NAV

4-({(2R,5S)-2,5-DIMETHYL-4-[(2R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPANOYL]PIPERAZIN-1-YL}CARBONYL)BENZONITRILE

Identification

Generic Name
4-({(2R,5S)-2,5-DIMETHYL-4-[(2R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPANOYL]PIPERAZIN-1-YL}CARBONYL)BENZONITRILE
DrugBank Accession Number
DB08608
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 383.3649
Monoisotopic: 383.145676136
Chemical Formula
C18H20F3N3O3
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 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

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
Benzoyl derivatives / Benzonitriles / Piperazines / Tertiary carboxylic acid amides / Tertiary alcohols / Fluorohydrins / Nitriles / Azacyclic compounds / Organopnictogen compounds / Organofluorides
show 4 more
Substituents
1,4-diazinane / Alcohol / Alkyl fluoride / Alkyl halide / Aromatic heteromonocyclic compound / Azacycle / Benzamide / Benzonitrile / Benzoyl / Carbonitrile
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
IWFSHKKFDSWNLZ-BWACUDIHSA-N
InChI
InChI=1S/C18H20F3N3O3/c1-11-10-24(16(26)17(3,27)18(19,20)21)12(2)9-23(11)15(25)14-6-4-13(8-22)5-7-14/h4-7,11-12,27H,9-10H2,1-3H3/t11-,12+,17-/m1/s1
IUPAC Name
4-[(2R,5S)-2,5-dimethyl-4-[(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]piperazine-1-carbonyl]benzonitrile
SMILES
[H][C@@]1(C)CN(C(=O)[C@@](C)(O)C(F)(F)F)[C@@]([H])(C)CN1C(=O)C1=CC=C(C=C1)C#N

References

General References
Not Available
PubChem Compound
6102761
PubChem Substance
99445079
ChemSpider
4810269
BindingDB
50236533
ChEMBL
CHEMBL316388
ZINC
ZINC000003941524
PDBe Ligand
TF1
PDB Entries
2bu2 / 2bu5

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 Solubility0.0366 mg/mLALOGPS
logP1.82ALOGPS
logP1.82Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)9.55Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area84.64 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity91.42 m3·mol-1Chemaxon
Polarizability36.07 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.988
Blood Brain Barrier+0.8017
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.751
P-glycoprotein inhibitor IInhibitor0.7915
P-glycoprotein inhibitor IIInhibitor0.5181
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8289
CYP450 2D6 substrateNon-substrate0.7989
CYP450 3A4 substrateSubstrate0.634
CYP450 1A2 substrateNon-inhibitor0.8619
CYP450 2C9 inhibitorNon-inhibitor0.7009
CYP450 2D6 inhibitorNon-inhibitor0.9056
CYP450 2C19 inhibitorNon-inhibitor0.5413
CYP450 3A4 inhibitorInhibitor0.6677
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6743
Ames testNon AMES toxic0.7444
CarcinogenicityNon-carcinogens0.7806
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6840 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9957
hERG inhibition (predictor II)Non-inhibitor0.5238
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/MSsplash10-001i-0009000000-d22a5716f62c39850e99
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0109000000-e941c07e85993f1a6cdb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-3943000000-9792670050b3df694961
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0927000000-a61db073c644b59559b0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fl9-0914000000-2b5b9d14a597d4466cdf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0912000000-85a60f61425072fd7115
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]-183.78957
predicted
DeepCCS 1.0 (2019)
[M+H]+186.0209
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.93343
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. [Pyruvate dehydrogenase [lipoamide]] kinase isozyme 2, 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 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. [Article]

Drug created at September 15, 2010 21:33 / Updated at June 12, 2020 16:52