 2,5-disubstituted thiophene
  • Heteroaromatic compound
  • Thiophene
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.11ALOGPS
logP4.6ChemAxon
logS-3.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.78 m³·mol⁻¹ChemAxon
Polarizability26.51 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001294
Chemspider ID58578
KEGG Compound IDC08460
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound65067
PDB IDNot Available
ChEBI ID10335
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1158741
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]