Thenoyltrifluoroacetone
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Identification
- Generic Name
- Thenoyltrifluoroacetone
- DrugBank Accession Number
- DB04795
- Background
Thenoyltrifluoroacetone is a chelating agent and inhibitor of cellular respiration.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 222.184
Monoisotopic: 221.996234709 - Chemical Formula
- C8H5F3O2S
- Synonyms
- 1-Thenoyl-3,3,3-trifluoroacetone
- 1,1,1-Trifluoro-3-(2-thenoyl)acetone
- 2-Thenoyltrifluoroacetone
- alpha-Thenoyltrifluoroacetone
- Perfluoroacetyl(2-thenoyl)methane
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Studies indicate that thenoyltrifluoroacetone is a potent inhibitor of carboxylesterase activity, in addition to its ability to inhibit mitochondrial complex II activity.
- Mechanism of action
Target Actions Organism ULiver carboxylesterase 1 Not Available Humans USuccinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareTechnetium Tc-99m oxidronate Thenoyltrifluoroacetone may decrease effectiveness of Technetium Tc-99m oxidronate as a diagnostic agent. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbonyl compounds
- Direct Parent
- Aryl alkyl ketones
- Alternative Parents
- Beta-diketones / Thiophenes / Heteroaromatic compounds / Alpha-haloketones / Organofluorides / Organic oxides / Hydrocarbon derivatives / Alkyl fluorides
- Substituents
- 1,3-dicarbonyl compound / 1,3-diketone / Alkyl fluoride / Alkyl halide / Alpha-haloketone / Aromatic heteromonocyclic compound / Aryl alkyl ketone / Heteroaromatic compound / Hydrocarbon derivative / Organic oxide
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- MYQ9MNW7NI
- CAS number
- 326-91-0
- InChI Key
- TXBBUSUXYMIVOS-UHFFFAOYSA-N
- InChI
- InChI=1S/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2
- IUPAC Name
- 4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione
- SMILES
- FC(F)(F)C(=O)CC(=O)C1=CC=CS1
References
- General References
- Zhang JG, Fariss MW: Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. Biochem Pharmacol. 2002 Feb 15;63(4):751-4. [Article]
- External Links
- PubChem Compound
- 5601
- PubChem Substance
- 46504456
- ChemSpider
- 5399
- ChEMBL
- CHEMBL1236433
- ZINC
- ZINC000100004957
- PDBe Ligand
- TTF
- Wikipedia
- Thenoyltrifluoroacetone
- PDB Entries
- 1zp0 / 6myp
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 42 °C PhysProp boiling point (°C) 96-98 °C at 8.00E+00 mm Hg PhysProp logP 1.46 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.0752 mg/mL ALOGPS logP 2.37 ALOGPS logP 2.8 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 7.44 Chemaxon pKa (Strongest Basic) -8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 34.14 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 44.26 m3·mol-1 Chemaxon Polarizability 16.74 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9964 Caco-2 permeable + 0.537 P-glycoprotein substrate Non-substrate 0.8104 P-glycoprotein inhibitor I Non-inhibitor 0.7748 P-glycoprotein inhibitor II Non-inhibitor 0.783 Renal organic cation transporter Non-inhibitor 0.8788 CYP450 2C9 substrate Non-substrate 0.8094 CYP450 2D6 substrate Non-substrate 0.8448 CYP450 3A4 substrate Non-substrate 0.7506 CYP450 1A2 substrate Non-inhibitor 0.6133 CYP450 2C9 inhibitor Inhibitor 0.582 CYP450 2D6 inhibitor Non-inhibitor 0.7097 CYP450 2C19 inhibitor Inhibitor 0.7893 CYP450 3A4 inhibitor Non-inhibitor 0.7544 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5302 Ames test Non AMES toxic 0.5586 Carcinogenicity Non-carcinogens 0.6418 Biodegradation Not ready biodegradable 0.8573 Rat acute toxicity 2.7650 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9736 hERG inhibition (predictor II) Non-inhibitor 0.9203
Spectra
- Mass Spec (NIST)
- Download (9.36 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0rkl-9410000000-59524f075ebfb37cde00 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0090000000-bc3df9db938aaddcad48 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0090000000-66889a0e94296130fba5 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0920000000-aa93b8c940c4adc75e29 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0230-8590000000-c562c82b6b7130634980 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0uxr-9710000000-ae5e3af07df4212b55c7 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9100000000-4c93038beb63e7157167 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 143.02664 predictedDeepCCS 1.0 (2019) [M+H]+ 145.42223 predictedDeepCCS 1.0 (2019) [M+Na]+ 151.85776 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsLiver carboxylesterase 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Triglyceride lipase activity
- Specific Function
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
- Gene Name
- CES1
- Uniprot ID
- P23141
- Uniprot Name
- Liver carboxylesterase 1
- Molecular Weight
- 62520.62 Da
References
- Zhang JG, Fariss MW: Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. Biochem Pharmacol. 2002 Feb 15;63(4):751-4. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Succinate dehydrogenase activity
- Specific Function
- Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate ...
- Gene Name
- SDHA
- Uniprot ID
- P31040
- Uniprot Name
- Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
- Molecular Weight
- 72690.975 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52