N-(1-CYANOCYCLOPROPYL)-3-({[(2S)-5-OXOPYRROLIDIN-2-YL]METHYL}SULFONYL)-N~2~-[(1S)-2,2,2-TRIFLUORO-1-(4-FLUOROPHENYL)ETHYL]-L-ALANINAMIDE
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Identification
- Generic Name
- N-(1-CYANOCYCLOPROPYL)-3-({[(2S)-5-OXOPYRROLIDIN-2-YL]METHYL}SULFONYL)-N~2~-[(1S)-2,2,2-TRIFLUORO-1-(4-FLUOROPHENYL)ETHYL]-L-ALANINAMIDE
- DrugBank Accession Number
- DB07587
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 490.472
Monoisotopic: 490.129788722 - Chemical Formula
- C20H22F4N4O4S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UCathepsin S 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 alpha amino acid amides. These are amide derivatives of alpha amino acids.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acid amides
- Alternative Parents
- Aralkylamines / Fluorobenzenes / Pyrrolidine-2-ones / Aryl fluorides / Sulfones / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Nitriles / Dialkylamines show 6 more
- Substituents
- 2-pyrrolidone / Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle show 27 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- sulfone, nitrile, pyrrolidin-2-ones, L-alanine derivative, monofluorobenzenes, carbocyclic compound (CHEBI:41677)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- JLPXDVXMMYRTKN-ZOBUZTSGSA-N
- InChI
- InChI=1S/C20H22F4N4O4S/c21-13-3-1-12(2-4-13)17(20(22,23)24)27-15(18(30)28-19(11-25)7-8-19)10-33(31,32)9-14-5-6-16(29)26-14/h1-4,14-15,17,27H,5-10H2,(H,26,29)(H,28,30)/t14-,15-,17-/m0/s1
- IUPAC Name
- (2R)-N-(1-cyanocyclopropyl)-3-{[(2S)-5-oxopyrrolidin-2-yl]methanesulfonyl}-2-{[(1S)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl]amino}propanamide
- SMILES
- [H][C@@](CS(=O)(=O)C[C@]1([H])CCC(=O)N1)(N[C@@]([H])(C1=CC=C(F)C=C1)C(F)(F)F)C(=O)NC1(CC1)C#N
References
- General References
- Not Available
- External Links
- PubChem Compound
- 11840933
- PubChem Substance
- 99444058
- ChemSpider
- 10015438
- ZINC
- ZINC000036470913
- PDBe Ligand
- CRJ
- PDB Entries
- 2fq9
Clinical Trials
- Clinical Trials
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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 0.21 mg/mL ALOGPS logP 1.49 ALOGPS logP 0.17 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 10.66 Chemaxon pKa (Strongest Basic) 1.74 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 128.16 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 107.04 m3·mol-1 Chemaxon Polarizability 42.56 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9422 Blood Brain Barrier + 0.8257 Caco-2 permeable - 0.6525 P-glycoprotein substrate Substrate 0.6057 P-glycoprotein inhibitor I Non-inhibitor 0.6138 P-glycoprotein inhibitor II Non-inhibitor 0.9897 Renal organic cation transporter Non-inhibitor 0.8833 CYP450 2C9 substrate Non-substrate 0.8049 CYP450 2D6 substrate Non-substrate 0.8 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.821 CYP450 2C9 inhibitor Non-inhibitor 0.7532 CYP450 2D6 inhibitor Non-inhibitor 0.8639 CYP450 2C19 inhibitor Non-inhibitor 0.6617 CYP450 3A4 inhibitor Inhibitor 0.6601 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8822 Ames test Non AMES toxic 0.6143 Carcinogenicity Non-carcinogens 0.8073 Biodegradation Not ready biodegradable 0.9962 Rat acute toxicity 2.5651 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7731 hERG inhibition (predictor II) Non-inhibitor 0.5715
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0000900000-4d94215575510c3ed6ac Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00kr-0000900000-4ae83e9e47a673795544 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-4000900000-f8826ab7e830514df0e9 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0avr-1010900000-4fc7a4ebe88c9cabad8d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0gj0-9601700000-7d3d9d1d37b7d260357d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-2290100000-56c2168a14c166cc51ff 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]- 194.85164 predictedDeepCCS 1.0 (2019) [M+H]+ 196.67653 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.28235 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsCathepsin S
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Thiol protease. Key protease responsible for the removal of the invariant chain from MHC class II molecules and MHC class II antigen presentation (PubMed:30612035). The bond-specificity of this proteinase is in part similar to the specificities of cathepsin L
- Specific Function
- collagen binding
- Gene Name
- CTSS
- Uniprot ID
- P25774
- Uniprot Name
- Cathepsin S
- Molecular Weight
- 37495.49 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 21:23 / Updated at June 12, 2020 16:52