4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile
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Identification
- Generic Name
- 4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile
- DrugBank Accession Number
- DB07421
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile (DB07421)
- Weight
- Average: 411.3319
Monoisotopic: 411.104205252 - Chemical Formula
- C18H16F3N3O5
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UAndrogen receptor 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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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 nitrophenyl ethers. These are aromatic compounds containing a nitrobenzene moiety that carries an ether group on the benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Nitrobenzenes
- Direct Parent
- Nitrophenyl ethers
- Alternative Parents
- Trifluoromethylbenzenes / Phenylalkylamines / Phenoxy compounds / Phenol ethers / Benzonitriles / Nitroaromatic compounds / Secondary alkylarylamines / Alkyl aryl ethers / Tertiary alcohols / Propargyl-type 1,3-dipolar organic compounds show 9 more
- Substituents
- Alcohol / Alkanolamine / Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Allyl-type 1,3-dipolar organic compound / Amine / Aromatic homomonocyclic compound / Benzonitrile / C-nitro compound show 26 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- INVUBEGZQHQAMY-SJORKVTESA-N
- InChI
- InChI=1S/C18H16F3N3O5/c1-17(26,10-29-14-6-4-13(5-7-14)24(27)28)16(25)23-12-3-2-11(9-22)15(8-12)18(19,20)21/h2-8,16,23,25-26H,10H2,1H3/t16-,17+/m1/s1
- IUPAC Name
- 4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile
- SMILES
- [H][C@](O)(NC1=CC(=C(C=C1)C#N)C(F)(F)F)[C@@](C)(O)COC1=CC=C(C=C1)[N+]([O-])=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 46937071
- PubChem Substance
- 99443892
- ChemSpider
- 25057164
- ZINC
- ZINC000039037416
- PDBe Ligand
- B66
- PDB Entries
- 3b66
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 0.0107 mg/mL ALOGPS logP 2.99 ALOGPS logP 3.05 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 11.57 Chemaxon pKa (Strongest Basic) -2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 128.65 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 96.45 m3·mol-1 Chemaxon Polarizability 36.96 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 + 0.9515 Blood Brain Barrier - 0.511 Caco-2 permeable - 0.5705 P-glycoprotein substrate Non-substrate 0.5497 P-glycoprotein inhibitor I Inhibitor 0.5089 P-glycoprotein inhibitor II Non-inhibitor 0.8562 Renal organic cation transporter Non-inhibitor 0.9498 CYP450 2C9 substrate Non-substrate 0.7056 CYP450 2D6 substrate Non-substrate 0.8103 CYP450 3A4 substrate Substrate 0.5495 CYP450 1A2 substrate Non-inhibitor 0.5 CYP450 2C9 inhibitor Non-inhibitor 0.5811 CYP450 2D6 inhibitor Non-inhibitor 0.8019 CYP450 2C19 inhibitor Inhibitor 0.5069 CYP450 3A4 inhibitor Non-inhibitor 0.5894 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5783 Ames test Non AMES toxic 0.5999 Carcinogenicity Non-carcinogens 0.7029 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5807 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9732 hERG inhibition (predictor II) Non-inhibitor 0.689
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-014r-0892000000-ae25a58a8bfa5a5c2db2 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]- 173.88435 predictedDeepCCS 1.0 (2019) [M+H]+ 176.2799 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.19243 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues (PubMed:19022849). Transcription factor activity is modulated by bound coactivator and corepressor proteins like ZBTB7A that recruits NCOR1 and NCOR2 to the androgen response elements/ARE on target genes, negatively regulating androgen receptor signaling and androgen-induced cell proliferation (PubMed:20812024). Transcription activation is also down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3
- Specific Function
- androgen binding
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 99187.115 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 21:21 / Updated at June 12, 2020 16:52