Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-09 16:11:46 UTC |
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Update Date | 2021-09-14 15:19:03 UTC |
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HMDB ID | HMDB0060999 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-hydroxystradiol |
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Description | 4-hydroxystradiol is a metabolite of estradiol. Estradiol (E2 or 17β-estradiol, also oestradiol) is a sex hormone. Estradiol is abbreviated E2 as it has 2 hydroxyl groups in its molecular structure. Estrone has 1 (E1) and estriol has 3 (E3). Estradiol is about 10 times as potent as estrone and about 80 times as potent as estriol in its estrogenic effect. Except during the early follicular phase of the menstrual cycle, its serum levels are somewhat higher than that of estrone during the reproductive years of the human female. (Wikipedia) |
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Structure | CC12CCC3C(CCC4=C3C=CC(O)=C4O)C1CCC2O InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3 |
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Synonyms | Not Available |
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Chemical Formula | C18H24O3 |
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Average Molecular Weight | 288.3814 |
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Monoisotopic Molecular Weight | 288.172544634 |
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IUPAC Name | 15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,6,14-triol |
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Traditional Name | 15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,6,14-triol |
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CAS Registry Number | Not Available |
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SMILES | CC12CCC3C(CCC4=C3C=CC(O)=C4O)C1CCC2O |
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InChI Identifier | InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3 |
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InChI Key | QOZFCKXEVSGWGS-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. |
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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 | Estrogens and derivatives |
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Alternative Parents | |
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Substituents | - Estrogen-skeleton
- 3-hydroxysteroid
- 4-hydroxysteroid
- 17-hydroxysteroid
- Hydroxysteroid
- Phenanthrene
- Tetralin
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Cyclic alcohol
- Secondary alcohol
- Polyol
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Alcohol
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | Not Available |
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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 | Not Available |
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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 | Not Available | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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4-hydroxystradiol,1TMS,isomer #1 | CC12CCC3C4=CC=C(O[Si](C)(C)C)C(O)=C4CCC3C1CCC2O | 2847.2 | Semi standard non polar | 33892256 | 4-hydroxystradiol,1TMS,isomer #2 | CC12CCC3C4=CC=C(O)C(O[Si](C)(C)C)=C4CCC3C1CCC2O | 2827.1 | Semi standard non polar | 33892256 | 4-hydroxystradiol,1TMS,isomer #3 | CC12CCC3C4=CC=C(O)C(O)=C4CCC3C1CCC2O[Si](C)(C)C | 2851.1 | Semi standard non polar | 33892256 | 4-hydroxystradiol,2TMS,isomer #1 | CC12CCC3C4=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CCC2O | 2886.5 | Semi standard non polar | 33892256 | 4-hydroxystradiol,2TMS,isomer #2 | CC12CCC3C4=CC=C(O[Si](C)(C)C)C(O)=C4CCC3C1CCC2O[Si](C)(C)C | 2873.1 | Semi standard non polar | 33892256 | 4-hydroxystradiol,2TMS,isomer #3 | CC12CCC3C4=CC=C(O)C(O[Si](C)(C)C)=C4CCC3C1CCC2O[Si](C)(C)C | 2825.4 | Semi standard non polar | 33892256 | 4-hydroxystradiol,3TMS,isomer #1 | CC12CCC3C4=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CCC2O[Si](C)(C)C | 2854.5 | Semi standard non polar | 33892256 | 4-hydroxystradiol,1TBDMS,isomer #1 | CC12CCC3C4=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C4CCC3C1CCC2O | 3111.9 | Semi standard non polar | 33892256 | 4-hydroxystradiol,1TBDMS,isomer #2 | CC12CCC3C4=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C4CCC3C1CCC2O | 3086.0 | Semi standard non polar | 33892256 | 4-hydroxystradiol,1TBDMS,isomer #3 | CC12CCC3C4=CC=C(O)C(O)=C4CCC3C1CCC2O[Si](C)(C)C(C)(C)C | 3092.1 | Semi standard non polar | 33892256 | 4-hydroxystradiol,2TBDMS,isomer #1 | CC12CCC3C4=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C4CCC3C1CCC2O | 3359.1 | Semi standard non polar | 33892256 | 4-hydroxystradiol,2TBDMS,isomer #2 | CC12CCC3C4=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C4CCC3C1CCC2O[Si](C)(C)C(C)(C)C | 3334.6 | Semi standard non polar | 33892256 | 4-hydroxystradiol,2TBDMS,isomer #3 | CC12CCC3C4=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C4CCC3C1CCC2O[Si](C)(C)C(C)(C)C | 3289.1 | Semi standard non polar | 33892256 | 4-hydroxystradiol,3TBDMS,isomer #1 | CC12CCC3C4=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C4CCC3C1CCC2O[Si](C)(C)C(C)(C)C | 3495.3 | Semi standard non polar | 33892256 |
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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 - 4-hydroxystradiol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0adr-2490000000-3aa4258bafb58fa45700 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (3 TMS) - 70eV, Positive | splash10-002u-1002900000-9d2df63f119c9dbf0962 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_3_1) - 70eV, Positive | Not Available | 2021-11-05 | 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 - 4-hydroxystradiol 10V, Positive-QTOF | splash10-00dr-0090000000-ed24fd96ce297ed99b3a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 20V, Positive-QTOF | splash10-00dr-0690000000-235f4fdeb530ba151b7e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 40V, Positive-QTOF | splash10-000f-7590000000-d4d1f4c9d17256df8044 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 10V, Negative-QTOF | splash10-000i-0090000000-aff5ef70c0e417742016 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 20V, Negative-QTOF | splash10-000i-0090000000-e8909947f3f0e44912b2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 40V, Negative-QTOF | splash10-0a4l-0090000000-dc9ec3182d5ff0ec464a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 10V, Positive-QTOF | splash10-000i-0090000000-32753f11018f82a62c9f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 20V, Positive-QTOF | splash10-00di-1490000000-c7d5493bba66ead78048 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 40V, Positive-QTOF | splash10-0c0u-1910000000-66fc47ad3e4ee10ef0a0 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 10V, Negative-QTOF | splash10-000i-0090000000-843a74fabb1d0eb512a1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 20V, Negative-QTOF | splash10-000i-0090000000-3ec623049114707070fb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-hydroxystradiol 40V, Negative-QTOF | splash10-070i-0590000000-d07e02936cc84c7dc41e | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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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 | Normal | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | 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 | Not Available |
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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 | 1680 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 1743 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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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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