NAV

Trifluoromethionine

Identification

Generic Name
Trifluoromethionine
DrugBank Accession Number
DB03799
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 203.183
Monoisotopic: 203.02278381
Chemical Formula
C5H8F3NO2S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMethionine--tRNA ligaseNot AvailableEscherichia coli (strain K12)
UMethionine aminopeptidaseNot AvailableEscherichia coli (strain K12)
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
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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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Thia fatty acids / Halogenated fatty acids / Trihalomethanes / Amino acids / Sulfenyl compounds / Monocarboxylic acids and derivatives / Dialkylthioethers / Carboxylic acids / Organopnictogen compounds / Organofluorides
show 5 more
Substituents
Aliphatic acyclic compound / Alkyl fluoride / Alkyl halide / Amine / Amino acid / Carbonyl group / Carboxylic acid / Dialkylthioether / Fatty acid / Fatty acyl
show 20 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organofluorine compound, non-proteinogenic L-alpha-amino acid, L-methionine derivative (CHEBI:43978)
Affected organisms
Not Available

Chemical Identifiers

UNII
QH3U5JK2DR
CAS number
Not Available
InChI Key
YLJLTSVBCXYTQK-VKHMYHEASA-N
InChI
InChI=1S/C5H8F3NO2S/c6-5(7,8)12-2-1-3(9)4(10)11/h3H,1-2,9H2,(H,10,11)/t3-/m0/s1
IUPAC Name
(2S)-2-amino-4-[(trifluoromethyl)sulfanyl]butanoic acid
SMILES
N[C@@H](CCSC(F)(F)F)C(O)=O

References

Synthesis Reference

Norio SHIBATA, Hiroyuki YASUI, "Simple preparation of trifluoromethionine and derivatives thereof." U.S. Patent US20110015433, issued January 20, 2011.

US20110015433
General References
Not Available
PubChem Compound
165196
PubChem Substance
46507751
ChemSpider
144820
ChEBI
43978
ZINC
ZINC000001698833
Therapeutic Targets Database
DNC001467
PDBe Ligand
MF3
PDB Entries
1c22 / 1pfw

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.8 mg/mLALOGPS
logP-1.9ALOGPS
logP-0.85Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.59Chemaxon
pKa (Strongest Basic)9.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area63.32 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity37.81 m3·mol-1Chemaxon
Polarizability15.85 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9814
Blood Brain Barrier+0.9353
Caco-2 permeable-0.6371
P-glycoprotein substrateNon-substrate0.7842
P-glycoprotein inhibitor INon-inhibitor0.9614
P-glycoprotein inhibitor IINon-inhibitor0.9699
Renal organic cation transporterNon-inhibitor0.9263
CYP450 2C9 substrateNon-substrate0.8197
CYP450 2D6 substrateNon-substrate0.7865
CYP450 3A4 substrateNon-substrate0.726
CYP450 1A2 substrateNon-inhibitor0.6821
CYP450 2C9 inhibitorNon-inhibitor0.8807
CYP450 2D6 inhibitorNon-inhibitor0.9262
CYP450 2C19 inhibitorNon-inhibitor0.8591
CYP450 3A4 inhibitorNon-inhibitor0.9136
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9709
Ames testNon AMES toxic0.7609
CarcinogenicityNon-carcinogens0.8574
BiodegradationNot ready biodegradable0.9285
Rat acute toxicity2.4381 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9944
hERG inhibition (predictor II)Non-inhibitor0.9031
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4l-9400000000-41fa4659009e0896d063
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0290000000-49bb6f406227cd35fef3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-42f4f3a80ea7a8f9c1da
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-4910000000-aadf51c9349507927f58
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-986393b8dbad9d262f9d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-8900000000-59d77d30514786eb47b0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-08fr-9500000000-912030f2f12ca9ed9ec5
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.40074
predicted
DeepCCS 1.0 (2019)
[M+H]+139.7733
predicted
DeepCCS 1.0 (2019)
[M+Na]+149.33565
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Methionine--tRNA ligase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Is required not only for elongation of protein synthesis but also for the initiation of all mRNA translation through initiator tRNA(fMet) aminoacylation.
Gene Name
metG
Uniprot ID
P00959
Uniprot Name
Methionine--tRNA ligase
Molecular Weight
76254.1 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details2. Methionine aminopeptidase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Metalloaminopeptidase activity
Specific Function
Removes the N-terminal methionine from nascent proteins. The N-terminal methionine is often cleaved when the second residue in the primary sequence is small and uncharged (Met-Ala-, Cys, Gly, Pro, ...
Gene Name
map
Uniprot ID
P0AE18
Uniprot Name
Methionine aminopeptidase
Molecular Weight
29330.585 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52