4-({(2R,5S)-2,5-DIMETHYL-4-[(2R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPANOYL]PIPERAZIN-1-YL}CARBONYL)BENZONITRILE
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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
- Weight
- Average: 383.3649
Monoisotopic: 383.145676136 - Chemical Formula
- C18H20F3N3O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 2, mitochondrial Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- PubChem Compound
- 6102761
- PubChem Substance
- 99445079
- ChemSpider
- 4810269
- BindingDB
- 50236533
- ChEMBL
- CHEMBL316388
- ZINC
- ZINC000003941524
- PDBe Ligand
- TF1
- PDB Entries
- 2bu2 / 2bu5
Clinical Trials
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
Property Value Source Water Solubility 0.0366 mg/mL ALOGPS logP 1.82 ALOGPS logP 1.82 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 9.55 Chemaxon pKa (Strongest Basic) -1.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 84.64 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 91.42 m3·mol-1 Chemaxon Polarizability 36.07 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.988 Blood Brain Barrier + 0.8017 Caco-2 permeable + 0.5 P-glycoprotein substrate Substrate 0.751 P-glycoprotein inhibitor I Inhibitor 0.7915 P-glycoprotein inhibitor II Inhibitor 0.5181 Renal organic cation transporter Non-inhibitor 0.8178 CYP450 2C9 substrate Non-substrate 0.8289 CYP450 2D6 substrate Non-substrate 0.7989 CYP450 3A4 substrate Substrate 0.634 CYP450 1A2 substrate Non-inhibitor 0.8619 CYP450 2C9 inhibitor Non-inhibitor 0.7009 CYP450 2D6 inhibitor Non-inhibitor 0.9056 CYP450 2C19 inhibitor Non-inhibitor 0.5413 CYP450 3A4 inhibitor Inhibitor 0.6677 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6743 Ames test Non AMES toxic 0.7444 Carcinogenicity Non-carcinogens 0.7806 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6840 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9957 hERG inhibition (predictor II) Non-inhibitor 0.5238
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0009000000-d22a5716f62c39850e99 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0109000000-e941c07e85993f1a6cdb Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03dl-3943000000-9792670050b3df694961 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0927000000-a61db073c644b59559b0 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0fl9-0914000000-2b5b9d14a597d4466cdf Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0912000000-85a60f61425072fd7115 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.78957 predictedDeepCCS 1.0 (2019) [M+H]+ 186.0209 predictedDeepCCS 1.0 (2019) [M+Na]+ 191.93343 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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