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 16:20:21 UTC |
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Update Date | 2022-03-07 02:51:21 UTC |
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HMDB ID | HMDB0012168 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol |
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Description | 4alpha-formyl-4beta-methyl-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 reduction of 4alpha-carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol or from the enzymatic oxidation of 4alpha-hydroxymethyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol. 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 | CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C=O)C1CC3 InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h18-20,22-23,25-26,31H,7-17H2,1-6H3/t20?,22?,23?,25?,26-,27+,28+,29-/m0/s1 |
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Synonyms | Value | Source |
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4a-Formyl-4b-methyl-5a-cholesta-8-en-3b-ol | Generator | 4Α-formyl-4β-methyl-5α-cholesta-8-en-3β-ol | Generator | 4a-Formyl-4beta-methyl-5a-cholesta-8-en-3beta-ol | HMDB | 4alpha-Formyl-4b-methyl-5alpha-cholesta-8-en-3b-ol | HMDB |
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Chemical Formula | C29H48O2 |
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Average Molecular Weight | 428.6902 |
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Monoisotopic Molecular Weight | 428.36543078 |
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IUPAC Name | (2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-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-2,6,15-trimethyl-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@@](C)(C=O)C1CC3 |
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InChI Identifier | InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h18-20,22-23,25-26,31H,7-17H2,1-6H3/t20?,22?,23?,25?,26-,27+,28+,29-/m0/s1 |
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InChI Key | WWTBBRMTEFBUND-AEWFMJFUSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Triterpenoids |
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Direct Parent | Triterpenoids |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Cholesterol-skeleton
- Cholestane-skeleton
- 3-hydroxysteroid
- 3-beta-hydroxysteroid
- Hydroxysteroid
- Steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- 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 | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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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-4beta-methyl-5alpha-cholesta-8-en-3beta-ol GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-2009400000-89039e9511b6d3a7dc65 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol GC-MS (1 TMS) - 70eV, Positive | splash10-0079-3002900000-38183aef23dc00c1e1f2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4alpha-Formyl-4beta-methyl-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-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOF | splash10-03fr-0002900000-d0724f8fcbdb51753986 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOF | splash10-08i9-7249800000-e5eaa216e135a4d8b3aa | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOF | splash10-0bti-5239100000-df2238454d4ce8f8c967 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOF | splash10-004i-0001900000-732e1ae6358556060196 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOF | splash10-004i-0002900000-e3b1b515f6458430a361 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOF | splash10-01qa-2009200000-6b92dfdff4f01338b91c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOF | splash10-004i-0007900000-e4c2dc37b5a8ebe51271 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOF | splash10-01si-2239300000-5d48ad8c3710f24233c3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOF | splash10-0a4i-9313000000-ead4f36849986264183f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOF | splash10-004i-0000900000-08c8d00e3f1ae63a05c9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOF | splash10-004i-0003900000-9531151bea81fdc990e0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOF | splash10-004i-0008900000-3ced068e2b26d8944722 | 2021-09-22 | Wishart Lab | View Spectrum |
| Show more...
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB028822 |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 25201774 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
- 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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