Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2009-04-06 16:20:19 UTC |
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Update Date | 2022-03-07 02:51:21 UTC |
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HMDB ID | HMDB0012166 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol |
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Description | 4alpha-carboxy-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 NAD(P)-dependent steroid dehydrogenase (H105E3) and it can be generated from the enzymatic carboxylation of 5alpha-cholesta-8-en-3-one. It is also a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic oxidation of 4alpha-formyl-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@H](C1CC3)C(O)=O InChI=1S/C28H46O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h17-18,20-21,23-25,29H,6-16H2,1-5H3,(H,30,31)/t18?,20?,21?,23?,24-,25-,27+,28+/m0/s1 |
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Synonyms | Value | Source |
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4a-Carboxy-5a-cholesta-8-en-3b-ol | Generator | 4Α-carboxy-5α-cholesta-8-en-3β-ol | Generator | 4a-Carboxy-5a-cholesta-8-en-3beta-ol | HMDB | 4alpha-Carboxy-5alpha-cholesta-8-en-3b-ol | HMDB | (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-carboxylate | Generator |
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Chemical Formula | C28H46O3 |
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Average Molecular Weight | 430.663 |
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Monoisotopic Molecular Weight | 430.344695338 |
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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-carboxylic acid |
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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-carboxylic acid |
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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](C1CC3)C(O)=O |
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InChI Identifier | InChI=1S/C28H46O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h17-18,20-21,23-25,29H,6-16H2,1-5H3,(H,30,31)/t18?,20?,21?,23?,24-,25-,27+,28+/m0/s1 |
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InChI Key | RODBXVVNKJCWQR-KLZNZPMLSA-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
- Steroid acid
- 4-carboxy steroid
- 3-hydroxysteroid
- 15-hydroxysteroid
- Hydroxysteroid
- 3-beta-hydroxysteroid
- Beta-hydroxy acid
- Hydroxy acid
- Cyclic alcohol
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- 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 | |
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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 | | Show more...
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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-Carboxy-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)O)C1CC3 | 3520.0 | Semi standard non polar | 33892256 | 4alpha-Carboxy-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@@H](C(=O)O[Si](C)(C)C)C1CC3 | 3462.2 | Semi standard non polar | 33892256 | 4alpha-Carboxy-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@@H](C(=O)O[Si](C)(C)C)C1CC3 | 3461.6 | Semi standard non polar | 33892256 | 4alpha-Carboxy-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)O)C1CC3 | 3749.5 | Semi standard non polar | 33892256 | 4alpha-Carboxy-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@@H](C(=O)O[Si](C)(C)C(C)(C)C)C1CC3 | 3721.6 | Semi standard non polar | 33892256 | 4alpha-Carboxy-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@@H](C(=O)O[Si](C)(C)C(C)(C)C)C1CC3 | 3940.3 | Semi standard non polar | 33892256 |
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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-Carboxy-5alpha-cholesta-8-en-3beta-ol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0j4i-1009500000-d0500fdc254a799c072d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol GC-MS (2 TMS) - 70eV, Positive | splash10-08fr-3101390000-46cdde9e4e8648d63301 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4alpha-Carboxy-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-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOF | splash10-03e9-0004900000-3407ec9be563d9b7ca26 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOF | splash10-03xs-3019400000-d27da2a126830b00ff9d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOF | splash10-066u-6239200000-f3726ed20f097b0424ea | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOF | splash10-004i-0004900000-77d8d1520aaeaa4fd388 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOF | splash10-00n0-0009500000-1fbb5a29da673f0e742a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOF | splash10-014i-1009100000-5ad9f534d16a48a405c1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Negative-QTOF | splash10-004r-0008900000-250dce703c733254dfb5 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Negative-QTOF | splash10-000i-0009000000-eddf0611bb25b50405f8 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Negative-QTOF | splash10-014r-0009000000-8175a5e0027417e0b0ce | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 10V, Positive-QTOF | splash10-001i-0005900000-f3b4f582c48804094069 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 20V, Positive-QTOF | splash10-06a3-6259400000-4c8ff808d75df1d51209 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 40V, Positive-QTOF | splash10-0aov-9213000000-7b6183a193d666f727d2 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Inflammatory bowel disease | | details |
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Associated Disorders and Diseases |
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Disease References | Inflammatory bowel disease |
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- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
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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 | FDB028820 |
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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 | 25200718 |
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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 ]
- 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 ]
- 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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