(3S)-1-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}pyrrolidine-3-thiol
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Identification
- Generic Name
- (3S)-1-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}pyrrolidine-3-thiol
- DrugBank Accession Number
- DB06943
- Background
(3S)-1-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}pyrrolidine-3-thiol is a solid. This compound belongs to the benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. This substance is known to target disintegrin and metalloproteinase domain-containing protein 17.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 311.42
Monoisotopic: 311.064984795 - Chemical Formula
- C14H17NO3S2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDisintegrin and metalloproteinase domain-containing protein 17 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 benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzenesulfonamides
- Direct Parent
- Benzenesulfonamides
- Alternative Parents
- Benzenesulfonyl compounds / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Organosulfonamides / Sulfonyls / Pyrrolidines / Azacyclic compounds / Alkylthiols / Organopnictogen compounds show 3 more
- Substituents
- Alkyl aryl ether / Alkylthiol / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Ether / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide show 13 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
- BLIQFUCBRCDFAI-ZDUSSCGKSA-N
- InChI
- InChI=1S/C14H17NO3S2/c1-2-3-10-18-12-4-6-14(7-5-12)20(16,17)15-9-8-13(19)11-15/h4-7,13,19H,8-11H2,1H3/t13-/m0/s1
- IUPAC Name
- (3S)-1-[4-(but-2-yn-1-yloxy)benzenesulfonyl]pyrrolidine-3-thiol
- SMILES
- [H][C@]1(S)CCN(C1)S(=O)(=O)C1=CC=C(OCC#CC)C=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 9861547
- PubChem Substance
- 99443414
- ChemSpider
- 8037243
- BindingDB
- 26544
- ChEMBL
- CHEMBL243024
- ZINC
- ZINC000016052299
- PDBe Ligand
- 283
- PDB Entries
- 2oi0
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 0.0177 mg/mL ALOGPS logP 3 ALOGPS logP 2.26 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 9.92 Chemaxon pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.61 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 82.57 m3·mol-1 Chemaxon Polarizability 32.66 Å3 Chemaxon Number of Rings 2 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 + 1.0 Blood Brain Barrier + 0.9801 Caco-2 permeable - 0.6127 P-glycoprotein substrate Substrate 0.5706 P-glycoprotein inhibitor I Non-inhibitor 0.5635 P-glycoprotein inhibitor II Non-inhibitor 0.9038 Renal organic cation transporter Non-inhibitor 0.5799 CYP450 2C9 substrate Non-substrate 0.5745 CYP450 2D6 substrate Non-substrate 0.7608 CYP450 3A4 substrate Substrate 0.5249 CYP450 1A2 substrate Non-inhibitor 0.7337 CYP450 2C9 inhibitor Non-inhibitor 0.6527 CYP450 2D6 inhibitor Non-inhibitor 0.8162 CYP450 2C19 inhibitor Inhibitor 0.5352 CYP450 3A4 inhibitor Non-inhibitor 0.6913 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5651 Ames test Non AMES toxic 0.6135 Carcinogenicity Non-carcinogens 0.8301 Biodegradation Not ready biodegradable 0.6625 Rat acute toxicity 2.5141 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5844 hERG inhibition (predictor II) Non-inhibitor 0.6449
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0udj-3930000000-cc589a146b76fe116a58 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0219000000-49e163dea0f9fe446f1a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03k9-0079000000-50cf471f12094b716bfc Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0ik9-1729000000-81371e89dd11d5994f3d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0ab9-0981000000-840fa704b75c18d50280 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fsj-7920000000-9c7c9526a874c06a9cec Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00dm-2950000000-800200d1c605f9a6d8d1 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]- 164.85289 predictedDeepCCS 1.0 (2019) [M+H]+ 167.21089 predictedDeepCCS 1.0 (2019) [M+Na]+ 173.68216 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane metalloprotease which mediates the ectodomain shedding of a myriad of transmembrane proteins including adhesion proteins, growth factor precursors and cytokines important for inflammation and immunity (PubMed:24226769, PubMed:24227843, PubMed:28060820, PubMed:28923481). Cleaves the membrane-bound precursor of TNF-alpha to its mature soluble form (PubMed:9034191, PubMed:36078095). Responsible for the proteolytical release of soluble JAM3 from endothelial cells surface (PubMed:20592283). Responsible for the proteolytic release of several other cell-surface proteins, including p75 TNF-receptor, interleukin 1 receptor type II, p55 TNF-receptor, transforming growth factor-alpha, L-selectin, growth hormone receptor, MUC1 and the amyloid precursor protein (PubMed:12441351). Acts as an activator of Notch pathway by mediating cleavage of Notch, generating the membrane-associated intermediate fragment called Notch extracellular truncation (NEXT) (PubMed:24226769). Plays a role in the proteolytic processing of ACE2 (PubMed:24227843). Plays a role in hemostasis through shedding of GP1BA, the platelet glycoprotein Ib alpha chain (By similarity). Mediates the proteolytic cleavage of LAG3, leading to release the secreted form of LAG3 (By similarity). Mediates the proteolytic cleavage of IL6R, leading to the release of secreted form of IL6R (PubMed:26876177, PubMed:28060820). Mediates the proteolytic cleavage and shedding of FCGR3A upon NK cell stimulation, a mechanism that allows for increased NK cell motility and detachment from opsonized target cells. Cleaves TREM2, resulting in shedding of the TREM2 ectodomain (PubMed:28923481)
- Specific Function
- cytokine binding
- Gene Name
- ADAM17
- Uniprot ID
- P78536
- Uniprot Name
- Disintegrin and metalloproteinase domain-containing protein 17
- Molecular Weight
- 93020.165 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 21:17 / Updated at June 12, 2020 16:52