NAV

Morpholine-4-Carboxylic Acid [1s-(2-Benzyloxy-1r-Cyano-Ethylcarbamoyl)-3-Methyl-Butyl]Amide

Identification

Generic Name
Morpholine-4-Carboxylic Acid [1s-(2-Benzyloxy-1r-Cyano-Ethylcarbamoyl)-3-Methyl-Butyl]Amide
DrugBank Accession Number
DB03767
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 402.4873
Monoisotopic: 402.226705468
Chemical Formula
C21H30N4O4
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 leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Leucine and derivatives
Alternative Parents
N-carbamoyl-alpha amino acids and derivatives / Alpha amino acid amides / Morpholine carboxylic acids and derivatives / Benzylethers / N-acyl amines / Ureas / Secondary carboxylic acid amides / Oxacyclic compounds / Nitriles / Dialkyl ethers
show 5 more
Substituents
Alpha-amino acid amide / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzylether / Carbonic acid derivative / Carbonitrile / Carbonyl group / Carboxamide group / Dialkyl ether
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
ureas, nitrile, morpholines (CHEBI:41203)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
LXEDKIMJQBOMSU-MOPGFXCFSA-N
InChI
InChI=1S/C21H30N4O4/c1-16(2)12-19(24-21(27)25-8-10-28-11-9-25)20(26)23-18(13-22)15-29-14-17-6-4-3-5-7-17/h3-7,16,18-19H,8-12,14-15H2,1-2H3,(H,23,26)(H,24,27)/t18-,19+/m1/s1
IUPAC Name
(2S)-N-[(1R)-2-(benzyloxy)-1-cyanoethyl]-4-methyl-2-[(morpholine-4-carbonyl)amino]pentanamide
SMILES
[H][C@@](COCC1=CC=CC=C1)(NC(=O)[C@]([H])(CC(C)C)NC(=O)N1CCOCC1)C#N

References

General References
Not Available
PubChem Compound
5287799
PubChem Substance
46508762
ChemSpider
4450096
BindingDB
50121548
ChEMBL
CHEMBL153813
ZINC
ZINC000006616189
PDBe Ligand
BLN
PDB Entries
1ms6

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 Solubility0.126 mg/mLALOGPS
logP1.1ALOGPS
logP1.23Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)11.75Chemaxon
pKa (Strongest Basic)-1.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area103.69 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity108.34 m3·mol-1Chemaxon
Polarizability42.5 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8639
Blood Brain Barrier-0.8903
Caco-2 permeable-0.7369
P-glycoprotein substrateSubstrate0.8776
P-glycoprotein inhibitor IInhibitor0.931
P-glycoprotein inhibitor IINon-inhibitor0.9495
Renal organic cation transporterNon-inhibitor0.8435
CYP450 2C9 substrateNon-substrate0.8434
CYP450 2D6 substrateNon-substrate0.7927
CYP450 3A4 substrateSubstrate0.5869
CYP450 1A2 substrateNon-inhibitor0.9316
CYP450 2C9 inhibitorNon-inhibitor0.7371
CYP450 2D6 inhibitorNon-inhibitor0.9528
CYP450 2C19 inhibitorNon-inhibitor0.638
CYP450 3A4 inhibitorInhibitor0.6285
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9508
Ames testNon AMES toxic0.7436
CarcinogenicityNon-carcinogens0.8838
BiodegradationNot ready biodegradable0.9059
Rat acute toxicity2.4503 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6596
hERG inhibition (predictor II)Inhibitor0.6137
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/MSsplash10-0f6t-2290500000-a869527cd4527e3b9eed
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k96-1590200000-cefe664c3e64fdbf6e26
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f7c-5492200000-3e75e22ec4357554d0f3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-3930000000-e033bf69722123746df6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ko-9721000000-15abf7e01ac507372ea5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bti-8911000000-d08620aa4d7657b80bb3
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]-196.8043
predicted
DeepCCS 1.0 (2019)
[M+H]+199.19987
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.11241
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52