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Morpholine-4-Carboxylic Acid [1-(2-Benzylsulfanyl-1-Formyl-Ethylcarbamoyl)-2-Phenyl-Ethyl]-Amide

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Identification

Generic Name
Morpholine-4-Carboxylic Acid [1-(2-Benzylsulfanyl-1-Formyl-Ethylcarbamoyl)-2-Phenyl-Ethyl]-Amide
DrugBank Accession Number
DB03984
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 455.57
Monoisotopic: 455.187877121
Chemical Formula
C24H29N3O4S
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 phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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
Phenylalanine and derivatives
Alternative Parents
N-carbamoyl-alpha amino acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / Morpholine carboxylic acids and derivatives / Fatty amides / Ureas / Secondary carboxylic acid amides / Sulfenyl compounds / Oxacyclic compounds / Azacyclic compounds
show 7 more
Substituents
Aldehyde / Alpha-amino acid amide / Amphetamine or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonic acid derivative / Carbonyl group / Carboxamide group / Dialkyl ether
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
ureas, morpholines, amino aldehyde, L-phenylalanine derivative (CHEBI:41335)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MWTQNXVXPLTHJB-YADHBBJMSA-N
InChI
InChI=1S/C24H29N3O4S/c28-16-21(18-32-17-20-9-5-2-6-10-20)25-23(29)22(15-19-7-3-1-4-8-19)26-24(30)27-11-13-31-14-12-27/h1-10,16,21-22H,11-15,17-18H2,(H,25,29)(H,26,30)/t21-,22+/m1/s1
IUPAC Name
(2S)-N-[(2R)-1-(benzylsulfanyl)-3-oxopropan-2-yl]-2-[(morpholine-4-carbonyl)amino]-3-phenylpropanamide
SMILES
[H][C@@](CSCC1=CC=CC=C1)(NC(=O)[C@]([H])(CC1=CC=CC=C1)NC(=O)N1CCOCC1)C=O

References

General References
Not Available
PubChem Compound
5287870
PubChem Substance
46507654
ChemSpider
4450157
ZINC
ZINC000012504073
PDBe Ligand
C4P
PDB Entries
1nqc

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 Solubility0.00494 mg/mLALOGPS
logP1.94ALOGPS
logP2.15Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)12.69Chemaxon
pKa (Strongest Basic)-2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area87.74 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity125.52 m3·mol-1Chemaxon
Polarizability48.71 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8839
Blood Brain Barrier+0.5
Caco-2 permeable-0.7365
P-glycoprotein substrateSubstrate0.8114
P-glycoprotein inhibitor IInhibitor0.7389
P-glycoprotein inhibitor IINon-inhibitor0.9951
Renal organic cation transporterNon-inhibitor0.8026
CYP450 2C9 substrateNon-substrate0.8602
CYP450 2D6 substrateNon-substrate0.7846
CYP450 3A4 substrateNon-substrate0.6108
CYP450 1A2 substrateNon-inhibitor0.9712
CYP450 2C9 inhibitorNon-inhibitor0.798
CYP450 2D6 inhibitorNon-inhibitor0.9506
CYP450 2C19 inhibitorInhibitor0.5693
CYP450 3A4 inhibitorInhibitor0.5785
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9397
Ames testNon AMES toxic0.7446
CarcinogenicityNon-carcinogens0.936
BiodegradationNot ready biodegradable0.8617
Rat acute toxicity2.2474 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6535
hERG inhibition (predictor II)Inhibitor0.515
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/MSsplash10-0a4l-5028900000-852b785f0de1b3f99c03
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0913500000-60f0d304c9266fc027b5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dj-3971000000-46c8d1611d49e7cb4dfb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000f-4149500000-520bab8f606813c9c145
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-8901100000-8b79a70ea7827d7d1023
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xs-2931100000-dbd32420c3ca880b8de6
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]-198.73683
predicted
DeepCCS 1.0 (2019)
[M+H]+201.13239
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.0449
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]
  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