NP-MRD: Showing NP-Card for 3-(thiophen-2-yl)-2,2'-bithiophene (NP0173241)

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Record Information

Version

2.0

Created at

2022-09-03 10:20:46 UTC

Updated at

2022-09-03 10:20:47 UTC

NP-MRD ID

NP0173241

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(thiophen-2-yl)-2,2'-bithiophene

Description

2,2':3',2''-Terthiophene 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. 3-(thiophen-2-yl)-2,2'-bithiophene is found in Eclipta prostrata. 3-(thiophen-2-yl)-2,2'-bithiophene was first documented in 2015 (PMID: 25815088). Based on a literature review a small amount of articles have been published on 2,2':3',2''-Terthiophene (PMID: 30027738) (PMID: 26632006) (PMID: 25451463).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032212202D          

 15 17  0  0  0  0            999 V2000
    3.4719   -0.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -0.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -0.1802    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594    0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594    1.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919    1.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469    2.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719    2.3993    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268    1.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5114    1.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789    1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8463    1.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914    0.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7664    0.5751    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268   -0.1802    0.0000 C   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  2  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
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
  4 15  2  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173241

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
SBVKMIQOXJYJIM-UHFFFAOYSA-N

> <FORMULA>
C12H8S3

> <MOLECULAR_WEIGHT>
248.38

> <EXACT_MASS>
247.97881378

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
25.52047249518363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(thiophen-2-yl)-2,2'-bithiophene

> <ALOGPS_LOGP>
5.38

> <JCHEM_LOGP>
4.599140659

> <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>
67.0001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(thiophen-2-yl)-2,2'-bithiophene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       6.481  -1.801   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.941  -1.801   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       4.465  -0.336   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0       5.711   0.569   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.711   2.109   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.465   3.014   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.941   4.479   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       6.481   4.479   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0       6.957   3.014   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.421   2.538   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.667   3.443   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.913   2.538   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.437   1.073   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0       8.897   1.073   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       6.957  -0.336   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15    4    1                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₈S₃

Average Mass

248.3800 Da

Monoisotopic Mass

247.97881 Da

IUPAC Name

3-(thiophen-2-yl)-2,2'-bithiophene

Traditional Name

3-(thiophen-2-yl)-2,2'-bithiophene

CAS Registry Number

Not Available

SMILES

S1C=CC=C1C1=C(C=CS1)C1=CC=CS1

InChI Identifier

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

InChI Key

SBVKMIQOXJYJIM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eclipta prostrata	LOTUS Database	35616633

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
Heteroaromatic compound
Thiophene
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

terthiophene (CHEBI:50079 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	5.38	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	67 m³·mol⁻¹	ChemAxon
Polarizability	25.52 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

350618

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

395532

PDB ID

Not Available

ChEBI ID

50079

Good Scents ID

Not Available

References

General References

Strudwick BH, Zhang J, Hilbers MF, Buma WJ, Woutersen S, Liu SH, Hartl F: Excited-State Electronic Asymmetry Prevents Photoswitching in Terthiophene Compounds. Inorg Chem. 2018 Aug 6;57(15):9039-9047. doi: 10.1021/acs.inorgchem.8b01005. Epub 2018 Jul 20. [PubMed:30027738 ]
Zhang J, Sun CF, Zhang MX, Hartl F, Yin J, Yu GA, Rao L, Liu SH: Asymmetric oxidation of vinyl- and ethynyl terthiophene ligands in triruthenium complexes. Dalton Trans. 2016 Jan 14;45(2):768-82. doi: 10.1039/c5dt04083c. [PubMed:26632006 ]
Goll M, Ruff A, Muks E, Goerigk F, Omiecienski B, Ruff I, Gonzalez-Cano RC, Lopez Navarrete JT, Ruiz Delgado MC, Ludwigs S: Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization "click"-reactions. Beilstein J Org Chem. 2015 Mar 11;11:335-47. doi: 10.3762/bjoc.11.39. eCollection 2015. [PubMed:25815088 ]
Scheuble M, Goll M, Ludwigs S: Branched terthiophenes in organic electronics: from small molecules to polymers. Macromol Rapid Commun. 2015 Jan;36(2):115-37. doi: 10.1002/marc.201400525. Epub 2014 Nov 29. [PubMed:25451463 ]
LOTUS database [Link]

Showing NP-Card for 3-(thiophen-2-yl)-2,2'-bithiophene (NP0173241)

MOL for NP0173241 (3-(thiophen-2-yl)-2,2'-bithiophene)

3D MOL for NP0173241 (3-(thiophen-2-yl)-2,2'-bithiophene)

3D SDF for NP0173241 (3-(thiophen-2-yl)-2,2'-bithiophene)

3D-SDF for NP0173241 (3-(thiophen-2-yl)-2,2'-bithiophene)

PDB for NP0173241 (3-(thiophen-2-yl)-2,2'-bithiophene)

3D PDB for NP0173241 (3-(thiophen-2-yl)-2,2'-bithiophene)

SMILES for NP0173241 (3-(thiophen-2-yl)-2,2'-bithiophene)

INCHI for NP0173241 (3-(thiophen-2-yl)-2,2'-bithiophene)

Structure for NP0173241 (3-(thiophen-2-yl)-2,2'-bithiophene)

3D Structure for NP0173241 (3-(thiophen-2-yl)-2,2'-bithiophene)