(2R)-N-{4-[Ethyl(phenyl)sulfamoyl]-2-methylphenyl}-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

Identification

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Name
(2R)-N-{4-[Ethyl(phenyl)sulfamoyl]-2-methylphenyl}-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide
Accession Number
DB08609
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 430.441
Monoisotopic: 430.117412475
Chemical Formula
C19H21F3N2O4S
InChI Key
SHEIQJGQDUYUBE-GOSISDBHSA-N
InChI
InChI=1S/C19H21F3N2O4S/c1-4-24(14-8-6-5-7-9-14)29(27,28)15-10-11-16(13(2)12-15)23-17(25)18(3,26)19(20,21)22/h5-12,26H,4H2,1-3H3,(H,23,25)/t18-/m1/s1
IUPAC Name
N-{4-[ethyl(phenyl)sulfamoyl]-2-methylphenyl}-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide
SMILES
[H]N(C(=O)C(C)(O)C(F)(F)F)C1=C(C)C=C(C=C1)S(=O)(=O)N(CC)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 2, mitochondrialNot AvailableHumans
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
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
6102762
PubChem Substance
99445080
ChemSpider
4810270
HET
TF2
PDB Entries
2bu6

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00734 mg/mLALOGPS
logP3.17ALOGPS
logP3.58ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.71 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.05 m3·mol-1ChemAxon
Polarizability40.26 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9928
Blood Brain Barrier+0.6549
Caco-2 permeable-0.5914
P-glycoprotein substrateNon-substrate0.6355
P-glycoprotein inhibitor INon-inhibitor0.6799
P-glycoprotein inhibitor IIInhibitor0.6047
Renal organic cation transporterNon-inhibitor0.9505
CYP450 2C9 substrateNon-substrate0.5755
CYP450 2D6 substrateNon-substrate0.8169
CYP450 3A4 substrateNon-substrate0.5556
CYP450 1A2 substrateNon-inhibitor0.7909
CYP450 2C9 inhibitorInhibitor0.622
CYP450 2D6 inhibitorNon-inhibitor0.8014
CYP450 2C19 inhibitorInhibitor0.6414
CYP450 3A4 inhibitorInhibitor0.6999
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.696
Ames testNon AMES toxic0.689
CarcinogenicityNon-carcinogens0.5138
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3824 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9974
hERG inhibition (predictor II)Non-inhibitor0.7613
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 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 sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Sulfanilides
Direct Parent
Sulfanilides
Alternative Parents
Benzenesulfonamides / Anilides / Benzenesulfonyl compounds / N-arylamides / Toluenes / Organosulfonamides / Tertiary alcohols / Aminosulfonyl compounds / Fluorohydrins / Secondary carboxylic acid amides
show 6 more
Substituents
Benzenesulfonamide / Sulfanilide / Anilide / Benzenesulfonyl group / N-arylamide / Toluene / Organosulfonic acid amide / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Aminosulfonyl compound
show 22 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyruvate dehydrogenase (acetyl-transferring) kinase activity
Specific Function
Kinase that plays a key role in the regulation of glucose and fatty acid metabolism and homeostasis via phosphorylation of the pyruvate dehydrogenase subunits PDHA1 and PDHA2. This inhibits pyruvat...
Gene Name
PDK2
Uniprot ID
Q15119
Uniprot Name
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial
Molecular Weight
46153.39 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 15, 2010 15:33 / Updated on June 04, 2019 07:00