(5S,8R,9S,10S,13R,14S,17S)-13-{2-[(3,5-DIFLUOROBENZYL)OXY]ETHYL}-17-HYDROXY-10-METHYLHEXADECAHYDRO-3H-CYCLOPENTA[A]PHENANTHREN-3-ONE

Identification

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
Accession Number
DB07717
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 446.5697
Monoisotopic: 446.263251428
Chemical Formula
C27H36F2O3
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,2S,7S,10R,11S,14S,15R)-15-{2-[(3,5-difluorophenyl)methoxy]ethyl}-14-hydroxy-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
SMILES
[H][[email protected]]1(O)CC[[email protected]@]2([H])[[email protected]]3([H])CC[[email protected]@]4([H])CC(=O)CC[[email protected]]4(C)[[email protected]@]3([H])CC[[email protected]]12CCOCC1=CC(F)=CC(F)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAndrogen receptorNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
16750073
PubChem Substance
99444188
ChemSpider
20581191
ChEMBL
CHEMBL485835
HET
ENM
PDB Entries
2pnu

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.00155 mg/mLALOGPS
logP4.39ALOGPS
logP5.07ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)14.69ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.93 m3·mol-1ChemAxon
Polarizability48.99 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.978
Caco-2 permeable+0.6859
P-glycoprotein substrateSubstrate0.8165
P-glycoprotein inhibitor IInhibitor0.7279
P-glycoprotein inhibitor IIInhibitor0.619
Renal organic cation transporterNon-inhibitor0.6612
CYP450 2C9 substrateNon-substrate0.7888
CYP450 2D6 substrateNon-substrate0.7907
CYP450 3A4 substrateSubstrate0.6682
CYP450 1A2 substrateNon-inhibitor0.812
CYP450 2C9 inhibitorNon-inhibitor0.6038
CYP450 2D6 inhibitorNon-inhibitor0.8773
CYP450 2C19 inhibitorNon-inhibitor0.6231
CYP450 3A4 inhibitorNon-inhibitor0.5605
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8944
Ames testNon AMES toxic0.8372
CarcinogenicityNon-carcinogens0.9108
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5253 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8659
hERG inhibition (predictor II)Inhibitor0.7793
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Estrogen-skeleton / 3-oxosteroid / Hydroxysteroid / Oxosteroid / 17-hydroxysteroid / 3-oxo-5-alpha-steroid / Benzylether / Halobenzene / Fluorobenzene / Aryl fluoride
show 18 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10592235]

Drug created on September 15, 2010 15:25 / Updated on December 01, 2017 15:55