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 15:16:52 UTC |
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Update Date | 2022-03-07 02:52:02 UTC |
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HMDB ID | HMDB0015579 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Quinestrol |
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Description | Quinestrol is only found in individuals that have used or taken this drug. It is a 3-cyclopentyl ether of ethinyl estradiol.Estrogens diffuse into their target cells and interact with a protein receptor (the estrogen receptor). Estrogen interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH). |
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Structure | [H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC1CCCC1)C=C3 InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1 |
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Synonyms | Value | Source |
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17-alpha-Ethinylestradiol 3-cyclopentyl ether | ChEBI | 17alpha-Ethynylestradiol 3-cyclopentyl ether | ChEBI | Eston | ChEBI | Estradiol-17-beta 3-cyclopentyl ether | ChEBI | Estrovis | ChEBI | Estrovis 4000 | ChEBI | Estrovister | ChEBI | Plestrovis | ChEBI | Quilea | ChEBI | Quinestrolum | ChEBI | 17-a-Ethinylestradiol 3-cyclopentyl ether | Generator | 17-Α-ethinylestradiol 3-cyclopentyl ether | Generator | 17a-Ethynylestradiol 3-cyclopentyl ether | Generator | 17Α-ethynylestradiol 3-cyclopentyl ether | Generator | Estradiol-17-b 3-cyclopentyl ether | Generator | Estradiol-17-β 3-cyclopentyl ether | Generator | Quinestrolo | HMDB | Ethinyl estradiol 3 cyclopentyl ether | HMDB | Parke davis brand OF quinestrol | HMDB | Ethinyl estradiol 3-cyclopentyl ether | HMDB |
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Chemical Formula | C25H32O2 |
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Average Molecular Weight | 364.5204 |
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Monoisotopic Molecular Weight | 364.240230268 |
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IUPAC Name | (1S,10R,11S,14R,15S)-5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol |
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Traditional Name | quinestrol |
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CAS Registry Number | 152-43-2 |
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SMILES | [H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC1CCCC1)C=C3 |
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InChI Identifier | InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1 |
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InChI Key | PWZUUYSISTUNDW-VAFBSOEGSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton. |
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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 | Estrane steroids |
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Direct Parent | Estrane steroids |
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Alternative Parents | |
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Substituents | - Estrane-skeleton
- Hydroxysteroid
- 17-hydroxysteroid
- Phenanthrene
- Tetralin
- Alkyl aryl ether
- Benzenoid
- Ynone
- Tertiary alcohol
- Cyclic alcohol
- Ether
- Acetylide
- Organooxygen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | |
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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 | |
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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 | 107.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0016 g/L | Not Available | LogP | Not Available | 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 IndicesUnderivatizedDerivatized | 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 - Quinestrol GC-MS (Non-derivatized) - 70eV, Positive | splash10-001a-1398000000-24b78cbc71e43f9b5f86 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Quinestrol GC-MS (1 TMS) - 70eV, Positive | splash10-05fr-2165900000-781ffc739b80bdecd9f6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Quinestrol 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Quinestrol , positive-QTOF | splash10-0a59-2920000000-99119dee5db3aab05906 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 10V, Positive-QTOF | splash10-014i-3119000000-c081ebe349df6500cce1 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 20V, Positive-QTOF | splash10-014i-5679000000-083b5505ec8847453fb6 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 40V, Positive-QTOF | splash10-0aor-9010000000-61cd144aeff30afa3d84 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 10V, Negative-QTOF | splash10-03di-1019000000-53e9c20e422b817daeee | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 20V, Negative-QTOF | splash10-03di-2039000000-98c7bde745c0bb0f0c66 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 40V, Negative-QTOF | splash10-00n4-4090000000-126f2b3e60f8f02ea9a6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 10V, Positive-QTOF | splash10-014i-0029000000-870248767e5db586d1c8 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 20V, Positive-QTOF | splash10-016s-0697000000-91630dbd68fc65dfab8d | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 40V, Positive-QTOF | splash10-02ta-3982000000-2ce057537d39e23423a6 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 10V, Negative-QTOF | splash10-03di-0009000000-d9a39c9613d3a865070c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 20V, Negative-QTOF | splash10-03di-0009000000-db0674397e8613b10789 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quinestrol 40V, Negative-QTOF | splash10-0udi-0095000000-c05b7d0ae8d2055690d0 | 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 DB04575 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB04575 | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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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 | DB04575 |
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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 | 8694 |
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KEGG Compound ID | C07619 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Quinestrol |
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METLIN ID | Not Available |
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PubChem Compound | 9046 |
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PDB ID | Not Available |
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ChEBI ID | 8716 |
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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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