Thenoyltrifluoroacetone

Identification

Name
Thenoyltrifluoroacetone
Accession Number
DB04795
Type
Small Molecule
Groups
Experimental
Description

Thenoyltrifluoroacetone is a chelating agent and inhibitor of cellular respiration. [PubChem]

Structure
Thumb
Synonyms
  • .alpha.-Thenoyltrifluoroacetone
  • 1-Thenoyl-3,3,3-trifluoroacetone
  • 1,1,1-Trifluoro-3-(2-thenoyl)acetone
  • 2-Thenoyltrifluoroacetone
  • alpha-Thenoyltrifluoroacetone
  • Perfluoroacetyl(2-thenoyl)methane
  • TTFA
Categories
UNII
MYQ9MNW7NI
CAS number
326-91-0
Weight
Average: 222.184
Monoisotopic: 221.996234709
Chemical Formula
C8H5F3O2S
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
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
TargetActionsOrganism
ULiver carboxylesterase 1Not AvailableHuman
USuccinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrialNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Zhang JG, Fariss MW: Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. Biochem Pharmacol. 2002 Feb 15;63(4):751-4. [PubMed:11992644]
External Links
PubChem Compound
5601
PubChem Substance
46504456
ChemSpider
5399
HET
TTF
PDB Entries
1zp0

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)42 °CPhysProp
boiling point (°C)96-98 °C at 8.00E+00 mm HgPhysProp
logP1.46HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0752 mg/mLALOGPS
logP2.37ALOGPS
logP2.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.17ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.26 m3·mol-1ChemAxon
Polarizability16.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9964
Caco-2 permeable+0.537
P-glycoprotein substrateNon-substrate0.8104
P-glycoprotein inhibitor INon-inhibitor0.7748
P-glycoprotein inhibitor IINon-inhibitor0.783
Renal organic cation transporterNon-inhibitor0.8788
CYP450 2C9 substrateNon-substrate0.8094
CYP450 2D6 substrateNon-substrate0.8448
CYP450 3A4 substrateNon-substrate0.7506
CYP450 1A2 substrateNon-inhibitor0.6133
CYP450 2C9 inhibitorInhibitor0.582
CYP450 2D6 inhibitorNon-inhibitor0.7097
CYP450 2C19 inhibitorInhibitor0.7893
CYP450 3A4 inhibitorNon-inhibitor0.7544
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5302
Ames testNon AMES toxic0.5586
CarcinogenicityNon-carcinogens0.6418
BiodegradationNot ready biodegradable0.8573
Rat acute toxicity2.7650 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9736
hERG inhibition (predictor II)Non-inhibitor0.9203
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.36 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Aryl alkyl ketone / 1,3-diketone / 1,3-dicarbonyl compound / Alpha-haloketone / Heteroaromatic compound / Thiophene / Organoheterocyclic compound / Organic oxide / Hydrocarbon derivative / Organofluoride
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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
  1. Zhang JG, Fariss MW: Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. Biochem Pharmacol. 2002 Feb 15;63(4):751-4. [PubMed:11992644]
  2. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10592235]

Drug created on September 11, 2007 11:49 / Updated on October 02, 2017 05:38