(2S,3S)-3-{3-[2-chloro-4-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-yl}-1-cyclopentylidene-4-cyclopropyl-1-fluorobutan-2-amine

Identification

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Name
(2S,3S)-3-{3-[2-chloro-4-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-yl}-1-cyclopentylidene-4-cyclopropyl-1-fluorobutan-2-amine
Accession Number
DB06994
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: 453.958
Monoisotopic: 453.128918283
Chemical Formula
C21H25ClFN3O3S
InChI Key
XCCSSVMRGIQMGF-LPHOPBHVSA-N
InChI
InChI=1S/C21H25ClFN3O3S/c1-30(27,28)14-8-9-15(17(22)11-14)20-25-21(29-26-20)16(10-12-6-7-12)19(24)18(23)13-4-2-3-5-13/h8-9,11-12,16,19H,2-7,10,24H2,1H3/t16-,19-/m0/s1
IUPAC Name
(2S,3S)-3-[3-(2-chloro-4-methanesulfonylphenyl)-1,2,4-oxadiazol-5-yl]-1-cyclopentylidene-4-cyclopropyl-1-fluorobutan-2-amine
SMILES
[H][C@@](N)(C(F)=C1CCCC1)[C@]([H])(CC1CC1)C1=NC(=NO1)C1=CC=C(C=C1Cl)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
24768547
PubChem Substance
99443465
ChemSpider
25037426
BindingDB
50374938
ChEMBL
CHEMBL1185242
HET
317
PDB Entries
3c45

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 Solubility0.0262 mg/mLALOGPS
logP3.65ALOGPS
logP3.64ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)19.65ChemAxon
pKa (Strongest Basic)7.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area99.08 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity126.23 m3·mol-1ChemAxon
Polarizability46.63 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7837
Caco-2 permeable-0.5836
P-glycoprotein substrateNon-substrate0.6765
P-glycoprotein inhibitor INon-inhibitor0.83
P-glycoprotein inhibitor IINon-inhibitor0.9752
Renal organic cation transporterNon-inhibitor0.8836
CYP450 2C9 substrateNon-substrate0.708
CYP450 2D6 substrateNon-substrate0.7931
CYP450 3A4 substrateNon-substrate0.5709
CYP450 1A2 substrateNon-inhibitor0.6503
CYP450 2C9 inhibitorNon-inhibitor0.6142
CYP450 2D6 inhibitorNon-inhibitor0.8482
CYP450 2C19 inhibitorNon-inhibitor0.5554
CYP450 3A4 inhibitorNon-inhibitor0.6711
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7387
Ames testNon AMES toxic0.5867
CarcinogenicityNon-carcinogens0.7646
BiodegradationNot ready biodegradable0.9967
Rat acute toxicity2.6856 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9824
hERG inhibition (predictor II)Non-inhibitor0.7051
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 phenyloxadiazoles. These are polycyclic aromatic compounds containing a benzene ring linked to a 1,2,4-oxadiazole ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Oxadiazoles
Direct Parent
Phenyloxadiazoles
Alternative Parents
Benzenesulfonyl compounds / Aralkylamines / Chlorobenzenes / Aryl chlorides / Sulfones / Heteroaromatic compounds / Vinyl fluorides / Oxacyclic compounds / Azacyclic compounds / Fluoroalkenes
show 7 more
Substituents
Phenyl-1,2,4-oxadiazole / Benzenesulfonyl group / Chlorobenzene / Halobenzene / Aralkylamine / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Heteroaromatic compound
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

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 December 02, 2019 07:33