Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2008-08-14 17:57:44 UTC |
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Update Date | 2022-03-07 02:49:34 UTC |
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HMDB ID | HMDB0006887 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 7a,12a-Dihydroxy-5b-cholestan-3-one |
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Description | 7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one is an intermediate in bile acid biosynthesis. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). |
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Structure | [H][C@]12CCC(C(C)CCCC(C)C)[C@@]1(C)C([H])(O)C[C@@]1([H])C2[C@H](O)CC2CC(=O)CC[C@]12C InChI=1S/C27H46O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-18,20-25,29-30H,6-15H2,1-5H3/t17?,18?,20?,21-,22+,23-,24-,25?,26+,27-/m1/s1 |
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Synonyms | Value | Source |
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5b-Cholestane-7a,12a-diol-3-one | HMDB | 5beta-Cholestane-7alpha,12alpha-diol-3-one | HMDB | 7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one | HMDB |
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Chemical Formula | C27H46O3 |
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Average Molecular Weight | 418.6523 |
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Monoisotopic Molecular Weight | 418.344695338 |
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IUPAC Name | (1S,2S,9R,11R,15R)-9,16-dihydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one |
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Traditional Name | (1S,2S,9R,11R,15R)-9,16-dihydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one |
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CAS Registry Number | Not Available |
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SMILES | [H][C@]12CCC(C(C)CCCC(C)C)[C@@]1(C)C([H])(O)C[C@@]1([H])C2[C@H](O)CC2CC(=O)CC[C@]12C |
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InChI Identifier | InChI=1S/C27H46O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-18,20-25,29-30H,6-15H2,1-5H3/t17?,18?,20?,21-,22+,23-,24-,25?,26+,27-/m1/s1 |
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InChI Key | HHVQPBXBALLUDF-JEUKKHAPSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerolipids |
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Sub Class | Diradylglycerols |
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Direct Parent | 1,2-diacylglycerols |
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Alternative Parents | |
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Substituents | - 1,2-acyl-sn-glycerol
- Fatty acid ester
- Fatty acyl
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | |
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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 | |
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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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7a,12a-Dihydroxy-5b-cholestan-3-one,1TMS,isomer #1 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O | 3464.9 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,1TMS,isomer #2 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O[Si](C)(C)C | 3473.9 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,1TMS,isomer #3 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@H]3O | 3422.3 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,1TMS,isomer #4 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@H]3O | 3423.9 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,2TMS,isomer #1 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O[Si](C)(C)C | 3388.3 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,2TMS,isomer #2 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@H]3O | 3386.4 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,2TMS,isomer #3 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@H]3O | 3372.8 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,2TMS,isomer #4 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@H]3O[Si](C)(C)C | 3390.1 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,2TMS,isomer #5 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C | 3387.7 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TMS,isomer #1 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@H]3O[Si](C)(C)C | 3315.7 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TMS,isomer #1 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@H]3O[Si](C)(C)C | 3239.5 | Standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TMS,isomer #1 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@H]3O[Si](C)(C)C | 3360.2 | Standard polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TMS,isomer #2 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C | 3308.6 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TMS,isomer #2 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C | 3231.1 | Standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TMS,isomer #2 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C | 3361.0 | Standard polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,1TBDMS,isomer #1 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O | 3677.0 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,1TBDMS,isomer #2 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C | 3693.1 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,1TBDMS,isomer #3 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O | 3670.7 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,1TBDMS,isomer #4 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O | 3668.9 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,2TBDMS,isomer #1 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C | 3795.8 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,2TBDMS,isomer #2 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O | 3858.5 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,2TBDMS,isomer #3 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O | 3833.5 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,2TBDMS,isomer #4 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O[Si](C)(C)C(C)(C)C | 3862.6 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,2TBDMS,isomer #5 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C | 3855.1 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TBDMS,isomer #1 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O[Si](C)(C)C(C)(C)C | 3978.2 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TBDMS,isomer #1 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O[Si](C)(C)C(C)(C)C | 3790.7 | Standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TBDMS,isomer #1 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O[Si](C)(C)C(C)(C)C | 3600.6 | Standard polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TBDMS,isomer #2 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C | 3962.6 | Semi standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TBDMS,isomer #2 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C | 3713.8 | Standard non polar | 33892256 | 7a,12a-Dihydroxy-5b-cholestan-3-one,3TBDMS,isomer #2 | CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C | 3600.3 | 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 - 7a,12a-Dihydroxy-5b-cholestan-3-one GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fk9-0549200000-dceadac2ca32e85a9fdd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one GC-MS (2 TMS) - 70eV, Positive | splash10-0002-5542590000-b45c345b88b2b3b46f03 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 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 - 7a,12a-Dihydroxy-5b-cholestan-3-one 10V, Positive-QTOF | splash10-0uxr-0005900000-9f54eab9eecc22e26713 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 20V, Positive-QTOF | splash10-0ul3-3209300000-09494edc1c2008eab65e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 40V, Positive-QTOF | splash10-0ab9-5209000000-ede875adbb4dc1186f60 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 10V, Negative-QTOF | splash10-014i-0004900000-bf213248ab899a2b7bee | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 20V, Negative-QTOF | splash10-014j-0008900000-2d5e0f8ee4e8dbf0e7b5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 40V, Negative-QTOF | splash10-0f79-2109200000-af8562b835f573a2f41e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 10V, Positive-QTOF | splash10-014i-1002900000-25d4c3065d4dd0943636 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 20V, Positive-QTOF | splash10-0kui-9246500000-f173aa82bf42c825c978 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 40V, Positive-QTOF | splash10-0a4i-9510000000-81b09eb12b57d9f34005 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 10V, Negative-QTOF | splash10-014i-0000900000-f2cb6399034352e924c8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 20V, Negative-QTOF | splash10-014i-0001900000-fbf80cd6881af08fa3a6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 40V, Negative-QTOF | splash10-014i-0029500000-3c9e6f7da209a7490e5f | 2021-09-22 | Wishart Lab | View Spectrum |
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