NAV

(1R)-2-[(CYANOMETHYL)AMINO]-1-({[2-(DIFLUOROMETHOXY)BENZYL]SULFONYL}METHYL)-2-OXOETHYL MORPHOLINE-4-CARBOXYLATE

Identification

Generic Name
(1R)-2-[(CYANOMETHYL)AMINO]-1-({[2-(DIFLUOROMETHOXY)BENZYL]SULFONYL}METHYL)-2-OXOETHYL MORPHOLINE-4-CARBOXYLATE
DrugBank Accession Number
DB08195
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 461.437
Monoisotopic: 461.106827141
Chemical Formula
C18H21F2N3O7S
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 morpholine carboxylic acids. These are heterocyclic compounds containing a morpholine ring substituted by one or more carboxylic acid groups.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Oxazinanes
Sub Class
Morpholines
Direct Parent
Morpholine carboxylic acids
Alternative Parents
Phenoxy compounds / Phenol ethers / Sulfones / Carbamate esters / Secondary carboxylic acid amides / Organic carbonic acids and derivatives / Azacyclic compounds / Oxacyclic compounds / Dialkyl ethers / Nitriles
show 6 more
Substituents
Alkyl fluoride / Alkyl halide / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbamic acid ester / Carbonic acid derivative / Carbonitrile / Carbonyl group / Carboxamide group
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, carbamate ester, monocarboxylic acid amide, nitrile, morpholines (CHEBI:44189)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
YKWHKILAGONYKL-HNNXBMFYSA-N
InChI
InChI=1S/C18H21F2N3O7S/c19-17(20)29-14-4-2-1-3-13(14)11-31(26,27)12-15(16(24)22-6-5-21)30-18(25)23-7-9-28-10-8-23/h1-4,15,17H,6-12H2,(H,22,24)/t15-/m0/s1
IUPAC Name
(1R)-1-[(cyanomethyl)carbamoyl]-2-{[2-(difluoromethoxy)phenyl]methanesulfonyl}ethyl morpholine-4-carboxylate
SMILES
[H][C@@](CS(=O)(=O)CC1=C(OC(F)F)C=CC=C1)(OC(=O)N1CCOCC1)C(=O)NCC#N

References

General References
Not Available
PubChem Compound
9547943
PubChem Substance
99444666
ChemSpider
7826878
ZINC
ZINC000024804779
PDBe Ligand
MO9
PDB Entries
2g7y

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 Solubility0.32 mg/mLALOGPS
logP0.95ALOGPS
logP-0.21Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.21Chemaxon
pKa (Strongest Basic)-4.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area135.03 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity101.64 m3·mol-1Chemaxon
Polarizability40.88 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.983
Blood Brain Barrier+0.9435
Caco-2 permeable-0.6187
P-glycoprotein substrateSubstrate0.5364
P-glycoprotein inhibitor IInhibitor0.8223
P-glycoprotein inhibitor IINon-inhibitor0.8222
Renal organic cation transporterNon-inhibitor0.7865
CYP450 2C9 substrateNon-substrate0.8449
CYP450 2D6 substrateNon-substrate0.7998
CYP450 3A4 substrateSubstrate0.5537
CYP450 1A2 substrateNon-inhibitor0.6658
CYP450 2C9 inhibitorNon-inhibitor0.6627
CYP450 2D6 inhibitorNon-inhibitor0.8407
CYP450 2C19 inhibitorInhibitor0.5437
CYP450 3A4 inhibitorNon-inhibitor0.5963
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5386
Ames testNon AMES toxic0.5674
CarcinogenicityNon-carcinogens0.7672
BiodegradationNot ready biodegradable0.9913
Rat acute toxicity2.6106 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8696
hERG inhibition (predictor II)Inhibitor0.776
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/MSsplash10-03di-4101900000-fa8531c4bf09a1f9c249
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-0004900000-6f25c1ffbb21020b7108
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-6953200000-42fbc88c74804a37aee6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fu-1198100000-70eb45b62a313b7b1a2f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01rf-9516500000-bd8c6f13cc79bcd7b070
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-3591100000-553d95092590c561ae18
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]-186.6923
predicted
DeepCCS 1.0 (2019)
[M+H]+189.08788
predicted
DeepCCS 1.0 (2019)
[M+Na]+195.74
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 21:29 / Updated at June 12, 2020 16:52