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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
3D
Similar Structures
Weight
Average: 490.472
Monoisotopic: 490.129788722
Chemical Formula
C20H22F4N4O4S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCathepsin SNot 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 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
PubChem Compound
11840933
PubChem Substance
99444058
ChemSpider
10015438
ZINC
ZINC000036470913
PDBe Ligand
CRJ
PDB Entries
2fq9

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
PropertyValueSource
Water Solubility0.21 mg/mLALOGPS
logP1.49ALOGPS
logP0.17Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.66Chemaxon
pKa (Strongest Basic)1.74Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area128.16 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity107.04 m3·mol-1Chemaxon
Polarizability42.56 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9422
Blood Brain Barrier+0.8257
Caco-2 permeable-0.6525
P-glycoprotein substrateSubstrate0.6057
P-glycoprotein inhibitor INon-inhibitor0.6138
P-glycoprotein inhibitor IINon-inhibitor0.9897
Renal organic cation transporterNon-inhibitor0.8833
CYP450 2C9 substrateNon-substrate0.8049
CYP450 2D6 substrateNon-substrate0.8
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.821
CYP450 2C9 inhibitorNon-inhibitor0.7532
CYP450 2D6 inhibitorNon-inhibitor0.8639
CYP450 2C19 inhibitorNon-inhibitor0.6617
CYP450 3A4 inhibitorInhibitor0.6601
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8822
Ames testNon AMES toxic0.6143
CarcinogenicityNon-carcinogens0.8073
BiodegradationNot ready biodegradable0.9962
Rat acute toxicity2.5651 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7731
hERG inhibition (predictor II)Non-inhibitor0.5715
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/MSsplash10-0006-0000900000-4d94215575510c3ed6ac
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-0000900000-4ae83e9e47a673795544
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-4000900000-f8826ab7e830514df0e9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0avr-1010900000-4fc7a4ebe88c9cabad8d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gj0-9601700000-7d3d9d1d37b7d260357d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2290100000-56c2168a14c166cc51ff
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]-194.85164
predicted
DeepCCS 1.0 (2019)
[M+H]+196.67653
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.28235
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cathepsin 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
  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 21:23 / Updated at June 12, 2020 16:52