Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 20:35:28 UTC |
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Update Date | 2016-11-09 01:22:15 UTC |
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Accession Number | CHEM040387 |
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Identification |
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Common Name | 17-alpha,20-alpha-Dihydroxypregn-4-en-3-one |
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Class | Small Molecule |
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Description | The (20S)-stereoisomer of 17,20-dihydroxypregn-4-en-3-one. |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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17a,20a-Dihydroxypregn-4-en-3-one | Generator | 17Α,20α-dihydroxypregn-4-en-3-one | Generator | 17alpha,20alpha-Dihydroxypregn-4-en-3-one | ChEBI | 17-a,20-a-Dihydroxypregn-4-en-3-one | Generator, HMDB | 17-α,20-α-dihydroxypregn-4-en-3-one | Generator, HMDB | (20S)-17,20-Dihydroxypregn-4-en-3-one | HMDB | 17 alpha, 20 alpha-OHP | HMDB | 17 alpha, 20 alpha-P | HMDB | 17,20 alpha-OHP | HMDB | 17-alpha,20-alpha-Dihydroxypregn-4-en-3-one | HMDB | 4-Pregnen-17a, 20a-diol-3-one | HMDB | 4-Pregnen-17α, 20α-diol-3-one | HMDB | 4-Pregnen-17alpha, 20alpha-diol-3-one | HMDB | 17a-Hydroxy-20a-dihydroprogesterone | HMDB | 17α-Hydroxy-20α-dihydroprogesterone | HMDB | 17alpha-Hydroxy-20alpha-dihydroprogesterone | HMDB | 20a-Dihydroxyprogesterone | HMDB | 20α-Dihydroxyprogesterone | HMDB | 20alpha-Dihydroxyprogesterone | HMDB | 17,20α-Dihydroxy-4-pregnen-3-one | HMDB | 17,20a-Dihydroxy-4-pregnen-3-one | HMDB | 17,20alpha-Dihydroxy-4-pregnen-3-one | HMDB | 17,20α-Dihydroxy-pregn-4-en-3-one | HMDB | 17,20a-Dihydroxy-pregn-4-en-3-one | HMDB | 17,20alpha-Dihydroxy-pregn-4-en-3-one | HMDB | 17α,20α-Dihydroxy-4-pregnen-3-one | HMDB | 17a,20a-Dihydroxy-4-pregnen-3-one | HMDB | 17alpha,20alpha-Dihydroxy-4-pregnen-3-one | HMDB | 17α,20α-Dihydroxypregn-4-ene-3-one | HMDB | 17a,20a-Dihydroxypregn-4-ene-3-one | HMDB | 17alpha,20alpha-Dihydroxypregn-4-ene-3-one | HMDB | 17α,20α-Dihydroxyprogesterone | HMDB | 17a,20a-Dihydroxyprogesterone | HMDB | 17alpha,20alpha-Dihydroxyprogesterone | HMDB | Pregn-4-ene-17α,20α-diol-3-one | HMDB | Pregn-4-ene-17a,20a-diol-3-one | HMDB | Pregn-4-ene-17alpha,20alpha-diol-3-one | HMDB |
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Chemical Formula | C21H32O3 |
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Average Molecular Mass | 332.477 g/mol |
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Monoisotopic Mass | 332.235 g/mol |
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CAS Registry Number | 652-69-7 |
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IUPAC Name | (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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Traditional Name | (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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SMILES | [H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C |
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InChI Identifier | InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12-13,16-18,22,24H,4-11H2,1-3H3/t13-,16+,17-,18-,19-,20-,21-/m0/s1 |
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InChI Key | MASCESDECGBIBB-HNXXTFFGSA-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
- 17-hydroxysteroid
- Oxosteroid
- Hydroxysteroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic alcohol
- Tertiary alcohol
- 1,2-diol
- Cyclic ketone
- Secondary alcohol
- Ketone
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | - 17,20-dihydroxypregn-4-en-3-one (CHEBI:16418 )
- C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030183 )
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-1009-3389000000-cb7be02bfc7f8d750db9 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-03di-2221900000-4d8859515388ae586c48 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lr-0029000000-4a1c28efa846463a0725 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05nb-0296000000-5f113d14e04b9e53fe21 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00r5-2591000000-c29c05785ba6023d6c32 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0019000000-9163bb555789226a64c8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001r-0097000000-6fd6b47c5cef917bc228 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05tr-0091000000-a0583d76ae6c45c3876f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0019000000-dc49633d891cfa3ca389 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0400-0900000000-0bdc7df8e969edc68b24 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-072a-2920000000-c955f907f75e91d61e53 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0019000000-3d48d03153e0762a8c96 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001r-0098000000-2ed26b3a398241f5362e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014r-0090000000-926949293e5e1b71b18e | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0011653 |
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FooDB ID | FDB028344 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | 17-ALPHA20-ALPHA-DIHYDROXYPREGN-4-EN-3- |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 389326 |
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ChEBI ID | 16418 |
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PubChem Compound ID | 440368 |
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Kegg Compound ID | C04518 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Mahajan DK, Anderson G, Poole WK, Billiar RB, Little B: Changes in the concentration of 17 alpha,20 alpha-dihydroxypregn-4-en-3-one during pregnancy, labor, and delivery and the effect of dexamethasone treatment during the third trimester of pregnancy. J Clin Endocrinol Metab. 1983 Sep;57(3):585-91. | 2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. | 3. 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. | 4. 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. | 5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. | 6. Schenken RS, Williams RF, Hodgen GD: Effect of 20 alpha-dihydroxyprogesterone on the estrogen-induced bioactive luteinizing hormone surge in ovariectomized monkeys. Fertil Steril. 1990 Dec;54(6):1146-9. | 7. The lipid handbook with CD-ROM |
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