Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:48 UTC |
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HMDB ID | HMDB0014961 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ethynodiol Diacetate |
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Description | Ethynodiol Diacetate is only found in individuals that have used or taken this drug. It is a synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive. [PubChem]Binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Ethynodiol Diacetate will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. |
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Structure | [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=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 |
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Synonyms | Value | Source |
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17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetate | ChEBI | 17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate | ChEBI | 17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetate | ChEBI | 17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetate | ChEBI | 19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetate | ChEBI | 3beta, 17beta-Diacetoxy-17alpha-ethynyl-4-oestrene | ChEBI | 3beta,17beta-Diacetoxy-19-nor-17alpha-pregn-4-en-20-yne | ChEBI | 17a-Ethynyl-19-norandrost-4-ene-3b,17-b-diol diacetate | Generator | 17a-Ethynyl-19-norandrost-4-ene-3b,17-b-diol diacetic acid | Generator | 17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetic acid | Generator | 17Α-ethynyl-19-norandrost-4-ene-3β,17-β-diol diacetate | Generator | 17Α-ethynyl-19-norandrost-4-ene-3β,17-β-diol diacetic acid | Generator | 17a-Ethynyl-3,17-dihydroxy-4-estrene diacetate | Generator | 17a-Ethynyl-3,17-dihydroxy-4-estrene diacetic acid | Generator | 17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetic acid | Generator | 17Α-ethynyl-3,17-dihydroxy-4-estrene diacetate | Generator | 17Α-ethynyl-3,17-dihydroxy-4-estrene diacetic acid | Generator | 17a-Ethynyl-4-estrene-3b,17b-diol diacetate | Generator | 17a-Ethynyl-4-estrene-3b,17b-diol diacetic acid | Generator | 17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetic acid | Generator | 17Α-ethynyl-4-estrene-3β,17β-diol diacetate | Generator | 17Α-ethynyl-4-estrene-3β,17β-diol diacetic acid | Generator | 17a-Ethynylestr-4-ene-3b,17b-diol acetate | Generator | 17a-Ethynylestr-4-ene-3b,17b-diol acetic acid | Generator | 17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetic acid | Generator | 17Α-ethynylestr-4-ene-3β,17β-diol acetate | Generator | 17Α-ethynylestr-4-ene-3β,17β-diol acetic acid | Generator | 19-Nor-17a-pregn-4-en-20-yne-3b,17-diol diacetate | Generator | 19-Nor-17a-pregn-4-en-20-yne-3b,17-diol diacetic acid | Generator | 19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetic acid | Generator | 19-Nor-17α-pregn-4-en-20-yne-3β,17-diol diacetate | Generator | 19-Nor-17α-pregn-4-en-20-yne-3β,17-diol diacetic acid | Generator | 3b, 17b-Diacetoxy-17a-ethynyl-4-oestrene | Generator | 3Β, 17β-diacetoxy-17α-ethynyl-4-oestrene | Generator | 3b,17b-Diacetoxy-19-nor-17a-pregn-4-en-20-yne | Generator | 3Β,17β-diacetoxy-19-nor-17α-pregn-4-en-20-yne | Generator | Ethynodiol diacetic acid | Generator | Ethinodiol diacetate | HMDB | Ethynodiol | HMDB | Etynodiol | HMDB | Ethyndiol diacetate | HMDB | Diacetate, ethyndiol | HMDB | Ethynodiol diacetate, (17 alpha)-isomer | HMDB | Femulen | HMDB | Continuin | HMDB | (3 beta, 17 alpha)-19-Norpregn-4-en-20-yne-3,17 diol diacetate | HMDB | Diacetate, ethynodiol | HMDB |
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Chemical Formula | C24H32O4 |
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Average Molecular Weight | 384.5085 |
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Monoisotopic Molecular Weight | 384.230059512 |
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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 |
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Traditional Name | ethynodiol diacetate |
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CAS Registry Number | 297-76-7 |
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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] |
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InChI Identifier | InChI=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 |
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InChI Key | ONKUMRGIYFNPJW-KIEAKMPYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroid esters |
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Direct Parent | Steroid esters |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic homopolycyclic compounds |
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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 )
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.004 g/L | Not Available | LogP | 5 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Ethynodiol Diacetate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0100-1194000000-36378317102183460fae | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethynodiol Diacetate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 10V, Negative-QTOF | splash10-000x-0009000000-85f53cde1cbdf66e3366 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 20V, Negative-QTOF | splash10-000x-2029000000-0187f016d0d4a58f5182 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 40V, Negative-QTOF | splash10-052e-7094000000-0495ab26817d2a5560a9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 10V, Negative-QTOF | splash10-001i-0029000000-4a30e3513b9cdfbc7e7d | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 20V, Negative-QTOF | splash10-053s-4091000000-8176c0956e97e17ec13c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 40V, Negative-QTOF | splash10-016u-2029000000-e5afd8ca7c979d5debd7 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 10V, Positive-QTOF | splash10-002u-0019000000-a73cd21b30c9439d33be | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 20V, Positive-QTOF | splash10-004l-0079000000-136800a52b34f352d78e | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 40V, Positive-QTOF | splash10-00e9-0290000000-2ea658e56bd9ec1ef885 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 10V, Positive-QTOF | splash10-016r-0095000000-0d85902c71bc8262416e | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 20V, Positive-QTOF | splash10-03fr-0193000000-f41b8945f2b34a40a819 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 40V, Positive-QTOF | splash10-0006-3940000000-741355bc9568273bd065 | 2021-10-11 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00823 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00823 | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00823 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 8913 |
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KEGG Compound ID | C12724 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Ethynodiol_Diacetate |
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METLIN ID | Not Available |
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PubChem Compound | 9270 |
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PDB ID | Not Available |
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ChEBI ID | 31580 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- 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. [PubMed:16902246 ]
- 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. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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