(2S,3S)-3-{3-[4-(METHYLSULFONYL)PHENYL]-1,2,4-OXADIAZOL-5-YL}-1-OXO-1-PYRROLIDIN-1-YLBUTAN-2-AMINE

Identification

Name
(2S,3S)-3-{3-[4-(METHYLSULFONYL)PHENYL]-1,2,4-OXADIAZOL-5-YL}-1-OXO-1-PYRROLIDIN-1-YLBUTAN-2-AMINE
Accession Number
DB07067
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 378.446
Monoisotopic: 378.136175902
Chemical Formula
C17H22N4O4S
InChI Key
SQCDMTZMCHZYGO-FZMZJTMJSA-N
InChI
InChI=1S/C17H22N4O4S/c1-11(14(18)17(22)21-9-3-4-10-21)16-19-15(20-25-16)12-5-7-13(8-6-12)26(2,23)24/h5-8,11,14H,3-4,9-10,18H2,1-2H3/t11-,14-/m0/s1
IUPAC Name
(2S,3S)-2-amino-3-[3-(4-methanesulfonylphenyl)-1,2,4-oxadiazol-5-yl]-1-(pyrrolidin-1-yl)butan-1-one
SMILES
[H][C@@](N)(C(=O)N1CCCC1)[C@]([H])(C)C1=NC(=NO1)C1=CC=C(C=C1)S(C)(=O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDipeptidyl peptidase 4Not 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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
PubChem Compound
23645698
PubChem Substance
99443538
ChemSpider
24684245
BindingDB
11658
ChEBI
39955
ChEMBL
CHEMBL374936
ZINC
ZINC000014948434
PDBe Ligand
3TP
PDB Entries
2hha

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.271 mg/mLALOGPS
logP0.88ALOGPS
logP0.78ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)19.22ChemAxon
pKa (Strongest Basic)7.53ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area119.39 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.15 m3·mol-1ChemAxon
Polarizability39.89 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9916
Blood Brain Barrier+0.7793
Caco-2 permeable-0.6455
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.9417
P-glycoprotein inhibitor IINon-inhibitor0.9737
Renal organic cation transporterNon-inhibitor0.802
CYP450 2C9 substrateNon-substrate0.7295
CYP450 2D6 substrateNon-substrate0.7771
CYP450 3A4 substrateNon-substrate0.5407
CYP450 1A2 substrateNon-inhibitor0.8894
CYP450 2C9 inhibitorNon-inhibitor0.666
CYP450 2D6 inhibitorNon-inhibitor0.9037
CYP450 2C19 inhibitorNon-inhibitor0.7574
CYP450 3A4 inhibitorNon-inhibitor0.9345
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9052
Ames testNon AMES toxic0.615
CarcinogenicityNon-carcinogens0.6975
BiodegradationNot ready biodegradable0.6537
Rat acute toxicity2.4517 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9903
hERG inhibition (predictor II)Non-inhibitor0.592
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Phenyloxadiazoles / Benzenesulfonyl compounds / N-acylpyrrolidines / Aralkylamines / Tertiary carboxylic acid amides / Sulfones / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Alpha-amino acid amide / Phenyl-1,2,4-oxadiazole / Benzenesulfonyl group / N-acylpyrrolidine / Aralkylamine / Monocyclic benzene moiety / Benzenoid / 1,2,4-oxadiazole / Azole / Oxadiazole
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
N-acylpyrrolidine, ring assembly, 1,2,4-oxadiazole (CHEBI:39955)

Targets

Details
1. Dipeptidyl peptidase 4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by bindi...
Gene Name
DPP4
Uniprot ID
P27487
Uniprot Name
Dipeptidyl peptidase 4
Molecular Weight
88277.935 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. [PubMed:10592235]

Drug created on September 15, 2010 15:18 / Updated on June 12, 2020 10:52

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