(5S,8R,9S,10S,13R,14S,17S)-13-{2-[(3,5-DIFLUOROBENZYL)OXY]ETHYL}-17-HYDROXY-10-METHYLHEXADECAHYDRO-3H-CYCLOPENTA[A]PHENANTHREN-3-ONE
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Identification
- Generic Name
- (5S,8R,9S,10S,13R,14S,17S)-13-{2-[(3,5-DIFLUOROBENZYL)OXY]ETHYL}-17-HYDROXY-10-METHYLHEXADECAHYDRO-3H-CYCLOPENTA[A]PHENANTHREN-3-ONE
- DrugBank Accession Number
- DB07717
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 446.5697
Monoisotopic: 446.263251428 - Chemical Formula
- C27H36F2O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
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
- 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 estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Estrane steroids
- Direct Parent
- Estrogens and derivatives
- Alternative Parents
- 3-oxo-5-alpha-steroids / 17-hydroxysteroids / Benzylethers / Fluorobenzenes / Aryl fluorides / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Dialkyl ethers / Organofluorides show 2 more
- Substituents
- 17-hydroxysteroid / 3-oxo-5-alpha-steroid / 3-oxosteroid / Alcohol / Aromatic homopolycyclic compound / Aryl fluoride / Aryl halide / Benzenoid / Benzylether / Carbonyl group show 18 more
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- AJODXHGZHBERGJ-JLYQOUBASA-N
- InChI
- InChI=1S/C27H36F2O3/c1-26-8-6-21(30)14-18(26)2-3-22-23(26)7-9-27(24(22)4-5-25(27)31)10-11-32-16-17-12-19(28)15-20(29)13-17/h12-13,15,18,22-25,31H,2-11,14,16H2,1H3/t18-,22+,23-,24-,25-,26-,27+/m0/s1
- IUPAC Name
- (1S,3aS,3bR,5aS,9aS,9bS,11aR)-11a-{2-[(3,5-difluorophenyl)methoxy]ethyl}-1-hydroxy-9a-methyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-one
- SMILES
- [H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12CCOCC1=CC(F)=CC(F)=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 16750073
- PubChem Substance
- 99444188
- ChemSpider
- 20581191
- ChEMBL
- CHEMBL485835
- ZINC
- ZINC000016052389
- PDBe Ligand
- ENM
- PDB Entries
- 2pnu
Clinical Trials
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 0.00155 mg/mL ALOGPS logP 4.39 ALOGPS logP 5.07 Chemaxon logS -5.5 ALOGPS pKa (Strongest Acidic) 14.69 Chemaxon pKa (Strongest Basic) -2.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 119.93 m3·mol-1 Chemaxon Polarizability 48.83 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No 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 + 0.978 Caco-2 permeable + 0.6859 P-glycoprotein substrate Substrate 0.8165 P-glycoprotein inhibitor I Inhibitor 0.7279 P-glycoprotein inhibitor II Inhibitor 0.619 Renal organic cation transporter Non-inhibitor 0.6612 CYP450 2C9 substrate Non-substrate 0.7888 CYP450 2D6 substrate Non-substrate 0.7907 CYP450 3A4 substrate Substrate 0.6682 CYP450 1A2 substrate Non-inhibitor 0.812 CYP450 2C9 inhibitor Non-inhibitor 0.6038 CYP450 2D6 inhibitor Non-inhibitor 0.8773 CYP450 2C19 inhibitor Non-inhibitor 0.6231 CYP450 3A4 inhibitor Non-inhibitor 0.5605 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8944 Ames test Non AMES toxic 0.8372 Carcinogenicity Non-carcinogens 0.9108 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5253 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8659 hERG inhibition (predictor II) Inhibitor 0.7793
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0000900000-35e39a2ad7d80af14056 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-002k-0152900000-2f622b44c63ec7dfa55c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0001900000-f749b523d185e06c25a8 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-01tj-0434900000-073d4b32f88fab01bfda Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05r1-5360900000-76d8af6999693e6958d3 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-05p9-0934100000-1e11feea929d54705bb5 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]- 208.49107 predictedDeepCCS 1.0 (2019) [M+H]+ 210.38646 predictedDeepCCS 1.0 (2019) [M+Na]+ 216.04362 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsAndrogen receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 98987.9 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 21:25 / Updated at June 12, 2020 16:52