Ticrynafen (CHEM016907)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:47:16 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016907
Identification
Common NameTicrynafen
ClassSmall Molecule
DescriptionAn aromatic ketone that is 2,3-dichlorophenoxyacetic acid in which the hydrogen at position 4 on the benzene ring is replaced by a thiophenecarbonyl group. A loop diuretic used to treat hypertension, it was withdrawn from the market in 1982 due to links with hepatitis.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic acidChEBI
(2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic acidChEBI
4-(2-Theonyl)-2,3-dichlorphenoxyessigsaeureChEBI
4-(2-Thienylketo)-2,3-dichlorophenoxyacetic acidChEBI
Acide tieniliqueChEBI
Acido tienilicoChEBI
Acidum tienilicumChEBI
Thienylic acidChEBI
TicrynafenChEBI
SelacrynKegg
(2,3-Dichloro-4-(2-thenoyl)phenoxy)acetateGenerator
(2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetateGenerator
4-(2-Thienylketo)-2,3-dichlorophenoxyacetateGenerator
ThienylateGenerator
TienilateGenerator
Acid, thienylicMeSH
Acid, tienilicMeSH
Tienilic acidMeSH
Chemical FormulaC13H8Cl2O4S
Average Molecular Mass331.171 g/mol
Monoisotopic Mass329.952 g/mol
CAS Registry Number40180-04-9
IUPAC Name2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid
Traditional Nameticrynafen
SMILESOC(=O)COC1=C(Cl)C(Cl)=C(C=C1)C(=O)C1=CC=CS1
InChI IdentifierInChI=1S/C13H8Cl2O4S/c14-11-7(13(18)9-2-1-5-20-9)3-4-8(12(11)15)19-6-10(16)17/h1-5H,6H2,(H,16,17)
InChI KeyAGHANLSBXUWXTB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-phenylketones
Alternative Parents
Substituents
  • Aryl-phenylketone
  • Chlorophenoxyacetate
  • Phenoxyacetate
  • Phenoxy compound
  • 1,2-dichlorobenzene
  • Benzoyl
  • Phenol ether
  • Thiophene carboxylic acid or derivatives
  • Alkyl aryl ether
  • Halobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous halide
  • Thiophene
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organochloride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0025 g/LALOGPS
logP4.09ALOGPS
logP3.87ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.68 m³·mol⁻¹ChemAxon
Polarizability30.45 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-6930000000-f63fca8a05df421cff0eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-446d66363ddb92cb2d50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0009000000-a87109fb3d8db700aa54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btc-4292000000-042781873dcaa9ab3909Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-c55afae4bf1556baba73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0039000000-3b7e8adf4b687fe0ead5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9010000000-00db6c72a610b41c8723Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04831
HMDB IDHMDB0259082
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTienilic_acid
Chemspider ID35204
ChEBI ID9590
PubChem Compound IDNot Available
Kegg Compound IDC11702
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22462724
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23013248
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24575896
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2714684
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=41229
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=471149
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=471154
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=504040
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=6996137
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=7004678
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=7074982
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=7128663
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=7398677
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=8823314
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=913063