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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:27:13 UTC

Update Date

2022-03-06 23:24:14 UTC

HMDB ID

HMDB0245378

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,2':5',2''-Terthiophene

Description

2,2':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

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


  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

$$$$

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2',5',2''-Terthienyl	ChEBI
alpha-Terthienyl	ChEBI
alpha-Terthiophene	ChEBI
Terthiophene	ChEBI
a-Terthienyl	Generator
Α-terthienyl	Generator
a-Terthiophene	Generator
Α-terthiophene	Generator
2,2,5,2''-Terthiophene	HMDB

Chemical Formula

C₁₂H₈S₃

Average Molecular Weight

248.38

Monoisotopic Molecular Weight

247.97881378

IUPAC Name

2,5-bis(thiophen-2-yl)thiophene

Traditional Name

terthiophene

CAS Registry Number

Not 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 Key

KXSFECAJUBPPFE-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Bi- and oligothiophenes

Sub Class

Not Available

Direct Parent

Bi- and oligothiophenes

Alternative Parents

Substituents

Bithiophene
2,5-disubstituted thiophene
Heteroaromatic compound
Thiophene
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

terthiophene (CHEBI:10335 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Endogenous

Endogenous (HMDB: HMDB0245378)

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	5.11	ALOGPS
logP	4.6	ChemAxon
logS	-3.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.78 m³·mol⁻¹	ChemAxon
Polarizability	26.51 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]+	146.675	30932474
DeepCCS	[M-H]-	144.279	30932474
DeepCCS	[M-2H]-	178.703	30932474
DeepCCS	[M+Na]+	153.174	30932474
AllCCS	[M+H]+	150.5	32859911
AllCCS	[M+H-H2O]+	146.4	32859911
AllCCS	[M+NH4]+	154.4	32859911
AllCCS	[M+Na]+	155.5	32859911
AllCCS	[M-H]-	145.9	32859911
AllCCS	[M+Na-2H]-	145.3	32859911
AllCCS	[M+HCOO]-	144.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	18.5911 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.3 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2407.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	718.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	278.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	493.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	376.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	714.2 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	676.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	206.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1591.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	588.3 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	1486.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	586.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	450.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	602.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	561.4 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	75.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,2':5',2''-Terthiophene	S1C=CC=C1C1=CC=C(S1)C1=CC=CS1	3070.6	Standard polar	33892256
2,2':5',2''-Terthiophene	S1C=CC=C1C1=CC=C(S1)C1=CC=CS1	2257.9	Standard non polar	33892256
2,2':5',2''-Terthiophene	S1C=CC=C1C1=CC=C(S1)C1=CC=CS1	2241.1	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 - 2,2':5',2''-Terthiophene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2290000000-4908b53ee22ce52b0c29	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2':5',2''-Terthiophene 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 - 2,2':5',2''-Terthiophene 10V, Positive-QTOF	splash10-0002-0090000000-3a09a844519999fe6d52	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 20V, Positive-QTOF	splash10-0002-0090000000-31f666a4e7c618f2eadf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 40V, Positive-QTOF	splash10-0udi-4590000000-97d8b33af819504a23ab	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 10V, Negative-QTOF	splash10-0002-0090000000-4e9eadbcd8bb3ad50bd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 20V, Negative-QTOF	splash10-0002-0190000000-2fd292d7342fb9e5470c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 40V, Negative-QTOF	splash10-0a4i-9010000000-077d847fcbb812af84fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 10V, Positive-QTOF	splash10-0002-0090000000-ff371ae3fe94d7426390	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 20V, Positive-QTOF	splash10-0002-0090000000-ff371ae3fe94d7426390	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 40V, Positive-QTOF	splash10-03dj-0790000000-a35956c438af0d96d00d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 10V, Negative-QTOF	splash10-0002-0090000000-56ea90a33f87d10e6cfa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 20V, Negative-QTOF	splash10-0002-0090000000-56ea90a33f87d10e6cfa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2':5',2''-Terthiophene 40V, Negative-QTOF	splash10-0ika-0190000000-2b388a75f8a2519d0ebe	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

C00001294

Chemspider ID

58578

KEGG Compound ID

C08460

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65067

PDB ID

Not Available

ChEBI ID

10335

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1158741

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

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

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

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

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

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

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

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

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

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

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

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra