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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:17:52 UTC
Update Date2022-03-07 02:54:06 UTC
HMDB IDHMDB0034454
Secondary Accession Numbers
  • HMDB34454
Metabolite Identification
Common Name5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene
Description5-(4-Acetoxy-1-butynyl)-2,2'-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, 5-(4-acetoxy-1-butynyl)-2,2'-bithiophene is considered to be an oxygenated hydrocarbon. 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene has been detected, but not quantified in, herbs and spices. This could make 5-(4-acetoxy-1-butynyl)-2,2'-bithiophene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene.
Structure
Data?1563862566
Synonyms
ValueSource
4-(5-(2-Thienyl)-2-thienyl)-3-butyn-1-ol acetateChEBI
4-(5-(2-Thienyl)-2-thienyl)-3-butyn-1-ol acetic acidGenerator
3-Butyn-1-ol, 4-(5-(2-thienyl)-2-thienyl)-, acetateHMDB
4-(2,2'-Bithien-5-yl)but-3-yn-1-yl acetateHMDB
5-(4-Acetoxybut-1-ynyl)-2,2'-bithiopheneHMDB
5-(4-Acetoxybut-1-ynyl)-2-2'-bithiopheneHMDB
5-4-ACETOXYBUT-1-ynyl-2-2-bithiopheneHMDB
4-([2,2'-Bithiophen]-5-yl)but-3-yn-1-yl acetic acidGenerator
Chemical FormulaC14H12O2S2
Average Molecular Weight276.374
Monoisotopic Molecular Weight276.027871008
IUPAC Name4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate
Traditional Name4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate
CAS Registry Number1219-28-9
SMILES
CC(=O)OCCC#CC1=CC=C(S1)C1=CC=CS1
InChI Identifier
InChI=1S/C14H12O2S2/c1-11(15)16-9-3-2-5-12-7-8-14(18-12)13-6-4-10-17-13/h4,6-8,10H,3,9H2,1H3
InChI KeyKHPAKGUGOFYJNA-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
  • 2,5-disubstituted thiophene
  • Heteroaromatic compound
  • Thiophene
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP4.61ALOGPS
logP3.74ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.11 m³·mol⁻¹ChemAxon
Polarizability30.13 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.34931661259
DarkChem[M-H]-160.70231661259
DeepCCS[M+H]+152.39530932474
DeepCCS[M-H]-150.01230932474
DeepCCS[M-2H]-184.02130932474
DeepCCS[M+Na]+158.77430932474
AllCCS[M+H]+159.932859911
AllCCS[M+H-H2O]+156.332859911
AllCCS[M+NH4]+163.332859911
AllCCS[M+Na]+164.332859911
AllCCS[M-H]-161.732859911
AllCCS[M+Na-2H]-161.532859911
AllCCS[M+HCOO]-161.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-(4-Acetoxy-1-butynyl)-2,2'-bithiopheneCC(=O)OCCC#CC1=CC=C(S1)C1=CC=CS13234.6Standard polar33892256
5-(4-Acetoxy-1-butynyl)-2,2'-bithiopheneCC(=O)OCCC#CC1=CC=C(S1)C1=CC=CS12336.6Standard non polar33892256
5-(4-Acetoxy-1-butynyl)-2,2'-bithiopheneCC(=O)OCCC#CC1=CC=C(S1)C1=CC=CS12405.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9230000000-554b2fbe8c3c6cedd8bd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-(4-Acetoxy-1-butynyl)-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 - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 10V, Positive-QTOFsplash10-00or-1090000000-cdc8c3dbbc7d5b9171292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 20V, Positive-QTOFsplash10-014i-3690000000-83993ad838519da6972b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 40V, Positive-QTOFsplash10-00l6-9520000000-b3a5619ce781b4bfb35b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 10V, Negative-QTOFsplash10-004i-4190000000-ce9b14e688d25f54633b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 20V, Negative-QTOFsplash10-0a4i-9130000000-50b68e71c9ad3db4f15b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 40V, Negative-QTOFsplash10-0a4l-9200000000-b8979ecd0ba33b4f511f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 10V, Positive-QTOFsplash10-00or-0090000000-72e87881f01aad83c6362021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 20V, Positive-QTOFsplash10-001i-0090000000-460a71401789276498a72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 40V, Positive-QTOFsplash10-0f77-0930000000-2afc7e22a584cd5e504c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 10V, Negative-QTOFsplash10-004i-1090000000-5993b5eb3c52930c57d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 20V, Negative-QTOFsplash10-0udi-0090000000-b80b91c07d0f1b7f348c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 40V, Negative-QTOFsplash10-0udi-1590000000-3573fc31cccca9dd55572021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012863
KNApSAcK IDNot Available
Chemspider ID389319
KEGG Compound IDC04485
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440356
PDB IDNot Available
ChEBI ID17181
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1842961
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .