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N-[1-(AMINOMETHYL)CYCLOPROPYL]-3-(MORPHOLIN-4-YLSULFONYL)-N~2~-[(1S)-2,2,2-TRIFLUORO-1-(4-FLUOROPHENYL)ETHYL]-L-ALANINAMIDE

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Identification

Generic Name
N-[1-(AMINOMETHYL)CYCLOPROPYL]-3-(MORPHOLIN-4-YLSULFONYL)-N~2~-[(1S)-2,2,2-TRIFLUORO-1-(4-FLUOROPHENYL)ETHYL]-L-ALANINAMIDE
DrugBank Accession Number
DB07520
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 482.493
Monoisotopic: 482.16108885
Chemical Formula
C19H26F4N4O4S
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 / Organosulfonamides / Aryl fluorides / Organic sulfonamides / Morpholines / Sulfonyls / Secondary carboxylic acid amides / Oxacyclic compounds / Azacyclic compounds
show 9 more
Substituents
Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 31 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, monocarboxylic acid amide, sulfonamide, morpholines (CHEBI:41259)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
BJIKKEHGGYGGIX-HOTGVXAUSA-N
InChI
InChI=1S/C19H26F4N4O4S/c20-14-3-1-13(2-4-14)16(19(21,22)23)25-15(17(28)26-18(12-24)5-6-18)11-32(29,30)27-7-9-31-10-8-27/h1-4,15-16,25H,5-12,24H2,(H,26,28)/t15-,16-/m0/s1
IUPAC Name
(2R)-N-[1-(aminomethyl)cyclopropyl]-3-(morpholine-4-sulfonyl)-2-{[(1S)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl]amino}propanamide
SMILES
[H][C@@](CS(=O)(=O)N1CCOCC1)(N[C@@]([H])(C1=CC=C(F)C=C1)C(F)(F)F)C(=O)NC1(CN)CC1

References

General References
Not Available
PubChem Compound
11840930
PubChem Substance
99443991
ChemSpider
10015435
ZINC
ZINC000016052054
PDBe Ligand
C28
PDB Entries
2ft2

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 Solubility0.569 mg/mLALOGPS
logP0.8ALOGPS
logP0.062Chemaxon
logS-2.9ALOGPS
pKa (Strongest Acidic)12.94Chemaxon
pKa (Strongest Basic)9.22Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area113.76 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity107.33 m3·mol-1Chemaxon
Polarizability42.97 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9623
Blood Brain Barrier+0.7676
Caco-2 permeable-0.6763
P-glycoprotein substrateSubstrate0.705
P-glycoprotein inhibitor IInhibitor0.6547
P-glycoprotein inhibitor IINon-inhibitor0.9902
Renal organic cation transporterNon-inhibitor0.8813
CYP450 2C9 substrateNon-substrate0.7778
CYP450 2D6 substrateNon-substrate0.7999
CYP450 3A4 substrateNon-substrate0.533
CYP450 1A2 substrateNon-inhibitor0.8711
CYP450 2C9 inhibitorNon-inhibitor0.6402
CYP450 2D6 inhibitorNon-inhibitor0.72
CYP450 2C19 inhibitorNon-inhibitor0.6308
CYP450 3A4 inhibitorInhibitor0.6659
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8627
Ames testNon AMES toxic0.5898
CarcinogenicityNon-carcinogens0.8031
BiodegradationNot ready biodegradable0.9812
Rat acute toxicity2.5780 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9281
hERG inhibition (predictor II)Inhibitor0.6153
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-0000900000-16bcf171e45bc8bc88e1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-0000900000-e806777f244fc2dfa0a8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-1006900000-9d3f8d61a8ae1e02a682
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gx0-2324900000-b2fc716a367064adccc7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05i0-4941700000-6289aa761dd2d65d7cba
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0400-9651800000-123c5f684b827aad3b1e
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]-202.19597
predicted
DeepCCS 1.0 (2019)
[M+H]+204.59154
predicted
DeepCCS 1.0 (2019)
[M+Na]+210.50421
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