Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 18:41:33 UTC |
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Update Date | 2022-03-07 02:53:54 UTC |
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HMDB ID | HMDB0033918 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one |
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Description | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Based on a literature review a significant number of articles have been published on (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one. |
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Structure | CC(O)C1CC(O)C2C3CCC4=CC(=O)CCC4(C)C3CCC12C InChI=1S/C21H32O3/c1-12(22)17-11-18(24)19-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h10,12,15-19,22,24H,4-9,11H2,1-3H3 |
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Synonyms | Value | Source |
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(15a,20R)-15,20-Dihydroxypregn-4-en-3-one | Generator | (15Α,20R)-15,20-dihydroxypregn-4-en-3-one | Generator |
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Chemical Formula | C21H32O3 |
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Average Molecular Weight | 332.477 |
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Monoisotopic Molecular Weight | 332.23514489 |
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IUPAC Name | 12-hydroxy-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one |
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Traditional Name | 12-hydroxy-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one |
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CAS Registry Number | Not Available |
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SMILES | CC(O)C1CC(O)C2C3CCC4=CC(=O)CCC4(C)C3CCC12C |
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InChI Identifier | InChI=1S/C21H32O3/c1-12(22)17-11-18(24)19-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h10,12,15-19,22,24H,4-9,11H2,1-3H3 |
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InChI Key | OVQSVMZESAVYPN-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. |
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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 | Pregnane steroids |
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Direct Parent | Gluco/mineralocorticoids, progestogins and derivatives |
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Alternative Parents | |
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Substituents | - Progestogin-skeleton
- 20-hydroxysteroid
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- Oxosteroid
- 15-hydroxysteroid
- Hydroxysteroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic alcohol
- Secondary alcohol
- Cyclic ketone
- Ketone
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- Alcohol
- Organic oxide
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic 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 | |
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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 | 132 - 134 °C | 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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(15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,1TMS,isomer #1 | CC(O[Si](C)(C)C)C1CC(O)C2C3CCC4=CC(=O)CCC4(C)C3CCC12C | 3095.9 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,1TMS,isomer #2 | CC(O)C1CC(O[Si](C)(C)C)C2C3CCC4=CC(=O)CCC4(C)C3CCC12C | 3107.5 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,1TMS,isomer #3 | CC(O)C1CC(O)C2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C | 3010.7 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,2TMS,isomer #1 | CC(O[Si](C)(C)C)C1CC(O[Si](C)(C)C)C2C3CCC4=CC(=O)CCC4(C)C3CCC12C | 3121.3 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,2TMS,isomer #2 | CC(O[Si](C)(C)C)C1CC(O)C2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C | 3040.8 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,2TMS,isomer #3 | CC(O)C1CC(O[Si](C)(C)C)C2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C | 3038.3 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,3TMS,isomer #1 | CC(O[Si](C)(C)C)C1CC(O[Si](C)(C)C)C2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C | 2958.8 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,3TMS,isomer #1 | CC(O[Si](C)(C)C)C1CC(O[Si](C)(C)C)C2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC12C | 3044.7 | Standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,1TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)C1CC(O)C2C3CCC4=CC(=O)CCC4(C)C3CCC12C | 3345.6 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,1TBDMS,isomer #2 | CC(O)C1CC(O[Si](C)(C)C(C)(C)C)C2C3CCC4=CC(=O)CCC4(C)C3CCC12C | 3351.1 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,1TBDMS,isomer #3 | CC(O)C1CC(O)C2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C | 3250.5 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)C1CC(O[Si](C)(C)C(C)(C)C)C2C3CCC4=CC(=O)CCC4(C)C3CCC12C | 3591.6 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #2 | CC(O[Si](C)(C)C(C)(C)C)C1CC(O)C2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C | 3512.8 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #3 | CC(O)C1CC(O[Si](C)(C)C(C)(C)C)C2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C | 3494.3 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,3TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)C1CC(O[Si](C)(C)C(C)(C)C)C2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C | 3640.1 | Semi standard non polar | 33892256 | (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one,3TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)C1CC(O[Si](C)(C)C(C)(C)C)C2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC12C | 3772.3 | 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 - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one GC-MS (Non-derivatized) - 70eV, Positive | splash10-029i-1294000000-d185512dbebaeae952b9 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one GC-MS (2 TMS) - 70eV, Positive | splash10-03di-2313900000-042cfa6697a1fafeb411 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 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 - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 10V, Positive-QTOF | splash10-0159-0049000000-0000572e3f131251db72 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 20V, Positive-QTOF | splash10-014j-0395000000-7da40c110392df0b64a7 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 40V, Positive-QTOF | splash10-052e-0590000000-59e4a8cb610ccc6a32e3 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 10V, Negative-QTOF | splash10-001i-0019000000-6d2b33cd4b067c542e7b | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 20V, Negative-QTOF | splash10-01q9-0039000000-b643883f66448c0437df | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 40V, Negative-QTOF | splash10-00ku-1093000000-b5f5bf155b27d5da4708 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 10V, Negative-QTOF | splash10-001i-0019000000-3d48d03153e0762a8c96 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 20V, Negative-QTOF | splash10-01q9-0039000000-1cd6b61e4a1bd813ceeb | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 40V, Negative-QTOF | splash10-00kr-0092000000-bd0dac4511ff5245c7dd | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 10V, Positive-QTOF | splash10-00lr-0019000000-daab8fa283d37b415de2 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 20V, Positive-QTOF | splash10-00ls-0294000000-731ffa1f37611a7ffb07 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (15alpha,20R)-15,20-Dihydroxypregn-4-en-3-one 40V, Positive-QTOF | splash10-052f-3940000000-4ade5231e4baac5e0ac7 | 2021-09-25 | 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 | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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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 | FDB012116 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 9920329 |
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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 | 77963611 |
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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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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