NAV

N-[1-(AMINOMETHYL)CYCLOPROPYL]-3-(BENZYLSULFONYL)-N~2~-[(1S)-2,2,2-TRIFLUORO-1-(4-HYDROXYPHENYL)ETHYL]-L-ALANINAMIDE

Identification

Generic Name
N-[1-(AMINOMETHYL)CYCLOPROPYL]-3-(BENZYLSULFONYL)-N~2~-[(1S)-2,2,2-TRIFLUORO-1-(4-HYDROXYPHENYL)ETHYL]-L-ALANINAMIDE
DrugBank Accession Number
DB07589
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 485.52
Monoisotopic: 485.15961164
Chemical Formula
C22H26F3N3O4S
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
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 / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Sulfones / Secondary carboxylic acid amides / Dialkylamines / Organopnictogen compounds / Organofluorides / Organic oxides / Monoalkylamines
show 3 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Amine / Aralkylamine / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DWWVPKCSDHDILN-OALUTQOASA-N
InChI
InChI=1S/C22H26F3N3O4S/c23-22(24,25)19(16-6-8-17(29)9-7-16)27-18(20(30)28-21(14-26)10-11-21)13-33(31,32)12-15-4-2-1-3-5-15/h1-9,18-19,27,29H,10-14,26H2,(H,28,30)/t18-,19-/m0/s1
IUPAC Name
(2R)-N-[1-(aminomethyl)cyclopropyl]-3-phenylmethanesulfonyl-2-{[(1S)-2,2,2-trifluoro-1-(4-hydroxyphenyl)ethyl]amino}propanamide
SMILES
[H][C@@](CS(=O)(=O)CC1=CC=CC=C1)(N[C@@]([H])(C1=CC=C(O)C=C1)C(F)(F)F)C(=O)NC1(CN)CC1

References

General References
Not Available
PubChem Compound
11840934
PubChem Substance
99444060
ChemSpider
10015439
ZINC
ZINC000016052050
PDBe Ligand
CRV
PDB Entries
2fra

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 Solubility0.0944 mg/mLALOGPS
logP2.32ALOGPS
logP1.01Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.65Chemaxon
pKa (Strongest Basic)8.99Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area121.52 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity116.6 m3·mol-1Chemaxon
Polarizability45.69 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9787
Blood Brain Barrier+0.6886
Caco-2 permeable-0.6575
P-glycoprotein substrateSubstrate0.6992
P-glycoprotein inhibitor INon-inhibitor0.7314
P-glycoprotein inhibitor IINon-inhibitor0.9817
Renal organic cation transporterNon-inhibitor0.9076
CYP450 2C9 substrateNon-substrate0.7356
CYP450 2D6 substrateNon-substrate0.7886
CYP450 3A4 substrateNon-substrate0.5229
CYP450 1A2 substrateNon-inhibitor0.7852
CYP450 2C9 inhibitorNon-inhibitor0.7191
CYP450 2D6 inhibitorNon-inhibitor0.8247
CYP450 2C19 inhibitorNon-inhibitor0.6526
CYP450 3A4 inhibitorInhibitor0.5532
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7326
Ames testNon AMES toxic0.6231
CarcinogenicityNon-carcinogens0.6562
BiodegradationNot ready biodegradable0.9892
Rat acute toxicity2.4571 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9402
hERG inhibition (predictor II)Inhibitor0.6132
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/MSsplash10-000i-0000900000-7154d209f578e4255fc8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0000900000-bf341c837bb6927671b2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-3003900000-1e5e475401794e45f23a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kai-0033900000-45563797c08acab4dcd6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-9302500000-3b4ae7ab06738a11545f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xv-4890100000-9db8cafe5fcbd18b0e77
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]-201.52214
predicted
DeepCCS 1.0 (2019)
[M+H]+203.4807
predicted
DeepCCS 1.0 (2019)
[M+Na]+209.39323
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cathepsin S
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Proteoglycan binding
Specific Function
Thiol protease. Key protease responsible for the removal of the invariant chain from MHC class II molecules. The bond-specificity of this proteinase is in part similar to the specificities of cathe...
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