You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:46:44 UTC
Update Date2019-07-23 06:26:41 UTC
HMDB IDHMDB0038459
Secondary Accession Numbers
  • HMDB38459
Metabolite Identification
Common Name5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene
Description5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene, also known as triptolid or TPL, 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. 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863201
Synonyms
ValueSource
TPLHMDB
TriptolidHMDB
TriptolideHMDB
Triptolide (9ci)HMDB
Triptolide, tripterygium wilfordiiHMDB
4-{[2,2'-bithiophene]-5-yl}-2-oxobut-3-yn-1-yl acetic acidGenerator
Chemical FormulaC14H10O3S2
Average Molecular Weight290.357
Monoisotopic Molecular Weight290.007135566
IUPAC Name2-oxo-4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate
Traditional Name2-oxo-4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate
CAS Registry Number1222-83-9
SMILES
CC(=O)OCC(=O)C#CC1=CC=C(S1)C1=CC=CS1
InChI Identifier
InChI=1S/C14H10O3S2/c1-10(15)17-9-11(16)4-5-12-6-7-14(19-12)13-3-2-8-18-13/h2-3,6-8H,9H2,1H3
InChI KeyDTTMMEKKOHDZHY-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
  • Alpha-acyloxy ketone
  • Thiophene
  • Alpha,beta-unsaturated ketone
  • Heteroaromatic compound
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point68 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.35ALOGPS
logP3.44ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)17.1ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.55 m³·mol⁻¹ChemAxon
Polarizability30.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-6390000000-a703e07ce2d493a7135aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0090000000-9f1d31b78d9dfae649cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-1190000000-33a952358358fc1a70ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-7390000000-8f5c11eb1f9d42ae34dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2090000000-6ab1c097b48779266178Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-4190000000-4614b7d2689a676cd581Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9110000000-522751047a26b6cd87feSpectrum
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 IDFDB017818
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752377
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .