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 14:17:58 UTC |
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Update Date | 2022-03-07 02:49:16 UTC |
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HMDB ID | HMDB0002586 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Chenodeoxycholic acid 3-sulfate |
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Description | Chenodeoxycholic acid 3-sulfate, also known as 3-sulfochenodeoxycholate or CDCS, 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. Chenodeoxycholic acid 3-sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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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)C[C@]2([H])C[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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Chenodeoxycholate 3-sulfate | Generator | Chenodeoxycholate 3-sulphate | Generator | Chenodeoxycholic acid 3-sulfuric acid | Generator | Chenodeoxycholic acid 3-sulphuric acid | Generator | 3-Sulfochenodeoxycholate | HMDB | 3-Sulfochenodeoxycholic acid | HMDB | Chenodeoxycholic acid 3-sulphate | HMDB | Chenodeoxycholic acid 3a-sulfate | HMDB | Chenodeoxycholic acid 3a-sulphate | HMDB | CDCS | HMDB | Chenodeoxycholate sulfate conjugate | HMDB | Chenodeoxycholic acid sulfate conjugate | 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,5R,7R,9R,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 | (4R)-4-[(1S,2S,5R,7R,9R,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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CAS Registry Number | 59132-32-0 |
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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)C[C@]2([H])C[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-BSWAIDMHSA-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
- 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 | |
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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 | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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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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Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O | 3789.0 | Semi standard non polar | 33892256 | Chenodeoxycholic acid 3-sulfate,1TMS,isomer #2 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O[Si](C)(C)C | 3697.0 | Semi standard non polar | 33892256 | Chenodeoxycholic acid 3-sulfate,1TMS,isomer #3 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O | 3809.7 | Semi standard non polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O[Si](C)(C)C | 3670.3 | Semi standard non polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O | 3788.0 | Semi standard non polar | 33892256 | Chenodeoxycholic acid 3-sulfate,2TMS,isomer #3 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C | 3714.5 | Semi standard non polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C | 3673.8 | Semi standard non polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C | 4100.1 | Standard non polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C | 4462.3 | Standard polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O | 4062.5 | Semi standard non polar | 33892256 | Chenodeoxycholic acid 3-sulfate,1TBDMS,isomer #2 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C | 3924.9 | Semi standard non polar | 33892256 | Chenodeoxycholic acid 3-sulfate,1TBDMS,isomer #3 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O | 4005.8 | Semi standard non polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C | 4168.6 | Semi standard non polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O | 4246.8 | Semi standard non polar | 33892256 | Chenodeoxycholic acid 3-sulfate,2TBDMS,isomer #3 | C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C | 4113.0 | Semi standard non polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C | 4302.0 | Semi standard non polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C | 4941.4 | Standard non polar | 33892256 | Chenodeoxycholic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C | 4592.9 | Standard polar | 33892256 |
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