N-cyclopropyl-N-(trans-4-pyridin-3-ylcyclohexyl)-4-[(1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl]benzamide
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Identification
- Generic Name
- N-cyclopropyl-N-(trans-4-pyridin-3-ylcyclohexyl)-4-[(1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl]benzamide
- DrugBank Accession Number
- DB07619
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 432.4786
Monoisotopic: 432.202462733 - Chemical Formula
- C24H27F3N2O2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
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
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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 benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Benzamides
- Alternative Parents
- Benzoyl derivatives / Pyridines and derivatives / Tertiary carboxylic acid amides / Tertiary alcohols / Heteroaromatic compounds / Fluorohydrins / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organofluorides show 4 more
- Substituents
- Alcohol / Alkyl fluoride / Alkyl halide / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Benzamide / Benzoyl / Carboxamide group / Carboxylic acid derivative 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
- FLRYWTWLHWACRP-GRWTVWFQSA-N
- InChI
- InChI=1S/C24H27F3N2O2/c1-23(31,24(25,26)27)19-8-4-17(5-9-19)22(30)29(21-12-13-21)20-10-6-16(7-11-20)18-3-2-14-28-15-18/h2-5,8-9,14-16,20-21,31H,6-7,10-13H2,1H3/t16-,20-,23-/m0/s1
- IUPAC Name
- N-cyclopropyl-N-[(1r,4r)-4-(pyridin-3-yl)cyclohexyl]-4-[(2S)-1,1,1-trifluoro-2-hydroxypropan-2-yl]benzamide
- SMILES
- [H][C@@]1(CC[C@@]([H])(CC1)C1=CC=CN=C1)N(C1CC1)C(=O)C1=CC=C(C=C1)[C@](C)(O)C(F)(F)F
References
- General References
- Not Available
- External Links
- PubChem Compound
- 16726072
- PubChem Substance
- 99444090
- ChemSpider
- 23329241
- BindingDB
- 28361
- ChEMBL
- CHEMBL452587
- ZINC
- ZINC000100078683
- PDBe Ligand
- D3E
- PDB Entries
- 3d3e
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 0.00521 mg/mL ALOGPS logP 4.23 ALOGPS logP 4.27 Chemaxon logS -4.9 ALOGPS pKa (Strongest Acidic) 10.69 Chemaxon pKa (Strongest Basic) 5.49 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 53.43 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 112.22 m3·mol-1 Chemaxon Polarizability 43.88 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 Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9679 Caco-2 permeable + 0.5324 P-glycoprotein substrate Non-substrate 0.6838 P-glycoprotein inhibitor I Non-inhibitor 0.6358 P-glycoprotein inhibitor II Inhibitor 0.5725 Renal organic cation transporter Non-inhibitor 0.7638 CYP450 2C9 substrate Non-substrate 0.7278 CYP450 2D6 substrate Non-substrate 0.7814 CYP450 3A4 substrate Substrate 0.5806 CYP450 1A2 substrate Non-inhibitor 0.8094 CYP450 2C9 inhibitor Inhibitor 0.5516 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.6266 CYP450 3A4 inhibitor Inhibitor 0.5954 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5444 Ames test Non AMES toxic 0.7044 Carcinogenicity Non-carcinogens 0.7841 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.8788 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9893 hERG inhibition (predictor II) Inhibitor 0.5379
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00lr-0060900000-3a6ef0d9c234585eaba7 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03e9-0004900000-2b8c43e7daeafcd56689 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-066r-0591500000-8f5fa6acf95cc34319ae Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01x0-0026900000-651b6ce6798bba43a5aa Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0ul3-0095200000-410963040f030212232b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00lr-5982800000-065985bb16bdfef2afe8 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]- 193.98708 predictedDeepCCS 1.0 (2019) [M+H]+ 196.38266 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.29518 predictedDeepCCS 1.0 (2019)
Targets
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1. Details11-beta-hydroxysteroid dehydrogenase 1
- 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 21:24 / Updated at June 12, 2020 16:52