Ethynodiol diacetate (CED0013264)

Record Information
Version1.0
Creation Date2016-05-22 03:27:01 UTC
Update Date2026-08-22 03:59:56 UTC
Accession NumberCHEM016309
Identification
Common NameEthynodiol diacetate
ClassSmall Molecule
Description
Ethynodiol diacetate is an organic compound with the chemical formula C24H32O4 and an average molecular weight of 384.51 g/mol. Ethynodiol diacetate belongs to the steroid esters, a subclass of steroids and steroid derivatives within the organic compounds. It is further categorized under the superclass of lipids and lipid-like molecules. The compound is identified as an agonist of two protein targets: the progesterone receptor (PGR) and the estrogen receptor (ESR1). Ethynodiol diacetate has been found in or released from 22 recorded sources across several categories. Within electrical and electronic equipment, it is associated with antennas, amplifiers, electric switches, electrically stimulated smoking devices, and conductors or conductive bodies characterized by the conductive materials. In the realm of food, food processing and cookware, it is linked to processing meats, processing fish, food preservation, and fermentation processes for beer. Additionally, the compound is recorded in household cleaning and consumer products, specifically within tobacco smoke filters, non-electric simulated smoking devices, cigar cigarettes, and perfumes within detergents and soaps. Finally, it has been identified in building and construction sources, specifically ladders.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetateChEBI
17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetateChEBI
17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetateChEBI
17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetateChEBI
19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetateChEBI
3beta, 17beta-Diacetoxy-17alpha-ethynyl-4-oestreneChEBI
3beta,17beta-Diacetoxy-19-nor-17alpha-pregn-4-en-20-yneChEBI
17a-Ethynyl-19-norandrost-4-ene-3b,17-b-diol diacetateGenerator
17a-Ethynyl-19-norandrost-4-ene-3b,17-b-diol diacetic acidGenerator
17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetic acidGenerator
17Α-ethynyl-19-norandrost-4-ene-3β,17-β-diol diacetateGenerator
17Α-ethynyl-19-norandrost-4-ene-3β,17-β-diol diacetic acidGenerator
17a-Ethynyl-3,17-dihydroxy-4-estrene diacetateGenerator
17a-Ethynyl-3,17-dihydroxy-4-estrene diacetic acidGenerator
17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetic acidGenerator
17Α-ethynyl-3,17-dihydroxy-4-estrene diacetateGenerator
17Α-ethynyl-3,17-dihydroxy-4-estrene diacetic acidGenerator
17a-Ethynyl-4-estrene-3b,17b-diol diacetateGenerator
17a-Ethynyl-4-estrene-3b,17b-diol diacetic acidGenerator
17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetic acidGenerator
17Α-ethynyl-4-estrene-3β,17β-diol diacetateGenerator
17Α-ethynyl-4-estrene-3β,17β-diol diacetic acidGenerator
17a-Ethynylestr-4-ene-3b,17b-diol acetateGenerator
17a-Ethynylestr-4-ene-3b,17b-diol acetic acidGenerator
17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetic acidGenerator
17Α-ethynylestr-4-ene-3β,17β-diol acetateGenerator
17Α-ethynylestr-4-ene-3β,17β-diol acetic acidGenerator
19-Nor-17a-pregn-4-en-20-yne-3b,17-diol diacetateGenerator
19-Nor-17a-pregn-4-en-20-yne-3b,17-diol diacetic acidGenerator
19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetic acidGenerator
19-Nor-17α-pregn-4-en-20-yne-3β,17-diol diacetateGenerator
19-Nor-17α-pregn-4-en-20-yne-3β,17-diol diacetic acidGenerator
3b, 17b-Diacetoxy-17a-ethynyl-4-oestreneGenerator
3Β, 17β-diacetoxy-17α-ethynyl-4-oestreneGenerator
3b,17b-Diacetoxy-19-nor-17a-pregn-4-en-20-yneGenerator
3Β,17β-diacetoxy-19-nor-17α-pregn-4-en-20-yneGenerator
Ethynodiol diacetic acidGenerator
Ethinodiol diacetateHMDB
EthynodiolHMDB
EtynodiolHMDB
Ethyndiol diacetateHMDB
Diacetate, ethyndiolHMDB
Ethynodiol diacetate, (17 alpha)-isomerHMDB
FemulenHMDB
ContinuinHMDB
(3 beta, 17 alpha)-19-Norpregn-4-en-20-yne-3,17 diol diacetateHMDB
Diacetate, ethynodiolHMDB
Chemical FormulaC24H32O4
Average Molecular Mass384.509 g/mol
Monoisotopic Mass384.230 g/mol
CAS Registry Number297-76-7
IUPAC Name(1S,2R,5S,10R,11S,14R,15S)-5-(acetyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate
Traditional Nameethynodiol diacetate
SMILES[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CC[C@H](OC(C)=O)C=C3CC[C@@]21[H]
InChI IdentifierInChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
InChI KeyONKUMRGIYFNPJW-KIEAKMPYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Estrane-skeleton
  • Delta-4-steroid
  • Ynone
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Acetylide
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • terminal acetylenic compound (CHEBI:31580 )
  • steroid ester (CHEBI:31580 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C12724 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030124 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP3.99ALOGPS
logP3.69ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.62 m³·mol⁻¹ChemAxon
Polarizability44.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0100-1194000000-36378317102183460faeNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002u-0019000000-a73cd21b30c9439d33beNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004l-0079000000-136800a52b34f352d78eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00e9-0290000000-2ea658e56bd9ec1ef885Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-0009000000-85f53cde1cbdf66e3366Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-2029000000-0187f016d0d4a58f5182Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052e-7094000000-0495ab26817d2a5560a9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-0095000000-0d85902c71bc8262416eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fr-0193000000-f41b8945f2b34a40a819Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-3940000000-741355bc9568273bd065Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0029000000-4a30e3513b9cdfbc7e7dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-053s-4091000000-8176c0956e97e17ec13cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016u-2029000000-e5afd8ca7c979d5debd7Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2357.0Log mg/kg[1300:4200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
498LaddersBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
532SelectorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
649Pins ClothesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)4.12601
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)0.934191
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)135.769
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)12.378
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)29.1156
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)48.8115
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)118.642
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)45.3861
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)439.147
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)132.733
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)1604.94
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)130.865
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)24.7561
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)65.0041
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)3950.69
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)716.213
Click to view 3D structureAndrogen receptorP19091Mus musculusPredicted (SEA)37.1341
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)2404.06
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)3283.37
Click to view 3D structureTransient receptor potential cation channel subfamily M member 2E9PTA2Rattus norvegicusPredicted (SEA)4.82665
Steryl-sulfatase structureClick to view 3D structureSteryl-sulfataseP08842HumansPredicted (SEA)23.0434
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)3765.72
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)450.825
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)3881.25
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)50.8355
Concentrations
Not Available
External Links
DrugBank IDDB00823
HMDB IDHMDB0014961
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEthynodiol_Diacetate
Chemspider ID8913
ChEBI ID31580
PubChem Compound ID9270
Kegg Compound IDC12724
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM