NAV

4-[(3-CHLORO-4-{[(2R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPANOYL]AMINO}PHENYL)SULFONYL]-N,N-DIMETHYLBENZAMIDE

Identification

Generic Name
4-[(3-CHLORO-4-{[(2R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPANOYL]AMINO}PHENYL)SULFONYL]-N,N-DIMETHYLBENZAMIDE
DrugBank Accession Number
DB07403
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 478.87
Monoisotopic: 478.057704708
Chemical Formula
C19H18ClF3N2O5S
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
U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 1, 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

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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzamides
Alternative Parents
Anilides / Benzenesulfonyl compounds / Benzoyl derivatives / N-arylamides / Chlorobenzenes / Aryl chlorides / Tertiary carboxylic acid amides / Tertiary alcohols / Sulfones / Fluorohydrins
show 8 more
Substituents
Alcohol / Alkyl fluoride / Alkyl halide / Anilide / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Benzamide / Benzenesulfonyl group / Benzoyl
show 24 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DTDZLJHKVNTQGZ-GOSISDBHSA-N
InChI
InChI=1S/C19H18ClF3N2O5S/c1-18(28,19(21,22)23)17(27)24-15-9-8-13(10-14(15)20)31(29,30)12-6-4-11(5-7-12)16(26)25(2)3/h4-10,28H,1-3H3,(H,24,27)/t18-/m1/s1
IUPAC Name
4-{3-chloro-4-[(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamido]benzenesulfonyl}-N,N-dimethylbenzamide
SMILES
CN(C)C(=O)C1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1

References

General References
Not Available
PubChem Compound
16741245
PubChem Substance
99443874
ChemSpider
20572552
BindingDB
50236535
ChEMBL
CHEMBL1231132
ZINC
ZINC000001547088
PDBe Ligand
AZX
PDB Entries
2q8g

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 Solubility0.00392 mg/mLALOGPS
logP2.48ALOGPS
logP2.85Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)9.44Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area103.78 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity109.74 m3·mol-1Chemaxon
Polarizability42.55 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8847
Blood Brain Barrier+0.6641
Caco-2 permeable-0.5701
P-glycoprotein substrateNon-substrate0.6251
P-glycoprotein inhibitor INon-inhibitor0.7204
P-glycoprotein inhibitor IINon-inhibitor0.852
Renal organic cation transporterNon-inhibitor0.9488
CYP450 2C9 substrateNon-substrate0.6184
CYP450 2D6 substrateNon-substrate0.8024
CYP450 3A4 substrateSubstrate0.5426
CYP450 1A2 substrateNon-inhibitor0.6945
CYP450 2C9 inhibitorNon-inhibitor0.5701
CYP450 2D6 inhibitorNon-inhibitor0.8719
CYP450 2C19 inhibitorInhibitor0.5471
CYP450 3A4 inhibitorInhibitor0.5841
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7408
Ames testNon AMES toxic0.7149
CarcinogenicityCarcinogens 0.5991
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4658 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9954
hERG inhibition (predictor II)Non-inhibitor0.6522
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/MSsplash10-004i-0000900000-8d9e92215e4e72fbdfc9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-0600900000-475524e3c2786735ac09
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-7900300000-df51e669af8a7a23d590
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-b777e20337ecbdf7f1a6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9046000000-0d19de6805ce0f2d4783
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ce9-1808900000-e75998a5104775c3f6ad
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]-197.64606
predicted
DeepCCS 1.0 (2019)
[M+H]+200.04163
predicted
DeepCCS 1.0 (2019)
[M+Na]+206.43791
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. [Pyruvate dehydrogenase [lipoamide]] kinase isozyme 1, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyruvate dehydrogenase (acetyl-transferring) kinase activity
Specific Function
Kinase that plays a key role in regulation of glucose and fatty acid metabolism and homeostasis via phosphorylation of the pyruvate dehydrogenase subunits PDHA1 and PDHA2. This inhibits pyruvate de...
Gene Name
PDK1
Uniprot ID
Q15118
Uniprot Name
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial
Molecular Weight
49243.765 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. [Article]

Drug created at September 15, 2010 21:21 / Updated at June 12, 2020 16:52