Common Name

Thiophene Description

Thiophene is a maillard product At room temperature, thiophene is a colorless liquid with a mildly pleasant odor reminiscent of benzene, with which thiophene shares some similarities. The high reactivity of thiophene toward slifonation is the basis for the separation of thiophene from benzene, which are difficlit to separate by distillation due to their similar boiling points (4 C difference at ambient pressure). Like benzene, thiophene forms an azeotrope with water. Not only is thiophene reactive toward electrophiles, it is also readily lithiated with butyl lithium to give 2-lithiothiophene, which is a precursor to a variety of derivatives, including dithienyl.Thiophene has been shown to exhibit antibiotic, anti-microbial, anti-inflammatory and anti-cancer functions (PMID 21443219 , 17070919 , 15358292 , 10462535 ).Thiophene belongs to the family of Thiophenes. These are compounds containing a five-member aromatic compound made up of one slifur atom and four carbon atoms. Structure

MOLSDFPDBSMILESInChI

Structure for HMDB29718 (Thiophene)

Synonyms

Value Source ThiofuranChEBI ThiophenChEBI 2-Thienylacetic acidHMDB 2-Thiopheneacetic acidHMDB Divinylene slifideHMDB Hopkin'S lactic acid reagentHMDB PolythiopheneHMDB ThiacyclopentadieneHMDB ThiapheneHMDB Thien-2-ylacetateHMDB thio-FuranHMDB ThiofenHMDB ThiofuramHMDB ThiofurfuranHMDB ThioleHMDB Thiophene, homopolymerHMDB ThiotetroleHMDB

Chemical Formlia

C4H4S Average Molecliar Weight

84.14 Monoisotopic Molecliar Weight

84.003370818 IUPAC Name

thiophene Traditional Name

thiophene CAS Registry Number

110-02-1 SMILES

S1C=CC=C1

InChI Identifier

InChI=1S/C4H4S/c1-2-4-5-3-1/h1-4H

InChI Key

YTPLMLYBLZKORZ-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as heteroaromatic compounds. These are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Heteroaromatic compounds Sub Class

Not Available Direct Parent

Heteroaromatic compounds Alternative Parents

  • Thiophenes
  • Hydrocarbon derivatives
  • Substituents

  • Heteroaromatic compound
  • Thiophene
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
  • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • thiophenes (CHEBI:30856 )
  • mancude organic heteromonocyclic parent (CHEBI:30856 )
  • monocyclic heteroarene (CHEBI:30856 )
  • Ontology Status

    Detected and Quantified Origin

  • Endogenous
  • Food
  • Biofunction

  • anti-cancer
  • anti-inflammatory
  • anti-microbial
  • Application

  • Nutrient
  • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Physical Properties State

    Not Available Experimental Properties

    Property Value Reference Melting Point-38.3 °CNot Available Boiling PointNot AvailableNot Available Water Solubility3.01 mg/mL at 25 °CNot Available LogP1.81Not Available

    Predicted Properties

    Property Value Source Water Solubility1.22 mg/mLALOGPS logP1.89ALOGPS logP1.75ChemAxon logS-1.8ALOGPS pKa (Strongest Basic)-7.8ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count0ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area0 Å2ChemAxon Rotatable Bond Count0ChemAxon Refractivity23.16 m3·mol-1ChemAxon Polarizability8.56 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Biofluid Locations

  • Feces
  • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details FecesDetected and Quantified0 – 2.81 ppmChildren (1-13 years old)Not Specified

    Normal

  • 21970810
  • details FecesDetected but not Quantified Adlit (>18 years old)BothNormal

  • 20055983
  • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details FecesDetected and Quantified0 – 12.47 ppmChildren (1-13 years old)Not Specified

    Treated celiac disease

  • 21970810
  • details

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB000912 KNApSAcK ID

    Not Available Chemspider ID

    7739 KEGG Compound ID

    C02595 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Thiophene NuGOwiki Link

    HMDB29718 Metagene Link

    HMDB29718 METLIN ID

    Not Available PubChem Compound

    8030 PDB ID

    Not Available ChEBI ID

    30856

    Product: Danirixin

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Wiles JA, Phadke AS, Bradbury BJ, Pucci MJ, Thanassi JA, Deshpande M: Selenophene-containing inhibitors of type IIA bacterial topoisomerases. J Med Chem. 2011 May 12;54(9):3418-25. doi: 10.1021/jm2002124. Epub 2011 Apr 13. [PubMed:21443219 ]
    2. Rodriguez-Arguelles MC, Mosquera-Vazquez S, Touron-Touceda P, Sanmartin-Matalobos J, Garcia-Deibe AM, Belicchi-Ferrari M, Pelosi G, Pelizzi C, Zani F: Complexes of 2-thiophenecarbonyl and isonicotinoyl hydrazones of 3-(N-methyl)isatin. A study of their antimicrobial activity. J Inorg Biochem. 2007 Jan;101(1):138-47. Epub 2006 Sep 19. [PubMed:17070919 ]
    3. Pillai AD, Rathod PD, Xavier FP, Vasu KK, Padh H, Sudarsanam V: Design, synthesis, and pharmacological evaluation of some 2-[4-morpholino]-3-aryl-5-substituted thiophenes as novel anti-inflammatory agents: generation of a novel anti-inflammatory pharmacophore. Bioorg Med Chem. 2004 Sep 1;12(17):4667-71. [PubMed:15358292 ]
    4. Nieves-Neira W, Rivera MI, Kohlhagen G, Hursey ML, Pourquier P, Sausville EA, Pommier Y: DNA protein cross-links produced by NSC 652287, a novel thiophene derivative active against human renal cancer cells. Mol Pharmacol. 1999 Sep;56(3):478-84. [PubMed:10462535 ]
    5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

    PMID: 21210664