NAV

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

Identification

Generic Name
(2S,3S)-3-{3-[4-(METHYLSULFONYL)PHENYL]-1,2,4-OXADIAZOL-5-YL}-1-OXO-1-PYRROLIDIN-1-YLBUTAN-2-AMINE
DrugBank Accession Number
DB07067
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 378.446
Monoisotopic: 378.136175902
Chemical Formula
C17H22N4O4S
Synonyms
Not Available
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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 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
1,2,4-oxadiazole / Alpha-amino acid amide / Amine / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Azole / Benzenesulfonyl group / Benzenoid / Carbonyl group
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
N-acylpyrrolidine, ring assembly, 1,2,4-oxadiazole (CHEBI:39955)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
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
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 Solubility0.271 mg/mLALOGPS
logP0.88ALOGPS
logP0.78Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)16.17Chemaxon
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/MSsplash10-004i-0009000000-36f51585c359f8b6ba3d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1509000000-bfe7e53e155d5f52ec24
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-08i0-7039000000-91b262939b0345dde0cc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ufr-0393000000-de514a18bd1b0981a42f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kai-6493000000-775574916380b39a6af4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-9201000000-941042523d8287380a0a
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]-183.43248
predicted
DeepCCS 1.0 (2019)
[M+H]+185.82805
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.84682
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. 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. [Article]

Drug created at September 15, 2010 21:18 / Updated at June 12, 2020 16:52