Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-04-06 16:20:25 UTC |
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Update Date | 2020-02-26 21:37:03 UTC |
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HMDB ID | HMDB0012172 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol |
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Description | 4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis. It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from 4-alpha-methylzymosterol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis 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 | |
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Synonyms | Value | Source |
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4a-Hydroxymethyl-5a-cholesta-8,24-dien-3b-ol | Generator | 4Α-hydroxymethyl-5α-cholesta-8,24-dien-3β-ol | Generator | 4 alpha-Hysroxymethyl-5 alpha-cholsta-8,24-dien-3 beta-ol | HMDB | 4-alpha-Hysroxymethyl-5-alpha-cholsta-8,24-dien-3-beta-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,6R,15R)-6-(hydroxymethyl)-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol |
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Traditional Name | (2S,5S,6R,15R)-6-(hydroxymethyl)-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol |
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CAS Registry Number | Not Available |
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SMILES | CC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](CO)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/h7,19,21-24,26,29-30H,6,8-17H2,1-5H3/t19?,21-,22?,23?,24?,26-,27+,28-/m0/s1 |
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InChI Key | ORZKEIGPXNMCHC-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
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- 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 | Health effect: |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01pa-1009000000-26a6475677afe7b86ff0 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0006-3101390000-9a7be192c5b850bae998 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kb-0009200000-6a505952adf6b44c3471 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00os-2019000000-bfa43bfa929440dc0886 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-07br-3229000000-f36e1263e8ba538a453e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0005900000-10de80058b799a204f93 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03yj-0009300000-6ac3a41026db556615bf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-0009000000-3023571b31cb46c00627 | Spectrum |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
- Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..
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