Oleoyl-estrone

Identification

Name
Oleoyl-estrone
Accession Number
DB04870
Type
Small Molecule
Groups
Investigational
Description

Oleoyl-estrone (OE) is a fatty acid ester of estrone. It is a naturally circulating hormone in animals including humans. It was first reported in 1996 to cause a body fat loss effect in rats in the International Journal of Obesity and Related Metabolic Disorders. The animal research has all been conducted by the Nitrogen-Obesity Research Group of the University of Barcelona. The compound was found to potently induce body-fat loss while preserving protein stores in animals which is the ultimate goal of an anti-obesity agent as body protein loss is an undesired but inevitable (to some degree) side effect of fat loss via calorie restriction. [Wikipedia]

Structure
Thumb
Synonyms
  • Estrone 3-oleate
  • Estrone monooleate
  • Estrone oleic acid ester
  • OE
  • Oleoyl estrone
  • Oleoylestrone
External IDs
MP-101
Categories
UNII
64R56KMG1Z
CAS number
180003-17-2
Weight
Average: 534.8122
Monoisotopic: 534.407295594
Chemical Formula
C36H54O3
InChI Key
IMIPDPVHGGHVNH-YWVHRCQQSA-N
InChI
InChI=1S/C36H54O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-35(38)39-29-20-22-30-28(27-29)19-21-32-31(30)25-26-36(2)33(32)23-24-34(36)37/h10-11,20,22,27,31-33H,3-9,12-19,21,23-26H2,1-2H3/b11-10-/t31-,32-,33+,36+/m1/s1
IUPAC Name
(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl (9Z)-octadec-9-enoate
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC(=O)CCCCCCC\C=C/CCCCCCCC)C=C3

Pharmacology

Indication

For the treatment of obesity.

Pharmacodynamics

Oleoyl-estrone is a fatty acid ester of estrone, and may be directly involved in the control of body weight (PMID: 8782737).

Mechanism of action

Based on extensive preclinical studies, it is believed that oleoyl-estrone (OE) works by a dual mechanism of action. Centrally, OE appears to act at the brain's hypothalamus, resetting the body's ponderostat, the “food control center” in the brain that detects and integrates signals that control both appetite and metabolic behavior. Peripherally, OE also causes reduced storage of fat in “white fat” tissue and allows skeletal muscle to use fat as an alternate energy source.

Absorption

Orally 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
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Capromab pendetideOleoyl-estrone may decrease effectiveness of Capromab pendetide as a diagnostic agent.
Conestat alfaThe risk or severity of thromboembolism can be increased when Oleoyl-estrone is combined with Conestat alfa.
Human C1-esterase inhibitorThe risk or severity of thromboembolism can be increased when Oleoyl-estrone is combined with Human C1-esterase inhibitor.
Food Interactions
Not Available

References

General References
  1. Sanchis D, Balada F, del Mar Grasa M, Virgili J, Peinado J, Monserrat C, Fernandez-Lopez JA, Remesar X, Alemany M: Oleoyl-estrone induces the loss of body fat in rats. Int J Obes Relat Metab Disord. 1996 Jun;20(6):588-94. [PubMed:8782737]
  2. Salas A, Remesar X, Esteve M: Oleoyl-estrone treatment activates apoptotic mechanisms in white adipose tissue. Life Sci. 2007 Jan 2;80(4):293-8. Epub 2006 Sep 30. [PubMed:17055002]
External Links
PubChem Compound
6918373
PubChem Substance
175426878
ChemSpider
5293576
Wikipedia
Oleoyl-estrone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2RecruitingTreatmentAcute Agitation / Aggressive Behavior / Alzheimer Dementia (AD) / Alzheimer's Disease (AD) / Dementias / Psychosis1
2Unknown StatusTreatmentBMI >30 kg/m22

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 Solubility4.87e-06 mg/mLALOGPS
logP9.64ALOGPS
logP11.23ChemAxon
logS-8ALOGPS
pKa (Strongest Acidic)19.96ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity162.99 m3·mol-1ChemAxon
Polarizability67.63 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+0.9709
Caco-2 permeable+0.7297
P-glycoprotein substrateSubstrate0.6692
P-glycoprotein inhibitor IInhibitor0.6415
P-glycoprotein inhibitor IIInhibitor0.5314
Renal organic cation transporterNon-inhibitor0.8248
CYP450 2C9 substrateNon-substrate0.7902
CYP450 2D6 substrateNon-substrate0.8958
CYP450 3A4 substrateSubstrate0.6873
CYP450 1A2 substrateNon-inhibitor0.8287
CYP450 2C9 inhibitorNon-inhibitor0.8072
CYP450 2D6 inhibitorNon-inhibitor0.9151
CYP450 2C19 inhibitorInhibitor0.5344
CYP450 3A4 inhibitorNon-inhibitor0.8284
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.542
Ames testNon AMES toxic0.9253
CarcinogenicityNon-carcinogens0.8829
BiodegradationNot ready biodegradable0.9891
Rat acute toxicity1.7534 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.876
hERG inhibition (predictor II)Non-inhibitor0.617
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 steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Estrane steroids / 17-oxosteroids / Phenanthrenes and derivatives / Tetralins / Ketones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Steroid ester / Estrane-skeleton / 17-oxosteroid / Oxosteroid / Phenanthrene / Tetralin / Benzenoid / Ketone / Carboxylic acid ester / Carboxylic acid derivative
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Drug created on October 20, 2007 04:27 / Updated on November 02, 2018 06:06