Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:18:00 UTC |
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Update Date | 2022-03-07 02:49:16 UTC |
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HMDB ID | HMDB0002642 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ursodeoxycholic acid 3-sulfate |
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Description | Ursodeoxycholic acid 3-sulfate belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. Ursodeoxycholic acid 3-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)CC2C[C@H](CC[C@]12C)OS(O)(=O)=O InChI=1S/C24H40O7S/c1-14(4-7-21(26)27)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(31-32(28,29)30)12-15(23)13-20(22)25/h14-20,22,25H,4-13H2,1-3H3,(H,26,27)(H,28,29,30)/t14-,15?,16+,17-,18+,19+,20+,22+,23+,24-/m1/s1 |
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Synonyms | Value | Source |
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Ursodeoxycholate 3-sulfate | Generator | Ursodeoxycholate 3-sulphate | Generator | Ursodeoxycholic acid 3-sulfuric acid | Generator | Ursodeoxycholic acid 3-sulphuric acid | Generator | (4R)-4-[(1S,2S,5S,9S,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate | HMDB | (4R)-4-[(1S,2S,5S,9S,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate | HMDB | (4R)-4-[(1S,2S,5S,9S,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid | HMDB | (3a,5b,7b)-7-Hydroxy-3-(sulfooxy)-cholan-24-Oate | HMDB | (3a,5b,7b)-7-Hydroxy-3-(sulfooxy)-cholan-24-Oic acid | HMDB | Ursodeoxycholic acid 3-sulphate | HMDB |
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Chemical Formula | C24H40O7S |
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Average Molecular Weight | 472.635 |
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Monoisotopic Molecular Weight | 472.249474324 |
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IUPAC Name | (4R)-4-[(1S,2S,5S,9S,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid |
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Traditional Name | ursodeoxycholic acid 3-sulfate |
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CAS Registry Number | 68780-73-4 |
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SMILES | [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)CC2C[C@H](CC[C@]12C)OS(O)(=O)=O |
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InChI Identifier | InChI=1S/C24H40O7S/c1-14(4-7-21(26)27)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(31-32(28,29)30)12-15(23)13-20(22)25/h14-20,22,25H,4-13H2,1-3H3,(H,26,27)(H,28,29,30)/t14-,15?,16+,17-,18+,19+,20+,22+,23+,24-/m1/s1 |
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InChI Key | WHMOBEGYTDWMIG-ROKSHQGPSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. |
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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 | Bile acids, alcohols and derivatives |
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Direct Parent | Monohydroxy bile acids, alcohols and derivatives |
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Alternative Parents | |
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Substituents | - Monohydroxy bile acid, alcohol, or derivatives
- Sulfated steroid skeleton
- Hydroxysteroid
- 7-hydroxysteroid
- 7-alpha-hydroxysteroid
- Sulfuric acid ester
- Alkyl sulfate
- Sulfate-ester
- Sulfuric acid monoester
- Cyclic alcohol
- Organic sulfuric acid or derivatives
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- 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 | 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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Ursodeoxycholic acid 3-sulfate,1TMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3796.4 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,1TMS,isomer #2 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3720.1 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,1TMS,isomer #3 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3816.8 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,2TMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3686.4 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,2TMS,isomer #2 | C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3789.7 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,2TMS,isomer #3 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3726.8 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,3TMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3675.9 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,3TMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 4096.7 | Standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,3TMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 4435.8 | Standard polar | 33892256 | Ursodeoxycholic acid 3-sulfate,1TBDMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C | 4060.4 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,1TBDMS,isomer #2 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3937.8 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,1TBDMS,isomer #3 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 4006.3 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,2TBDMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C | 4170.8 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,2TBDMS,isomer #2 | C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 4244.1 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,2TBDMS,isomer #3 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 4119.8 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,3TBDMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 4298.7 | Semi standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,3TBDMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 4937.3 | Standard non polar | 33892256 | Ursodeoxycholic acid 3-sulfate,3TBDMS,isomer #1 | C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)CC4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 4567.1 | 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 - Ursodeoxycholic acid 3-sulfate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0536-0667900000-f5e817c86afceff3bc92 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ursodeoxycholic acid 3-sulfate GC-MS (2 TMS) - 70eV, Positive | splash10-0udi-3221659000-590f9fc72ad84350b04e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ursodeoxycholic acid 3-sulfate 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 - Ursodeoxycholic acid 3-sulfate 10V, Positive-QTOF | splash10-0a4i-0002900000-abbbbfd5950c6cf2e226 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 20V, Positive-QTOF | splash10-056r-0009200000-087c5d2f48d7160b5dbc | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 40V, Positive-QTOF | splash10-0a4j-1229200000-7f1303ebc6e2d806539e | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 10V, Negative-QTOF | splash10-00di-0001900000-bff4b187cc87bfca1cd0 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 20V, Negative-QTOF | splash10-00dl-2009400000-eab51a83a4551fd439fd | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 40V, Negative-QTOF | splash10-0a5a-9007100000-7432e93f953dc907a065 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 10V, Positive-QTOF | splash10-00di-0002900000-06cd8122555b78f76406 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 20V, Positive-QTOF | splash10-0a4i-1019200000-1a2383b307a87525bad2 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 40V, Positive-QTOF | splash10-004i-1589000000-3a790fd1e8a788615b2e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 10V, Negative-QTOF | splash10-00di-0000900000-29034312137a9db3fb88 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 20V, Negative-QTOF | splash10-00di-1000900000-ade2350b3441a8a2d002 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ursodeoxycholic acid 3-sulfate 40V, Negative-QTOF | splash10-0002-9006400000-0a3dcf516ded28a9a1aa | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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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 | Detected and Quantified | 0.19 (0.1-0.7) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 38.0 +/- 19.0 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 1.43 +/- 3.38 nmol/g wet feces | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | 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 | FDB023036 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 13628379 |
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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 | 6728 |
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PubChem Compound | 21252318 |
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PDB ID | Not Available |
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ChEBI ID | 89499 |
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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 | Bandiera, Tiziano; Albini, Franca Marinone; Albini, Enrico. A convenient procedure for the synthesis of ursodeoxycholic acid sulfated derivatives. Synthetic Communications (1987), 17(9), 1111-17. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Goto J, Kato H, Saruta Y, Nambara T: Studies on steroids. CLXX. Separation and determination of bile acid 3-sulfates in human bile by high-performance liquid chromatography. J Chromatogr. 1981 Nov 13;226(1):13-24. [PubMed:7320139 ]
- Goto T, Myint KT, Sato K, Wada O, Kakiyama G, Iida T, Hishinuma T, Mano N, Goto J: LC/ESI-tandem mass spectrometric determination of bile acid 3-sulfates in human urine 3beta-Sulfooxy-12alpha-hydroxy-5beta-cholanoic acid is an abundant nonamidated sulfate. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):69-77. Epub 2006 Sep 1. [PubMed:16949895 ]
- Pacini N, Albini E, Ferrari A, Zanchi R, Marca G, Bandiera T: Transformation of sulfated bile acids by human intestinal microflora. Arzneimittelforschung. 1987 Aug;37(8):983-7. [PubMed:3675701 ]
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