Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-04-06 16:20:22 UTC |
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Update Date | 2022-03-07 02:51:21 UTC |
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HMDB ID | HMDB0012169 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol |
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Description | 4alpha-formyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic oxidation of 4alpha-hydroxymethyl-5alpha-cholesta-8-en-3beta-ol or from the enzymatic reduction of 4alpha-carboxy-5alpha-cholesta-8-en-3beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis II (via 24,25-dihydrolanosterol) may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway. |
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Structure | CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C=O)C1CC3 InChI=1S/C28H46O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h17-19,21-24,26,30H,6-16H2,1-5H3/t19?,21-,22?,23?,24?,26-,27+,28-/m0/s1 |
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Synonyms | Value | Source |
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4a-Formyl-5a-cholesta-8-en-3b-ol | Generator | 4Α-formyl-5α-cholesta-8-en-3β-ol | Generator | 4a-Formyl-5a-cholesta-8-en-3beta-ol | HMDB | 4alpha-Formyl-5alpha-cholesta-8-en-3b-ol | HMDB |
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Chemical Formula | C28H46O2 |
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Average Molecular Weight | 414.6636 |
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Monoisotopic Molecular Weight | 414.349780716 |
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IUPAC Name | (2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carbaldehyde |
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Traditional Name | (2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carbaldehyde |
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CAS Registry Number | Not Available |
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SMILES | CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C=O)C1CC3 |
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InChI Identifier | InChI=1S/C28H46O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h17-19,21-24,26,30H,6-16H2,1-5H3/t19?,21-,22?,23?,24?,26-,27+,28-/m0/s1 |
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InChI Key | MHYWFGFPMGLYBL-GYISYUOESA-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-skeleton
- 3-beta-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aldehyde
- Alcohol
- 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 | Not Available |
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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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4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol,1TMS,isomer #1 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C=O)C1CC3 | 3391.2 | Semi standard non polar | 33892256 | 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol,1TMS,isomer #2 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)C(=CO[Si](C)(C)C)C1CC3 | 3362.4 | Semi standard non polar | 33892256 | 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol,2TMS,isomer #1 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)C(=CO[Si](C)(C)C)C1CC3 | 3408.9 | Semi standard non polar | 33892256 | 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol,2TMS,isomer #1 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)C(=CO[Si](C)(C)C)C1CC3 | 3354.9 | Standard non polar | 33892256 | 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol,2TMS,isomer #1 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)C(=CO[Si](C)(C)C)C1CC3 | 3580.6 | Standard polar | 33892256 | 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol,1TBDMS,isomer #1 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C=O)C1CC3 | 3621.9 | Semi standard non polar | 33892256 | 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol,1TBDMS,isomer #2 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)C(=CO[Si](C)(C)C(C)(C)C)C1CC3 | 3600.9 | Semi standard non polar | 33892256 | 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol,2TBDMS,isomer #1 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)C1CC3 | 3863.5 | Semi standard non polar | 33892256 | 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol,2TBDMS,isomer #1 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)C1CC3 | 3847.5 | Standard non polar | 33892256 | 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol,2TBDMS,isomer #1 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)C1CC3 | 3789.2 | 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 - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol GC-MS (Non-derivatized) - 70eV, Positive | splash10-03ds-1009000000-6eb86c9a3034173c252f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol GC-MS (1 TMS) - 70eV, Positive | splash10-0229-3005900000-bfdfcd101abbb675ff08 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 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 - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOF | splash10-00kb-0009400000-7ec89c963d8bf4c4eeb3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOF | splash10-05ot-4129100000-fd56fb0aab18b84544ee | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOF | splash10-0ap3-5139000000-66a2587d60a6f3e846f8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOF | splash10-03di-0003900000-5d87f50095cc7fa132fa | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOF | splash10-03di-0008900000-d532696886b27a754330 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOF | splash10-014j-1009000000-51cd56647cb59faff1f2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOF | splash10-014j-0009400000-15a572c1bb186f6c7ce5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOF | splash10-00ke-2039100000-2d308d8de7753eb2c6f3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOF | splash10-05ai-9002000000-00c8a2f323bada0235db | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOF | splash10-03di-0002900000-44587844a2c318dc9941 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOF | splash10-03di-0003900000-e02c42c72cf77c8a7ada | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOF | splash10-014r-0009000000-2258a326fe4c50d286bd | 2021-09-24 | Wishart Lab | View Spectrum |
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