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Morpholine-4-Carboxylic Acid (1-(3-Benzenesulfonyl-1-Phenethylallylcarbamoyl)-3-Methylbutyl)-Amide

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Identification

Generic Name
Morpholine-4-Carboxylic Acid (1-(3-Benzenesulfonyl-1-Phenethylallylcarbamoyl)-3-Methylbutyl)-Amide
DrugBank Accession Number
DB03837
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 527.675
Monoisotopic: 527.245391999
Chemical Formula
C28H37N3O5S
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 / Benzenesulfonyl compounds / Morpholine carboxylic acids and derivatives / N-acyl amines / Sulfones / Ureas / Secondary carboxylic acid amides / Oxacyclic compounds / Azacyclic compounds
show 6 more
Substituents
Alpha-amino acid amide / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonyl group / Benzenoid / Carbonic acid derivative / Carbonyl group / Carboxamide group / Dialkyl ether / Ether
show 23 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
YUMYYTORLYHUFW-ZUDLOMHPSA-N
InChI
InChI=1S/C28H37N3O5S/c1-22(2)21-26(30-28(33)31-16-18-36-19-17-31)27(32)29-24(14-13-23-9-5-3-6-10-23)15-20-37(34,35)25-11-7-4-8-12-25/h3-12,15,20,22,24,26H,13-14,16-19,21H2,1-2H3,(H,29,32)(H,30,33)/b20-15+/t24-,26-/m1/s1
IUPAC Name
(2R)-N-[(1E,3R)-1-(benzenesulfonyl)-5-phenylpent-1-en-3-yl]-4-methyl-2-{[(E)-morpholine-4-carbonyl]amino}pentanamide
SMILES
C(C)(C)C[C@H](C(=O)N[C@H](CCC1=CC=CC=C1)\C=C\S(=O)(=O)C1=CC=CC=C1)NC(=O)N1CCOCC1

References

General References
Not Available
PubChem Compound
23648296
PubChem Substance
46506153
ChemSpider
23281169
ChEMBL
CHEMBL222649
ZINC
ZINC000012503958
PDBe Ligand
C1P

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 Solubility0.00418 mg/mLALOGPS
logP2.67ALOGPS
logP3.49Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.94Chemaxon
pKa (Strongest Basic)-1.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area104.81 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity144.3 m3·mol-1Chemaxon
Polarizability56.36 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8774
Blood Brain Barrier-0.587
Caco-2 permeable-0.6671
P-glycoprotein substrateSubstrate0.8622
P-glycoprotein inhibitor IInhibitor0.9118
P-glycoprotein inhibitor IINon-inhibitor0.9867
Renal organic cation transporterNon-inhibitor0.8743
CYP450 2C9 substrateNon-substrate0.6842
CYP450 2D6 substrateNon-substrate0.7771
CYP450 3A4 substrateSubstrate0.5374
CYP450 1A2 substrateNon-inhibitor0.921
CYP450 2C9 inhibitorNon-inhibitor0.8168
CYP450 2D6 inhibitorNon-inhibitor0.907
CYP450 2C19 inhibitorNon-inhibitor0.7995
CYP450 3A4 inhibitorInhibitor0.5957
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9437
Ames testNon AMES toxic0.6706
CarcinogenicityNon-carcinogens0.7401
BiodegradationNot ready biodegradable0.6997
Rat acute toxicity2.5115 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8901
hERG inhibition (predictor II)Non-inhibitor0.6404
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/MSsplash10-004i-0100290000-705b055b9ba37db03ee8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0101090000-7273721e7c7c17b82c5b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01y2-3309710000-08b0beb98280908ebc0d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-1910100000-51874da65e4d7dd4c5fa
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-8923400000-9220d82b57856d986977
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-02vr-8905810000-b404ac9536a1fcfe08a2
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-221.86574
predicted
DeepCCS 1.0 (2019)
[M+H]+223.76115
predicted
DeepCCS 1.0 (2019)
[M+Na]+229.66292
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. 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]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52