Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2019-04-02 21:57:33 UTC |
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Update Date | 2022-09-22 17:44:15 UTC |
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HMDB ID | HMDB0240313 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 4-Androsten-3beta,17beta-diol disulfate |
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Description | 4-Androsten-3beta,17beta-diol disulfate, also known as 4-androsten-3β,17β-diol disulfate, is classified as a member of the sulfated steroids. Sulfated steroids are sterol lipids containing a sulfate group attached to the steroid skeleton. 4-Androsten-3beta,17beta-diol disulfate is considered to be a practically insoluble (in water) and an extremely strong acidic compound. Human plasma levels of 4-androsten-3beta,17beta-diol disulfate were reported to be influenced by genetic variants in the gene SULT2A1 which codes for the enzyme dehydroepiandrosterone sulfotransferase (PMID: 24816252 ). |
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Structure | [H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@H](CC[C@]12C)OS(O)(=O)=O InChI=1S/C19H30O8S2/c1-18-9-7-13(26-28(20,21)22)11-12(18)3-4-14-15-5-6-17(27-29(23,24)25)19(15,2)10-8-16(14)18/h11,13-17H,3-10H2,1-2H3,(H,20,21,22)(H,23,24,25)/t13-,14-,15-,16-,17-,18-,19-/m0/s1 |
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Synonyms | Value | Source |
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(3beta,17beta)-Androst-4-ene-3,17-diyl bis(hydrogen sulfate) | ChEBI | (3b,17b)-Androst-4-ene-3,17-diyl bis(hydrogen sulfate) | Generator | (3b,17b)-Androst-4-ene-3,17-diyl bis(hydrogen sulfuric acid) | Generator | (3b,17b)-Androst-4-ene-3,17-diyl bis(hydrogen sulphate) | Generator | (3b,17b)-Androst-4-ene-3,17-diyl bis(hydrogen sulphuric acid) | Generator | (3beta,17beta)-Androst-4-ene-3,17-diyl bis(hydrogen sulfuric acid) | Generator | (3beta,17beta)-Androst-4-ene-3,17-diyl bis(hydrogen sulphate) | Generator | (3beta,17beta)-Androst-4-ene-3,17-diyl bis(hydrogen sulphuric acid) | Generator | (3Β,17β)-androst-4-ene-3,17-diyl bis(hydrogen sulfate) | Generator | (3Β,17β)-androst-4-ene-3,17-diyl bis(hydrogen sulfuric acid) | Generator | (3Β,17β)-androst-4-ene-3,17-diyl bis(hydrogen sulphate) | Generator | (3Β,17β)-androst-4-ene-3,17-diyl bis(hydrogen sulphuric acid) | Generator | 4-Androsten-3b,17b-diol disulfate | Generator | 4-Androsten-3b,17b-diol disulfuric acid | Generator | 4-Androsten-3b,17b-diol disulphate | Generator | 4-Androsten-3b,17b-diol disulphuric acid | Generator | 4-Androsten-3beta,17beta-diol disulfuric acid | Generator | 4-Androsten-3beta,17beta-diol disulphate | Generator | 4-Androsten-3beta,17beta-diol disulphuric acid | Generator | 4-Androsten-3β,17β-diol disulfate | Generator | 4-Androsten-3β,17β-diol disulfuric acid | Generator | 4-Androsten-3β,17β-diol disulphate | Generator | 4-Androsten-3β,17β-diol disulphuric acid | Generator | 4-Androstenediol disulfuric acid | HMDB | 4-Androstenediol disulphate | HMDB | 4-Androstenediol disulphuric acid | HMDB | 4-Androstene-3b,17b-diol disulfate | HMDB | 4-Androstene-3b,17b-diol disulfuric acid | HMDB | 4-Androstene-3b,17b-diol disulphate | HMDB | 4-Androstene-3b,17b-diol disulphuric acid | HMDB | 4-Androstene-3beta,17beta-diol disulfuric acid | HMDB | 4-Androstene-3beta,17beta-diol disulphate | HMDB | 4-Androstene-3beta,17beta-diol disulphuric acid | HMDB | 4-Androstene-3β,17β-diol disulfate | HMDB | 4-Androstene-3β,17β-diol disulfuric acid | HMDB | 4-Androstene-3β,17β-diol disulphate | HMDB | 4-Androstene-3β,17β-diol disulphuric acid | HMDB | 4-Androstene-3beta,17beta-diol disulfate | HMDB | Androst-4-en-3beta,17beta-ylene sulfate | HMDB | Androst-4-en-3beta,17beta-ylene sulphate | HMDB | Androst-4-en-3β,17β-ylene sulfate | HMDB | Androst-4-en-3β,17β-ylene sulphate | HMDB | Androst-4-ene-3beta,17beta-diol 3,17-disulfate | HMDB | Androst-4-ene-3beta,17beta-diol 3,17-disulphate | HMDB | Androst-4-ene-3β,17β-diol 3,17-disulfate | HMDB | Androst-4-ene-3β,17β-diol 3,17-disulphate | HMDB | Androstenediol disulfate | HMDB | Androstenediol disulphate | HMDB | 4-Androsten-3beta,17beta-diol disulfate | HMDB |
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Chemical Formula | C19H30O8S2 |
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Average Molecular Weight | 450.56 |
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Monoisotopic Molecular Weight | 450.138210274 |
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IUPAC Name | [(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]oxidanesulfonic acid |
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Traditional Name | [(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]oxidanesulfonic acid |
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CAS Registry Number | 1357147-18-2 |
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SMILES | [H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@H](CC[C@]12C)OS(O)(=O)=O |
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InChI Identifier | InChI=1S/C19H30O8S2/c1-18-9-7-13(26-28(20,21)22)11-12(18)3-4-14-15-5-6-17(27-29(23,24)25)19(15,2)10-8-16(14)18/h11,13-17H,3-10H2,1-2H3,(H,20,21,22)(H,23,24,25)/t13-,14-,15-,16-,17-,18-,19-/m0/s1 |
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InChI Key | UWPTUYJASNIIJM-LOVVWNRFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid 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 | Sulfated steroids |
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Direct Parent | Sulfated steroids |
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Alternative Parents | |
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Substituents | - Sulfated steroid skeleton
- Androstane-skeleton
- Delta-4-steroid
- Sulfuric acid ester
- Alkyl sulfate
- Sulfate-ester
- Sulfuric acid monoester
- Organic sulfuric acid or derivatives
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- 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 | 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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M-2H]- | 231.9 | 30932474 | DeepCCS | [M+Na]+ | 206.202 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C | 3573.1 | Semi standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C | 3508.2 | Standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C | 4766.7 | Standard polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #2 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O | 3563.3 | Semi standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #2 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O | 3498.4 | Standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #2 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O | 4749.1 | Standard polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,2TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C | 3577.4 | Semi standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,2TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C | 3707.3 | Standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,2TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C | 4647.6 | Standard polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C | 3794.8 | Semi standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C | 3816.7 | Standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C | 4879.8 | Standard polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 3800.2 | Semi standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 3822.3 | Standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 4853.7 | Standard polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 4016.5 | Semi standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 4312.8 | Standard non polar | 33892256 | 4-Androsten-3beta,17beta-diol disulfate,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 4757.9 | Standard polar | 33892256 |
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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-Androsten-3beta,17beta-diol disulfate 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 - 4-Androsten-3beta,17beta-diol disulfate 10V, Positive-QTOF | splash10-0udi-0019800000-a7757eb786bf7e3ad834 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 20V, Positive-QTOF | splash10-0zfr-0096000000-5c94c721117275f9900e | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 40V, Positive-QTOF | splash10-00mp-1592000000-c76c3d31b5b1be573731 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 10V, Negative-QTOF | splash10-0002-0005900000-64725de0ce689f591dd6 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 20V, Negative-QTOF | splash10-0gi1-1079100000-902e7f94588ce21152e6 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 40V, Negative-QTOF | splash10-0f8i-9065000000-a666caa78563c7dd062a | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 10V, Positive-QTOF | splash10-0udi-0002900000-d64b550422eb6f346c74 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 20V, Positive-QTOF | splash10-0zmi-0091000000-d9d6087fc9775370a1de | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 40V, Positive-QTOF | splash10-0pb9-4961000000-592d2646aa22737a0ecb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 10V, Negative-QTOF | splash10-0002-0000900000-c8698967a7d548475164 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 20V, Negative-QTOF | splash10-0002-9000200000-1db080bae05d677ddd47 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 40V, Negative-QTOF | splash10-0002-9000100000-7d3e3cd58a127b09b14f | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - Shin SY, Fauman EB, Petersen AK, Krumsiek J, Santos R, Huang J, Arnold M, Erte I, Forgetta V, Yang TP, Walter K, Menni C, Chen L, Vasquez L, Valdes AM, Hyde CL, Wang V, Ziemek D, Roberts P, Xi L, Grundberg E, Waldenberger M, Richards JB, Mohney RP, Milburn MV, John SL, Trimmer J, Theis FJ, Overington JP, Suhre K, Brosnan MJ, Gieger C, Kastenmuller G, Spector TD, Soranzo N: An atlas of genetic influences on human blood metabolites. Nat Genet. 2014 Jun;46(6):543-550. doi: 10.1038/ng.2982. Epub 2014 May 11. [PubMed:24816252 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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