Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-08-31 18:39:04 UTC |
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Update Date | 2021-09-26 22:48:58 UTC |
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HMDB ID | HMDB0242496 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | (20R)-17,20-Dihydroxypregn-4-en-3-one |
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Description | (20R)-17,20-Dihydroxypregn-4-en-3-one, also known as 4-pregnene-17a,20b-diol-3-one or 17-DHP, 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 very few articles have been published on (20R)-17,20-Dihydroxypregn-4-en-3-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (20r)-17,20-dihydroxypregn-4-en-3-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (20R)-17,20-Dihydroxypregn-4-en-3-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | CC(O)C1(O)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC12C 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 |
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Synonyms | Value | Source |
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4-Pregnene-17a,20b-diol-3-one | HMDB | 4-Pregnene-17α,20β-diol-3-one | HMDB | 17-DHP | HMDB | 17,20beta-Dihydroxypregn-4-en-3-one | HMDB | 17 alpha,20 beta-Dihydroxypregn-4-en-3-one | HMDB | 17 alpha,20 beta-Dihydroxyprogesterone | HMDB | 17alpha-Hydroxy-20beta-dihydroprogesterone | HMDB |
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Chemical Formula | C21H32O3 |
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Average Molecular Weight | 332.484 |
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Monoisotopic Molecular Weight | 332.23514489 |
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IUPAC Name | 14-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 | 14-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)C1(O)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC12C |
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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 |
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InChI Key | MASCESDECGBIBB-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
- 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 | |
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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 IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(20R)-17,20-Dihydroxypregn-4-en-3-one,2TMS,isomer #1 | CC(O[Si](C)(C)C)C1(O[Si](C)(C)C)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC21C | 3113.5 | Semi standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TMS,isomer #1 | CC(O[Si](C)(C)C)C1(O[Si](C)(C)C)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC21C | 2977.2 | Standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TMS,isomer #1 | CC(O[Si](C)(C)C)C1(O[Si](C)(C)C)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC21C | 3195.5 | Standard polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TMS,isomer #3 | CC(O)C1(O[Si](C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC21C | 2970.0 | Semi standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TMS,isomer #3 | CC(O)C1(O[Si](C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC21C | 3038.0 | Standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TMS,isomer #3 | CC(O)C1(O[Si](C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC21C | 3261.1 | Standard polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,3TMS,isomer #1 | CC(O[Si](C)(C)C)C1(O[Si](C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC21C | 2973.5 | Semi standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,3TMS,isomer #1 | CC(O[Si](C)(C)C)C1(O[Si](C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC21C | 3032.4 | Standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,3TMS,isomer #1 | CC(O[Si](C)(C)C)C1(O[Si](C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C)=CCC4(C)C3CCC21C | 3193.8 | Standard polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,1TBDMS,isomer #2 | CC(O)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC21C | 3301.1 | Semi standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,1TBDMS,isomer #2 | CC(O)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC21C | 3291.6 | Standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,1TBDMS,isomer #2 | CC(O)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC21C | 3359.1 | Standard polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC21C | 3596.7 | Semi standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC21C | 3547.9 | Standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC21C | 3429.4 | Standard polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #2 | CC(O[Si](C)(C)C(C)(C)C)C1(O)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC21C | 3464.1 | Semi standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #2 | CC(O[Si](C)(C)C(C)(C)C)C1(O)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC21C | 3531.9 | Standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #2 | CC(O[Si](C)(C)C(C)(C)C)C1(O)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC21C | 3506.2 | Standard polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #3 | CC(O)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC21C | 3477.1 | Semi standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #3 | CC(O)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC21C | 3521.0 | Standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #3 | CC(O)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC21C | 3485.3 | Standard polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,3TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC21C | 3718.2 | Semi standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,3TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC21C | 3732.9 | Standard non polar | 33892256 | (20R)-17,20-Dihydroxypregn-4-en-3-one,3TBDMS,isomer #1 | CC(O[Si](C)(C)C(C)(C)C)C1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4(C)C3CCC21C | 3462.6 | Standard 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 - (20R)-17,20-Dihydroxypregn-4-en-3-one GC-MS (Non-derivatized) - 70eV, Positive | splash10-0zfu-2298000000-e0451384f417ced62bbd | 2021-09-23 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-03 | 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 - (20R)-17,20-Dihydroxypregn-4-en-3-one 10V, Positive-QTOF | splash10-00lr-0009000000-701b0f43938bf417c0a2 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one 20V, Positive-QTOF | splash10-000w-0695000000-3221706f39b025d56e1a | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one 40V, Positive-QTOF | splash10-052f-5900000000-bb914c5b38d8fb6ba1bb | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one 10V, Negative-QTOF | splash10-001i-0009000000-1861adb28442bc6eb9c2 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one 20V, Negative-QTOF | splash10-00kr-0092000000-b68b38a389fab0733411 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (20R)-17,20-Dihydroxypregn-4-en-3-one 40V, Negative-QTOF | splash10-00li-0090000000-67175fe844998f40e20c | 2021-10-12 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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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 | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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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 | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 543392 |
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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 | 625529 |
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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 | - Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]
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