{4-[(2R)-pyrrolidin-2-ylmethoxy]phenyl}(4-thiophen-3-ylphenyl)methanone
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Identification
- Generic Name
- {4-[(2R)-pyrrolidin-2-ylmethoxy]phenyl}(4-thiophen-3-ylphenyl)methanone
- DrugBank Accession Number
- DB07237
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 363.473
Monoisotopic: 363.129299611 - Chemical Formula
- C22H21NO2S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ULeukotriene A-4 hydrolase 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 benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzophenones
- Direct Parent
- Benzophenones
- Alternative Parents
- Diphenylmethanes / Aryl-phenylketones / Phenoxy compounds / Phenol ethers / Benzoyl derivatives / Alkyl aryl ethers / Thiophenes / Pyrrolidines / Heteroaromatic compounds / Dialkylamines show 4 more
- Substituents
- Alkyl aryl ether / Amine / Aromatic heteromonocyclic compound / Aryl ketone / Aryl-phenylketone / Azacycle / Benzophenone / Benzoyl / Diphenylmethane / Ether show 16 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
- VUWFJUJWAWMRQN-HXUWFJFHSA-N
- InChI
- InChI=1S/C22H21NO2S/c24-22(17-5-3-16(4-6-17)19-11-13-26-15-19)18-7-9-21(10-8-18)25-14-20-2-1-12-23-20/h3-11,13,15,20,23H,1-2,12,14H2/t20-/m1/s1
- IUPAC Name
- (2R)-2-({4-[4-(thiophen-3-yl)benzoyl]phenoxy}methyl)pyrrolidine
- SMILES
- [H][C@]1(COC2=CC=C(C=C2)C(=O)C2=CC=C(C=C2)C2=CSC=C2)CCCN1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 44129624
- PubChem Substance
- 99443708
- ChemSpider
- 24626134
- BindingDB
- 50294162
- ChEMBL
- CHEMBL561639
- ZINC
- ZINC000039257802
- PDBe Ligand
- 798
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 0.00064 mg/mL ALOGPS logP 4.78 ALOGPS logP 4.8 Chemaxon logS -5.8 ALOGPS pKa (Strongest Basic) 10.47 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 38.33 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 105.27 m3·mol-1 Chemaxon Polarizability 41.28 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.971 Caco-2 permeable - 0.5303 P-glycoprotein substrate Substrate 0.576 P-glycoprotein inhibitor I Non-inhibitor 0.67 P-glycoprotein inhibitor II Inhibitor 0.8387 Renal organic cation transporter Inhibitor 0.626 CYP450 2C9 substrate Non-substrate 0.8042 CYP450 2D6 substrate Non-substrate 0.6228 CYP450 3A4 substrate Non-substrate 0.6316 CYP450 1A2 substrate Inhibitor 0.6997 CYP450 2C9 inhibitor Non-inhibitor 0.6681 CYP450 2D6 inhibitor Inhibitor 0.6814 CYP450 2C19 inhibitor Inhibitor 0.558 CYP450 3A4 inhibitor Non-inhibitor 0.7319 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9096 Ames test Non AMES toxic 0.7457 Carcinogenicity Non-carcinogens 0.9391 Biodegradation Not ready biodegradable 0.9879 Rat acute toxicity 2.4170 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.799 hERG inhibition (predictor II) Inhibitor 0.5306
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03ea-4009000000-4474469ab96e85d42f7e Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0019000000-dbe66a3639401d858778 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-9204000000-7b7c6dfdf2c76804a807 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-2092000000-8c80f3da5b9000a3c0b7 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0309-0729000000-fdb0a0c8f8fee9451bcf Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0fk9-2092000000-c85d45e5d0034fa23a6e 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]- 183.33789 predictedDeepCCS 1.0 (2019) [M+H]+ 185.69589 predictedDeepCCS 1.0 (2019) [M+Na]+ 192.3994 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsLeukotriene A-4 hydrolase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Bifunctional zinc metalloenzyme that comprises both epoxide hydrolase (EH) and aminopeptidase activities. Acts as an epoxide hydrolase to catalyze the conversion of LTA4 to the pro-inflammatory mediator leukotriene B4 (LTB4) (PubMed:11917124, PubMed:12207002, PubMed:15078870, PubMed:18804029, PubMed:1897988, PubMed:1975494, PubMed:2244921). Has also aminopeptidase activity, with high affinity for N-terminal arginines of various synthetic tripeptides (PubMed:18804029, PubMed:20813919). In addition to its pro-inflammatory EH activity, may also counteract inflammation by its aminopeptidase activity, which inactivates by cleavage another neutrophil attractant, the tripeptide Pro-Gly-Pro (PGP), a bioactive fragment of collagen generated by the action of matrix metalloproteinase-9 (MMP9) and prolylendopeptidase (PREPL) (PubMed:20813919, PubMed:24591641). Involved also in the biosynthesis of resolvin E1 and 18S-resolvin E1 from eicosapentaenoic acid, two lipid mediators that show potent anti-inflammatory and pro-resolving actions (PubMed:21206090)
- Specific Function
- aminopeptidase activity
- Gene Name
- LTA4H
- Uniprot ID
- P09960
- Uniprot Name
- Leukotriene A-4 hydrolase
- Molecular Weight
- 69284.64 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