NAV

N-[(1S)-2-{[(1R)-2-(benzyloxy)-1-cyano-1-methylethyl]amino}-1-(cyclohexylmethyl)-2-oxoethyl]morpholine-4-carboxamide

Identification

Generic Name
N-[(1S)-2-{[(1R)-2-(benzyloxy)-1-cyano-1-methylethyl]amino}-1-(cyclohexylmethyl)-2-oxoethyl]morpholine-4-carboxamide
DrugBank Accession Number
DB08755
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 456.5777
Monoisotopic: 456.27365566
Chemical Formula
C25H36N4O4
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 n-carbamoyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an carbamoyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-carbamoyl-alpha amino acids and derivatives
Alternative Parents
Alpha amino acid amides / Morpholine carboxylic acids and derivatives / Benzylethers / Fatty amides / Ureas / Secondary carboxylic acid amides / Oxacyclic compounds / Nitriles / Dialkyl ethers / Azacyclic compounds
show 4 more
Substituents
Alpha-amino acid amide / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzylether / Carbonic acid derivative / Carbonitrile / Carbonyl group / Carboxamide group / Dialkyl ether
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MQWUTQCRGGBPBT-WIOPSUGQSA-N
InChI
InChI=1S/C25H36N4O4/c1-25(18-26,19-33-17-21-10-6-3-7-11-21)28-23(30)22(16-20-8-4-2-5-9-20)27-24(31)29-12-14-32-15-13-29/h3,6-7,10-11,20,22H,2,4-5,8-9,12-17,19H2,1H3,(H,27,31)(H,28,30)/t22-,25+/m0/s1
IUPAC Name
(2S)-N-[(1R)-2-(benzyloxy)-1-cyano-1-methylethyl]-3-cyclohexyl-2-[(morpholine-4-carbonyl)amino]propanamide
SMILES
[H][C@@](CC1CCCCC1)(NC(=O)N1CCOCC1)C(=O)N[C@@](C)(COCC1=CC=CC=C1)C#N

References

General References
Not Available
PubChem Compound
46937176
PubChem Substance
99445226
ChemSpider
25061202
ZINC
ZINC000038970701
PDBe Ligand
Y15
PDB Entries
2r9o

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 Solubility0.03 mg/mLALOGPS
logP2.68ALOGPS
logP2.53Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)11.76Chemaxon
pKa (Strongest Basic)-1.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area103.69 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity125.06 m3·mol-1Chemaxon
Polarizability48.97 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7663
Blood Brain Barrier-0.638
Caco-2 permeable-0.7157
P-glycoprotein substrateSubstrate0.8939
P-glycoprotein inhibitor IInhibitor0.9036
P-glycoprotein inhibitor IINon-inhibitor0.9151
Renal organic cation transporterNon-inhibitor0.8236
CYP450 2C9 substrateNon-substrate0.8276
CYP450 2D6 substrateNon-substrate0.8015
CYP450 3A4 substrateSubstrate0.5363
CYP450 1A2 substrateNon-inhibitor0.9293
CYP450 2C9 inhibitorNon-inhibitor0.7488
CYP450 2D6 inhibitorNon-inhibitor0.9087
CYP450 2C19 inhibitorNon-inhibitor0.6327
CYP450 3A4 inhibitorInhibitor0.7684
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9567
Ames testNon AMES toxic0.7185
CarcinogenicityNon-carcinogens0.8953
BiodegradationNot ready biodegradable0.9765
Rat acute toxicity2.6242 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6978
hERG inhibition (predictor II)Inhibitor0.6251
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/MSsplash10-0a4i-1016900000-13b54e134c79e54a1620
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-24c8d34515025be3fed4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01x0-1296000000-6d528a402fd6579fed53
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1029100000-d64ca3cc92b65d0db48c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00mo-6910100000-43503326d077d3c80c4b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0w91-1390100000-abcb21a30620d44e543a
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]-207.54604
predicted
DeepCCS 1.0 (2019)
[M+H]+209.90404
predicted
DeepCCS 1.0 (2019)
[M+Na]+216.3254
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 21:34 / Updated at June 12, 2020 16:52