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Identification
- Generic Name
- (2R)-1-[(4-tert-butylphenyl)sulfonyl]-2-methyl-4-(4-nitrophenyl)piperazine
- DrugBank Accession Number
- DB07049
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (2R)-1-[(4-tert-butylphenyl)sulfonyl]-2-methyl-4-(4-nitrophenyl)piperazine (DB07049)
- Weight
- Average: 417.522
Monoisotopic: 417.172227057 - Chemical Formula
- C21H27N3O4S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism U11-beta-hydroxysteroid dehydrogenase 1 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 phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- Phenylpiperazines
- Alternative Parents
- N-arylpiperazines / Benzenesulfonamides / Benzenesulfonyl compounds / Phenylpropanes / Nitrobenzenes / Aniline and substituted anilines / Dialkylarylamines / Nitroaromatic compounds / Organosulfonamides / Sulfonyls show 6 more
- Substituents
- Allyl-type 1,3-dipolar organic compound / Amine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / C-nitro compound / Dialkylarylamine 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
- SOFGQQQVQZQJFS-MRXNPFEDSA-N
- InChI
- InChI=1S/C21H27N3O4S/c1-16-15-22(18-7-9-19(10-8-18)24(25)26)13-14-23(16)29(27,28)20-11-5-17(6-12-20)21(2,3)4/h5-12,16H,13-15H2,1-4H3/t16-/m1/s1
- IUPAC Name
- (2R)-1-(4-tert-butylbenzenesulfonyl)-2-methyl-4-(4-nitrophenyl)piperazine
- SMILES
- [H][C@@]1(C)CN(CCN1S(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)[N+]([O-])=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 24812720
- PubChem Substance
- 99443520
- ChemSpider
- 23315644
- BindingDB
- 32573
- ChEMBL
- CHEMBL427896
- ZINC
- ZINC000024980987
- PDBe Ligand
- 3CZ
- PDB Entries
- 3czr
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 0.00784 mg/mL ALOGPS logP 4.05 ALOGPS logP 4.67 Chemaxon logS -4.7 ALOGPS pKa (Strongest Basic) -0.39 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 83.76 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 113.96 m3·mol-1 Chemaxon Polarizability 45.23 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 No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.7237 Caco-2 permeable - 0.598 P-glycoprotein substrate Substrate 0.758 P-glycoprotein inhibitor I Inhibitor 0.5606 P-glycoprotein inhibitor II Non-inhibitor 0.5326 Renal organic cation transporter Non-inhibitor 0.7378 CYP450 2C9 substrate Non-substrate 0.8145 CYP450 2D6 substrate Non-substrate 0.7985 CYP450 3A4 substrate Substrate 0.5729 CYP450 1A2 substrate Non-inhibitor 0.8594 CYP450 2C9 inhibitor Non-inhibitor 0.6308 CYP450 2D6 inhibitor Non-inhibitor 0.7897 CYP450 2C19 inhibitor Inhibitor 0.646 CYP450 3A4 inhibitor Inhibitor 0.6481 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5996 Ames test Non AMES toxic 0.5265 Carcinogenicity Non-carcinogens 0.676 Biodegradation Not ready biodegradable 0.9928 Rat acute toxicity 2.5395 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5612 hERG inhibition (predictor II) Non-inhibitor 0.5165
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key 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]- 188.15576 predictedDeepCCS 1.0 (2019) [M+H]+ 190.51378 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.95938 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Controls the reversible conversion of biologically active glucocorticoids such as cortisone to cortisol, and 11-dehydrocorticosterone to corticosterone in the presence of NADP(H) (PubMed:10497248, PubMed:12460758, PubMed:14973125, PubMed:15152005, PubMed:15280030, PubMed:17593962, PubMed:21453287, PubMed:27927697, PubMed:30902677). Participates in the corticosteroid receptor-mediated anti-inflammatory response, as well as metabolic and homeostatic processes (PubMed:10497248, PubMed:12414862, PubMed:15152005, PubMed:21453287). Plays a role in the secretion of aqueous humor in the eye, maintaining a normotensive, intraocular environment (PubMed:11481269). Bidirectional in vitro, predominantly functions as a reductase in vivo, thereby increasing the concentration of active glucocorticoids (PubMed:10497248, PubMed:11481269, PubMed:12414862, PubMed:12460758). It has broad substrate specificity, besides glucocorticoids, it accepts other steroid and sterol substrates (PubMed:15095019, PubMed:15152005, PubMed:17593962, PubMed:21453287). Interconverts 7-oxo- and 7-hydroxy-neurosteroids such as 7-oxopregnenolone and 7beta-hydroxypregnenolone, 7-oxodehydroepiandrosterone (3beta-hydroxy-5-androstene-7,17-dione) and 7beta-hydroxydehydroepiandrosterone (3beta,7beta-dihydroxyandrost-5-en-17-one), among others (PubMed:17593962). Catalyzes the stereo-specific conversion of the major dietary oxysterol, 7-ketocholesterol (7-oxocholesterol), into the more polar 7-beta-hydroxycholesterol metabolite (PubMed:15095019, PubMed:15152005). 7-oxocholesterol is one of the most important oxysterols, it participates in several events such as induction of apoptosis, accumulation in atherosclerotic lesions, lipid peroxidation, and induction of foam cell formation (PubMed:15095019). Mediates the 7-oxo reduction of 7-oxolithocholate mainly to chenodeoxycholate, and to a lesser extent to ursodeoxycholate, both in its free form and when conjugated to glycine or taurine, providing a link between glucocorticoid activation and bile acid metabolism (PubMed:21453287). Catalyzes the synthesis of 7-beta-25-dihydroxycholesterol from 7-oxo-25-hydroxycholesterol in vitro, which acts as a ligand for the G-protein-coupled receptor (GPCR) Epstein-Barr virus-induced gene 2 (EBI2) and may thereby regulate immune cell migration (PubMed:30902677)
- Specific Function
- 11-beta-hydroxysteroid dehydrogenase (NADP+) activity
- Gene Name
- HSD11B1
- Uniprot ID
- P28845
- Uniprot Name
- 11-beta-hydroxysteroid dehydrogenase 1
- Molecular Weight
- 32400.665 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 21:18 / Updated at June 12, 2020 16:52