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Showing metabocard for 2,2'-Bithiophene (HMDB0245353)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:25:55 UTC
Update Date2021-09-26 22:53:47 UTC
HMDB IDHMDB0245353
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,2'-Bithiophene
Description2,2'-Bithiophene, also known as 2,2'-dithienyl or alpha-bithiophene, 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. Thus, 2,2'-bithiophene is considered to be an oxygenated hydrocarbon. Based on a literature review very few articles have been published on 2,2'-Bithiophene. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,2'-bithiophene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,2'-Bithiophene 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 HMDB0245353 (2,2'-Bithiophene)


  Mrv1652309112100262D          

 10 11  0  0  0  0            999 V2000
    1.6689   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890    0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689    1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239    0.3047    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
M  END
Download

3D MOL for HMDB0245353 (2,2'-Bithiophene)

HMDB0245353
     RDKit          3D
2,2'-Bithiophene
 16 17  0  0  0  0  0  0  0  0999 V2000
    2.8529   -0.7240    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2837    0.2392   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    1.0500   -1.1876 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    0.1457   -0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124    0.3357   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -0.3426    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8983    0.0400    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1931    1.0963   -0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6401    1.5193   -0.9623 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5401   -0.7730    0.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5912   -1.4241    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3239    0.4248   -1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885   -1.1883    1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7321   -0.4462    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1525    1.5611   -0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685   -1.5141    1.0586 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
  4 10  2  0
 10  1  1  0
  9  5  1  0
  1 11  1  0
  2 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
 10 16  1  0
M  END
Download

3D SDF for HMDB0245353 (2,2'-Bithiophene)


  Mrv1652309112100262D          

 10 11  0  0  0  0            999 V2000
    1.6689   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890    0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689    1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239    0.3047    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
M  END
> <DATABASE_ID>
HMDB0245353

> <DATABASE_NAME>
hmdb

> <SMILES>
S1C=CC=C1C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C8H6S2/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6H

> <INCHI_KEY>
OHZAHWOAMVVGEL-UHFFFAOYSA-N

> <FORMULA>
C8H6S2

> <MOLECULAR_WEIGHT>
166.26

> <EXACT_MASS>
165.991092541

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
17.218118863295672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2'-bithiophene

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
3.174767257333333

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
44.974000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2'-bithiophene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0245353 (2,2'-Bithiophene)

HMDB0245353
     RDKit          3D
2,2'-Bithiophene
 16 17  0  0  0  0  0  0  0  0999 V2000
    2.8529   -0.7240    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2837    0.2392   -0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    1.0500   -1.1876 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    0.1457   -0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124    0.3357   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -0.3426    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8983    0.0400    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1931    1.0963   -0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6401    1.5193   -0.9623 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5401   -0.7730    0.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5912   -1.4241    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3239    0.4248   -1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885   -1.1883    1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7321   -0.4462    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1525    1.5611   -0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685   -1.5141    1.0586 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
  4 10  2  0
 10  1  1  0
  9  5  1  0
  1 11  1  0
  2 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
 10 16  1  0
M  END
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PDB for HMDB0245353 (2,2'-Bithiophene)

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       3.115  -4.246   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.575  -4.246   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       1.099  -2.782   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0       2.345  -1.876   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.591  -2.782   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.345  -0.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.099   0.569   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.575   2.033   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.115   2.033   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0       3.591   0.569   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                                                       
CONECT   10    9    6                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0245353 (2,2'-Bithiophene)

COMPND    HMDB0245353
HETATM    1  C1  UNL     1       2.853  -0.724   0.094  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.284   0.239  -0.774  1.00  0.00           C  
HETATM    3  S1  UNL     1       1.838   1.050  -1.188  1.00  0.00           S  
HETATM    4  C3  UNL     1       0.744   0.146  -0.251  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.712   0.336  -0.151  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.624  -0.343   0.568  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.898   0.040   0.477  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.193   1.096  -0.341  1.00  0.00           C  
HETATM    9  S2  UNL     1      -1.640   1.519  -0.962  1.00  0.00           S  
HETATM   10  C8  UNL     1       1.540  -0.773   0.366  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.591  -1.424   0.541  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.324   0.425  -1.110  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.288  -1.188   1.205  1.00  0.00           H  
HETATM   14  H4  UNL     1      -3.732  -0.446   1.024  1.00  0.00           H  
HETATM   15  H5  UNL     1      -4.152   1.561  -0.555  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.068  -1.514   1.059  1.00  0.00           H  
CONECT    1    2    2   10   11
CONECT    2    3   12
CONECT    3    4
CONECT    4    5   10   10
CONECT    5    6    6    9
CONECT    6    7   13
CONECT    7    8    8   14
CONECT    8    9   15
CONECT   10   16
END
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SMILES for HMDB0245353 (2,2'-Bithiophene)

S1C=CC=C1C1=CC=CS1
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INCHI for HMDB0245353 (2,2'-Bithiophene)

InChI=1S/C8H6S2/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,2'-BithienylChEBI
2,2'-DithienylChEBI
2,2'-DithiopheneChEBI
2-(Thien-2-yl)thiopheneChEBI
alpha-BithiopheneChEBI
DithienylChEBI
a-BithiopheneGenerator
Α-bithiopheneGenerator
Chemical FormulaC8H6S2
Average Molecular Weight166.26
Monoisotopic Molecular Weight165.991092541
IUPAC Name2,2'-bithiophene
Traditional Name2,2'-bithiophene
CAS Registry NumberNot Available
SMILES
S1C=CC=C1C1=CC=CS1
InChI Identifier
InChI=1S/C8H6S2/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6H
InChI KeyOHZAHWOAMVVGEL-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
  • Heteroaromatic compound
  • Thiophene
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
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
logP4.06ALOGPS
logP3.17ChemAxon
logS-3.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.97 m³·mol⁻¹ChemAxon
Polarizability17.22 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+131.70330932474
DeepCCS[M-H]-129.44830932474
DeepCCS[M-2H]-165.10230932474
DeepCCS[M+Na]+139.32830932474
AllCCS[M+H]+129.032859911
AllCCS[M+H-H2O]+124.332859911
AllCCS[M+NH4]+133.532859911
AllCCS[M+Na]+134.832859911
AllCCS[M-H]-128.532859911
AllCCS[M+Na-2H]-129.432859911
AllCCS[M+HCOO]-130.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,2'-BithiopheneS1C=CC=C1C1=CC=CS12112.9Standard polar33892256
2,2'-BithiopheneS1C=CC=C1C1=CC=CS11392.2Standard non polar33892256
2,2'-BithiopheneS1C=CC=C1C1=CC=CS11435.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,2'-Bithiophene GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1900000000-39d63f25a482c44ff4972021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,2'-Bithiophene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2'-Bithiophene 10V, Positive-QTOFsplash10-014i-0900000000-8f3fca2144ea1a61e4a62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2'-Bithiophene 20V, Positive-QTOFsplash10-014i-0900000000-047313f733adda199ecd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2'-Bithiophene 40V, Positive-QTOFsplash10-01q9-4900000000-ad4c4a401f1ae9e8a28c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2'-Bithiophene 10V, Negative-QTOFsplash10-03di-0900000000-ca8134aa2740c55702a52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2'-Bithiophene 20V, Negative-QTOFsplash10-03di-0900000000-ca8134aa2740c55702a52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2'-Bithiophene 40V, Negative-QTOFsplash10-03di-0900000000-1ea72f6eaca9799c57b22021-10-12Wishart LabView Spectrum
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 IDC00049955
Chemspider ID61428
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,2'-Bithiophene
METLIN IDNot Available
PubChem Compound68120
PDB IDNot Available
ChEBI ID36821
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1158401
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 ]