(2S,3S)-4-cyclopropyl-3-{(3R,5R)-3-[2-fluoro-4-(methylsulfonyl)phenyl]-1,2,4-oxadiazolidin-5-yl}-1-[(3S)-3-fluoropyrrolidin-1-yl]-1-oxobutan-2-amine

Identification

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Name
(2S,3S)-4-cyclopropyl-3-{(3R,5R)-3-[2-fluoro-4-(methylsulfonyl)phenyl]-1,2,4-oxadiazolidin-5-yl}-1-[(3S)-3-fluoropyrrolidin-1-yl]-1-oxobutan-2-amine
Accession Number
DB06993
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: 458.523
Monoisotopic: 458.179932504
Chemical Formula
C20H28F2N4O4S
InChI Key
PTAHVQJZNFGPHN-WFWWEWPISA-N
InChI
InChI=1S/C20H28F2N4O4S/c1-31(28,29)13-4-5-14(16(22)9-13)18-24-19(30-25-18)15(8-11-2-3-11)17(23)20(27)26-7-6-12(21)10-26/h4-5,9,11-12,15,17-19,24-25H,2-3,6-8,10,23H2,1H3/t12-,15-,17-,18+,19?/m0/s1
IUPAC Name
(2S,3S)-2-amino-4-cyclopropyl-3-[(3R)-3-(2-fluoro-4-methanesulfonylphenyl)-1,2,4-oxadiazolidin-5-yl]-1-[(3S)-3-fluoropyrrolidin-1-yl]butan-1-one
SMILES
[H][C@@](N)(C(=O)N1CC[C@]([H])(F)C1)[C@]([H])(CC1CC1)C1([H])N[C@]([H])(NO1)C1=C(F)C=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
60206636
PubChem Substance
99443464
ChemSpider
64873350
HET
315
PDB Entries
3c43

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 Solubility0.654 mg/mLALOGPS
logP0.38ALOGPS
logP0.72ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)16.17ChemAxon
pKa (Strongest Basic)8.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.76 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.31 m3·mol-1ChemAxon
Polarizability44.86 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier-0.5742
Caco-2 permeable-0.6453
P-glycoprotein substrateSubstrate0.7203
P-glycoprotein inhibitor INon-inhibitor0.8433
P-glycoprotein inhibitor IINon-inhibitor0.9862
Renal organic cation transporterNon-inhibitor0.8914
CYP450 2C9 substrateNon-substrate0.6544
CYP450 2D6 substrateNon-substrate0.8004
CYP450 3A4 substrateNon-substrate0.5505
CYP450 1A2 substrateNon-inhibitor0.7721
CYP450 2C9 inhibitorNon-inhibitor0.6446
CYP450 2D6 inhibitorNon-inhibitor0.8483
CYP450 2C19 inhibitorNon-inhibitor0.6623
CYP450 3A4 inhibitorNon-inhibitor0.7412
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7369
Ames testNon AMES toxic0.579
CarcinogenicityNon-carcinogens0.7465
BiodegradationNot ready biodegradable0.9759
Rat acute toxicity2.5478 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9926
hERG inhibition (predictor II)Inhibitor0.7084
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

Classification
Not classified

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