N-Butyl-11-[(7r,8r,9s,13s,14s,17s)-3,17-Dihydroxy-13-Methyl-7,8,9,11,12,13,14,15,16,17-Decahydro-6h-Cyclopenta[a]Phenanthren-7-Yl]-N-Methylundecanamide

Identification

Name
N-Butyl-11-[(7r,8r,9s,13s,14s,17s)-3,17-Dihydroxy-13-Methyl-7,8,9,11,12,13,14,15,16,17-Decahydro-6h-Cyclopenta[a]Phenanthren-7-Yl]-N-Methylundecanamide
Accession Number
DB03860  (EXPT00529)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
ICI 164,384
Categories
Not Available
UNII
84LT43726C
CAS number
Not Available
Weight
Average: 525.8054
Monoisotopic: 525.418194631
Chemical Formula
C34H55NO3
InChI Key
BVVFOLSZMQVDKV-KXQIQQEYSA-N
InChI
InChI=1S/C34H55NO3/c1-4-5-22-35(3)32(38)15-13-11-9-7-6-8-10-12-14-25-23-26-24-27(36)16-17-28(26)29-20-21-34(2)30(33(25)29)18-19-31(34)37/h16-17,24-25,29-31,33,36-37H,4-15,18-23H2,1-3H3/t25-,29-,30+,31+,33-,34+/m1/s1
IUPAC Name
N-butyl-11-[(1S,9R,10R,11S,14S,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-9-yl]-N-methylundecanamide
SMILES
[H][[email protected]]1(O)CC[[email protected]@]2([H])[[email protected]]3([H])[[email protected]]([H])(CCCCCCCCCCC(=O)N(C)CCCC)CC4=CC(O)=CC=C4[[email protected]@]3([H])CC[[email protected]]12C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEstrogen receptor betaNot 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
KEGG Compound
C14758
PubChem Compound
104772
PubChem Substance
46506133
ChemSpider
94580
ChEMBL
CHEMBL1222035
HET
AOE
PDB Entries
1hj1

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 Solubility0.000143 mg/mLALOGPS
logP7.88ALOGPS
logP8.12ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)10.32ChemAxon
pKa (Strongest Basic)0.29ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.77 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity157.62 m3·mol-1ChemAxon
Polarizability66.76 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9482
Caco-2 permeable+0.6647
P-glycoprotein substrateSubstrate0.821
P-glycoprotein inhibitor INon-inhibitor0.6207
P-glycoprotein inhibitor IINon-inhibitor0.6631
Renal organic cation transporterNon-inhibitor0.6958
CYP450 2C9 substrateNon-substrate0.7826
CYP450 2D6 substrateNon-substrate0.5567
CYP450 3A4 substrateSubstrate0.8458
CYP450 1A2 substrateNon-inhibitor0.5645
CYP450 2C9 inhibitorNon-inhibitor0.5821
CYP450 2D6 inhibitorNon-inhibitor0.5668
CYP450 2C19 inhibitorNon-inhibitor0.6796
CYP450 3A4 inhibitorInhibitor0.7412
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6306
Ames testNon AMES toxic0.7444
CarcinogenicityNon-carcinogens0.8426
BiodegradationNot ready biodegradable0.9953
Rat acute toxicity2.7601 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9731
hERG inhibition (predictor II)Inhibitor0.5841
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-hydroxysteroids / 17-hydroxysteroids / Phenanthrenes and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / N-acyl amines / Tertiary carboxylic acid amides / Secondary alcohols / Cyclic alcohols and derivatives / Organopnictogen compounds
show 4 more
Substituents
Estrogen-skeleton / 3-hydroxysteroid / Hydroxysteroid / 17-hydroxysteroid / Phenanthrene / Tetralin / 1-hydroxy-2-unsubstituted benzenoid / N-acyl-amine / Benzenoid / Cyclic alcohol
show 14 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
3-hydroxy steroid (CHEBI:40710)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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 June 13, 2005 07:24 / Updated on December 01, 2017 15:20