NAV

Oleoyl-estrone

Identification

Generic Name
Oleoyl-estrone
DrugBank Accession Number
DB04870
Background

Oleoyl-estrone (OE) is a fatty acid ester of estrone. This hormone occurs naturally and is found circulating in various animal species and humans. It has been shown in animal studies to promote the loss of body fat while maintaining body protein storage, maintaining nitrogen balance. Body protein loss is an unpleasant effect of fat loss by the restriction of calories, and studies show that this drug appears to avoid this effect.

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 534.8122
Monoisotopic: 534.407295594
Chemical Formula
C36H54O3
Synonyms
  • Estrone 3-oleate
  • Estrone monooleate
  • Estrone oleic acid ester
  • OE
  • Oleoyl estrone
  • Oleoylestrone
External IDs
  • MP-101
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Pharmacology

Indication

For the treatment of obesity.

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
Chemical TaxonomyProvided by Classyfire
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
17-oxosteroid / Aromatic homopolycyclic compound / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Estrane-skeleton / Hydrocarbon derivative / Ketone / Monocarboxylic acid or derivatives
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
64R56KMG1Z
CAS number
180003-17-2
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
(3aS,3bR,9bS,11aS)-11a-methyl-1-oxo-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-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

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. [Article]
  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. [Article]
PubChem Compound
6918373
PubChem Substance
175426878
ChemSpider
5293576
ZINC
ZINC000014300189
Wikipedia
Oleoyl-estrone

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3WithdrawnTreatmentSBS / Short Bowel Syndrome (SBS) / Short Gut / Short Gut Syndrome1
2TerminatedTreatmentAggression / Agitation / Dementia / Dementia of the Alzheimer's Type / Psychosis1
2Unknown StatusTreatmentObesity2
Not AvailableRecruitingSupportive CareCoronavirus Disease 2019 (COVID‑19)1

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 Basic)-7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area43.37 Å2Chemaxon
Rotatable Bond Count17Chemaxon
Refractivity162.99 m3·mol-1Chemaxon
Polarizability67.61 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/MSsplash10-014s-6392070000-5b76738cd398ff341ec3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0060090000-c434d856dbfcdce09957
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lr-0091150000-54ab3487600478bcd3b8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00y0-9470130000-8b328af04c14e32c5d01
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uxr-2092020000-6a8c1caf661d5e1fa277
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dv-7941110000-ad2afe72ba8df62c64a9
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-259.1830116
predicted
DarkChem Lite v0.1.0
[M-H]-245.2488
predicted
DeepCCS 1.0 (2019)
[M+H]+259.4466116
predicted
DarkChem Lite v0.1.0
[M+H]+247.14421
predicted
DeepCCS 1.0 (2019)
[M+Na]+252.80424
predicted
DeepCCS 1.0 (2019)

Drug created at October 20, 2007 10:27 / Updated at June 12, 2020 16:52