N-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}-5-methyl-D-tryptophan
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Identification
- Generic Name
- N-{[4-(but-2-yn-1-yloxy)phenyl]sulfonyl}-5-methyl-D-tryptophan
- DrugBank Accession Number
- DB07233
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 426.485
Monoisotopic: 426.124942514 - Chemical Formula
- C22H22N2O5S
- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Indolyl carboxylic acids and derivatives
- Direct Parent
- Indolyl carboxylic acids and derivatives
- Alternative Parents
- 3-alkylindoles / Alpha amino acids and derivatives / Benzenesulfonamides / Benzenesulfonyl compounds / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Substituted pyrroles / Organosulfonamides / Aminosulfonyl compounds show 9 more
- Substituents
- 3-alkylindole / Alkyl aryl ether / Alpha-amino acid or derivatives / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Carbonyl group show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- SFVPXERGVLDWIS-OAQYLSRUSA-N
- InChI
- InChI=1S/C22H22N2O5S/c1-3-4-11-29-17-6-8-18(9-7-17)30(27,28)24-21(22(25)26)13-16-14-23-20-10-5-15(2)12-19(16)20/h5-10,12,14,21,23-24H,11,13H2,1-2H3,(H,25,26)/t21-/m1/s1
- IUPAC Name
- (2R)-2-[4-(but-2-yn-1-yloxy)benzenesulfonamido]-3-(5-methyl-1H-indol-3-yl)propanoic acid
- SMILES
- [H][C@](CC1=CNC2=C1C=C(C)C=C2)(NS(=O)(=O)C1=CC=C(OCC#CC)C=C1)C(O)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 42627769
- PubChem Substance
- 99443704
- ChemSpider
- 24720685
- BindingDB
- 50279256
- ChEMBL
- CHEMBL527018
- ZINC
- ZINC000038225899
- PDBe Ligand
- 792
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 0.00229 mg/mL ALOGPS logP 2.77 ALOGPS logP 4.03 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 3.27 Chemaxon pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 108.49 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 113.98 m3·mol-1 Chemaxon Polarizability 44.83 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9752 Blood Brain Barrier + 0.6166 Caco-2 permeable - 0.674 P-glycoprotein substrate Substrate 0.5226 P-glycoprotein inhibitor I Non-inhibitor 0.9203 P-glycoprotein inhibitor II Non-inhibitor 0.9411 Renal organic cation transporter Non-inhibitor 0.8528 CYP450 2C9 substrate Non-substrate 0.6033 CYP450 2D6 substrate Non-substrate 0.7897 CYP450 3A4 substrate Substrate 0.521 CYP450 1A2 substrate Non-inhibitor 0.5695 CYP450 2C9 inhibitor Inhibitor 0.5 CYP450 2D6 inhibitor Non-inhibitor 0.8603 CYP450 2C19 inhibitor Non-inhibitor 0.5983 CYP450 3A4 inhibitor Inhibitor 0.8228 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6647 Ames test Non AMES toxic 0.6333 Carcinogenicity Non-carcinogens 0.7462 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4181 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9805 hERG inhibition (predictor II) Non-inhibitor 0.6689
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0080900000-c36ee20f25f0853c3b21 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0pdi-0942400000-e6d44da9ce13b0695e2b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-054k-5942400000-c21aa5becbac29857116 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a6r-0925100000-bed8921e2754c12238d2 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-9600100000-f9742ac62fd6ef677c8b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0962000000-a4b229cb991c1abef975 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]- 187.2023 predictedDeepCCS 1.0 (2019) [M+H]+ 189.59789 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.51039 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 21:19 / Updated at June 12, 2020 16:52