Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-23 05:26:12 UTC |
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Update Date | 2022-03-07 03:17:58 UTC |
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HMDB ID | HMDB0062664 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4beta,7alpha-dihydroxycholesterol |
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Description | 4beta,7alpha-dihydroxycholesterol, also known as (3b,4b,7a)-cholest-5-ene-3,4,7-triol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 4beta,7alpha-dihydroxycholesterol is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | [H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C=C4[C@@]([H])(O)[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C InChI=1S/C27H46O3/c1-16(2)7-6-8-17(3)18-9-10-19-24-20(11-13-26(18,19)4)27(5)14-12-22(28)25(30)21(27)15-23(24)29/h15-20,22-25,28-30H,6-14H2,1-5H3/t17-,18-,19+,20+,22+,23-,24+,25-,26-,27-/m1/s1 |
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Synonyms | Value | Source |
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(3beta,4beta,7alpha)-Cholest-5-ene-3,4,7-triol | ChEBI | (3b,4b,7a)-Cholest-5-ene-3,4,7-triol | Generator | (3Β,4β,7α)-cholest-5-ene-3,4,7-triol | Generator | 4b,7a-Dihydroxycholesterol | Generator | 4Β,7α-dihydroxycholesterol | Generator |
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Chemical Formula | C27H46O3 |
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Average Molecular Weight | 418.662 |
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Monoisotopic Molecular Weight | 418.344695341 |
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IUPAC Name | (1S,2R,5S,6R,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,6,9-triol |
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Traditional Name | (1S,2R,5S,6R,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,6,9-triol |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C=C4[C@@]([H])(O)[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C |
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InChI Identifier | InChI=1S/C27H46O3/c1-16(2)7-6-8-17(3)18-9-10-19-24-20(11-13-26(18,19)4)27(5)14-12-22(28)25(30)21(27)15-23(24)29/h15-20,22-25,28-30H,6-14H2,1-5H3/t17-,18-,19+,20+,22+,23-,24+,25-,26-,27-/m1/s1 |
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InChI Key | NEITZYUKMAAGFE-DNPWHXEXSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
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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 | Cholestane steroids |
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Direct Parent | Cholesterols and derivatives |
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Alternative Parents | |
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Substituents | - Cholesterol
- Cholesterol-skeleton
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- 4-hydroxysteroid
- Hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- 3-beta-hydroxysteroid
- 7-hydroxysteroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Polyol
- Alcohol
- Organooxygen compound
- Organic oxygen compound
- 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 | Not Available |
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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 | 0.0078 g/l | ALOGPS | LogP | 4.78 | ALOGPS |
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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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4beta,7alpha-dihydroxycholesterol,1TMS,isomer #1 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3319.0 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,1TMS,isomer #2 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4[C@@H](O[Si](C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3284.6 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,1TMS,isomer #3 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4[C@@H](O)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3306.2 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,2TMS,isomer #1 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4[C@@H](O[Si](C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3221.4 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,2TMS,isomer #2 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4[C@@H](O)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3231.7 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,2TMS,isomer #3 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3244.5 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,3TMS,isomer #1 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3249.7 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,1TBDMS,isomer #1 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3569.2 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,1TBDMS,isomer #2 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3520.2 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,1TBDMS,isomer #3 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3551.1 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,2TBDMS,isomer #1 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C | 3671.0 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,2TBDMS,isomer #2 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3700.2 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,2TBDMS,isomer #3 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3678.9 | Semi standard non polar | 33892256 | 4beta,7alpha-dihydroxycholesterol,3TBDMS,isomer #1 | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C | 3885.0 | Semi standard non 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 - 4beta,7alpha-dihydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udr-1219300000-c6702bd055855b58c66a | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4beta,7alpha-dihydroxycholesterol GC-MS (3 TMS) - 70eV, Positive | splash10-00xr-3000049000-c6d07b25ee50c4c8471b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4beta,7alpha-dihydroxycholesterol 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 - 4beta,7alpha-dihydroxycholesterol 10V, Positive-QTOF | splash10-0uxr-0003900000-3efb8b309edd6516d428 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 20V, Positive-QTOF | splash10-0ue9-3239500000-a1c2768e3553af207034 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 40V, Positive-QTOF | splash10-0a4l-6469100000-460ff5914e21c928921d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 10V, Negative-QTOF | splash10-014i-0002900000-a3adeb011e7e33ee26eb | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 20V, Negative-QTOF | splash10-014j-0006900000-98af95f1704166a20938 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 40V, Negative-QTOF | splash10-0f79-1009200000-030346b52708c8208904 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 10V, Positive-QTOF | splash10-014i-0002900000-17aa19f795e99a700611 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 20V, Positive-QTOF | splash10-014i-8049800000-ccee4fce06c24a6340ef | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 40V, Positive-QTOF | splash10-0abc-9641000000-f97cd847a9503fa4d01c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 10V, Negative-QTOF | splash10-014i-0000900000-f2cb6399034352e924c8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 20V, Negative-QTOF | splash10-014i-0000900000-f2cb6399034352e924c8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4beta,7alpha-dihydroxycholesterol 40V, Negative-QTOF | splash10-014i-0005900000-6a6034dda2e103d31d2f | 2021-09-24 | Wishart Lab | View Spectrum |
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