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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:32:14 UTC
Update Date2019-01-11 19:38:41 UTC
HMDB IDHMDB0029718
Secondary Accession Numbers
  • HMDB29718
Metabolite Identification
Common NameThiophene
DescriptionThiophene 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 sulfonation is the basis for the separation of thiophene from benzene, which are difficult 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
Structure
Data?1547235521
Synonyms
ValueSource
ThiofuranChEBI
ThiophenChEBI
2-Thienylacetic acidHMDB
2-Thiopheneacetic acidHMDB
Divinylene sulfideHMDB
Hopkin'S lactic acid reagentHMDB
PolythiopheneHMDB
ThiacyclopentadieneHMDB
ThiapheneHMDB
Thien-2-ylacetateHMDB
thio-FuranHMDB
ThiofenHMDB
ThiofuramHMDB
ThiofurfuranHMDB
ThioleHMDB
Thiophene, homopolymerHMDB
ThiotetroleHMDB
Chemical FormulaC4H4S
Average Molecular Weight84.14
Monoisotopic Molecular Weight84.003370818
IUPAC Namethiophene
Traditional Namethiophene
CAS Registry Number110-02-1
SMILES
S1C=CC=C1
InChI Identifier
InChI=1S/C4H4S/c1-2-4-5-3-1/h1-4H
InChI KeyYTPLMLYBLZKORZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassHeteroaromatic compounds
Sub ClassNot Available
Direct ParentHeteroaromatic compounds
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Thiophene
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-38.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.01 mg/mL at 25 °CNot Available
LogP1.81Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP1.89ALOGPS
logP1.75ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity23.16 m³·mol⁻¹ChemAxon
Polarizability8.56 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-b617a94704f7b42da42dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-c293c7cf614468c6e0e4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-9000000000-9a03d6e6508f83882334JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-052f8b82aca4fcb7d715JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-3b6cb97c53d937e7660aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9000000000-67fd3ae2e7363f5336a5JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-11132.240 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-49401.791 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000912
KNApSAcK IDNot Available
Chemspider ID7739
KEGG Compound IDC02595
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThiophene
METLIN IDNot Available
PubChem Compound8030
PDB IDNot Available
ChEBI ID30856
References
Synthesis ReferenceNot 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.. .