(3R,4S)-1-{6-[3-(METHYLSULFONYL)PHENYL]PYRIMIDIN-4-YL}-4-(2,4,5-TRIFLUOROPHENYL)PYRROLIDIN-3-AMINE
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Identification
- Generic Name
- (3R,4S)-1-{6-[3-(METHYLSULFONYL)PHENYL]PYRIMIDIN-4-YL}-4-(2,4,5-TRIFLUOROPHENYL)PYRROLIDIN-3-AMINE
- DrugBank Accession Number
- DB07666
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 448.461
Monoisotopic: 448.118081177 - Chemical Formula
- C21H19F3N4O2S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDipeptidyl peptidase 4 Not Available Humans - 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 phenylpyrimidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrimidine ring through a CC or CN bond. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyrimidines and pyrimidine derivatives
- Direct Parent
- Phenylpyrimidines
- Alternative Parents
- Phenylpyrrolidines / Benzenesulfonyl compounds / Dialkylarylamines / Aminopyrimidines and derivatives / Aralkylamines / Fluorobenzenes / Aryl fluorides / Imidolactams / Sulfones / Pyrroles show 7 more
- Substituents
- 3-phenylpyrrolidine / 4-phenylpyrimidine / 5-phenylpyrimidine / Amine / Aminopyrimidine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle show 23 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- OAWGQHXWGXOUKV-BEFAXECRSA-N
- InChI
- InChI=1S/C21H19F3N4O2S/c1-31(29,30)13-4-2-3-12(5-13)20-8-21(27-11-26-20)28-9-15(19(25)10-28)14-6-17(23)18(24)7-16(14)22/h2-8,11,15,19H,9-10,25H2,1H3/t15-,19+/m1/s1
- IUPAC Name
- (3R,4S)-1-[6-(3-methanesulfonylphenyl)pyrimidin-4-yl]-4-(2,4,5-trifluorophenyl)pyrrolidin-3-amine
- SMILES
- [H][C@]1(N)CN(C[C@]1([H])C1=CC(F)=C(F)C=C1F)C1=CC(=NC=N1)C1=CC(=CC=C1)S(C)(=O)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 16750059
- PubChem Substance
- 99444137
- ChemSpider
- 20581178
- BindingDB
- 15498
- ChEMBL
- CHEMBL1232261
- ZINC
- ZINC000014958755
- PDBe Ligand
- DLI
- PDB Entries
- 2oag
Clinical Trials
- 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
Property Value Source Water Solubility 0.0151 mg/mL ALOGPS logP 2.26 ALOGPS logP 2.82 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 16.19 Chemaxon pKa (Strongest Basic) 9.44 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 89.18 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 111.91 m3·mol-1 Chemaxon Polarizability 43.04 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9916 Blood Brain Barrier + 0.9402 Caco-2 permeable - 0.5445 P-glycoprotein substrate Substrate 0.6109 P-glycoprotein inhibitor I Non-inhibitor 0.8549 P-glycoprotein inhibitor II Non-inhibitor 0.9748 Renal organic cation transporter Non-inhibitor 0.6339 CYP450 2C9 substrate Non-substrate 0.7449 CYP450 2D6 substrate Non-substrate 0.7438 CYP450 3A4 substrate Substrate 0.5123 CYP450 1A2 substrate Non-inhibitor 0.5311 CYP450 2C9 inhibitor Non-inhibitor 0.6059 CYP450 2D6 inhibitor Non-inhibitor 0.7581 CYP450 2C19 inhibitor Non-inhibitor 0.5649 CYP450 3A4 inhibitor Inhibitor 0.6851 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.627 Ames test Non AMES toxic 0.6068 Carcinogenicity Non-carcinogens 0.7728 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6239 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9672 hERG inhibition (predictor II) Inhibitor 0.6936
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000t-0000900000-5e28449fc0cb8aa6d392 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00kb-4370900000-4acefb70d0be8110daf1 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001j-0001900000-c50d4ea5c4f46a604485 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-002b-4100900000-93f54caae249bde1aadc Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-02ta-1269800000-0c1d81469e83b3eb1e7b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-06w9-7391600000-8fc53f4031bd764c16fe Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 202.13383 predictedDeepCCS 1.0 (2019) [M+H]+ 204.52939 predictedDeepCCS 1.0 (2019) [M+Na]+ 210.4421 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsDipeptidyl peptidase 4
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation (PubMed:10900005, PubMed:10951221, PubMed:11772392, PubMed:17287217). Acts as a positive regulator of T-cell coactivation, by binding at least ADA, CAV1, IGF2R, and PTPRC (PubMed:10900005, PubMed:10951221, PubMed:11772392, PubMed:14691230). Its binding to CAV1 and CARD11 induces T-cell proliferation and NF-kappa-B activation in a T-cell receptor/CD3-dependent manner (PubMed:17287217). Its interaction with ADA also regulates lymphocyte-epithelial cell adhesion (PubMed:11772392). In association with FAP is involved in the pericellular proteolysis of the extracellular matrix (ECM), the migration and invasion of endothelial cells into the ECM (PubMed:10593948, PubMed:16651416). May be involved in the promotion of lymphatic endothelial cells adhesion, migration and tube formation (PubMed:18708048). When overexpressed, enhanced cell proliferation, a process inhibited by GPC3 (PubMed:17549790). Acts also as a serine exopeptidase with a dipeptidyl peptidase activity that regulates various physiological processes by cleaving peptides in the circulation, including many chemokines, mitogenic growth factors, neuropeptides and peptide hormones such as brain natriuretic peptide 32 (PubMed:10570924, PubMed:16254193). Removes N-terminal dipeptides sequentially from polypeptides having unsubstituted N-termini provided that the penultimate residue is proline (PubMed:10593948).
- Specific Function
- aminopeptidase activity
- Gene Name
- DPP4
- Uniprot ID
- P27487
- Uniprot Name
- Dipeptidyl peptidase 4
- Molecular Weight
- 88277.935 Da
References
- 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 21:24 / Updated at June 12, 2020 16:52