Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 17:34:13 UTC |
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Update Date | 2022-03-07 02:52:24 UTC |
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HMDB ID | HMDB0030021 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Fucosterol |
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Description | Fucosterol, also known as fucosterin, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Fucosterol is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | C\C=C(\C(C)C)CC[C@@H](C)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+/t20-,23+,24?,25?,26?,27?,28+,29-/m1/s1 |
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Synonyms | Value | Source |
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(24E)-Ethylidenecholesterol | HMDB | (3b,24E)-Stigmasta-5,24(28)-dien-3-ol | HMDB | (e)-24-Ethylidenecholesterol | HMDB | (e)-Stigmasta-5,24(28)-dien-3b-ol | HMDB | 24(e)-Ethylidenecholest-5-en-3beta -ol | HMDB | Fucosterin | HMDB | Stigmasta-5,24(28)-dien-3beta (e)--ol | HMDB | trans-24-Ethylidenecholesterol | HMDB | trans-D5-Avenosterol | HMDB | (24E)-24-N-Propylidenecholesterol | MeSH | delta(5)-Avenasterol | MeSH | Fucosterol | MeSH | Stigmasta-5,24-dien-3 beta-ol | MeSH | 24-Isoethylidenecholest-5-en-3 beta-ol,delta(5)-avenasterol | MeSH | 24Z-Ethylidenecholest-5-en-3b-ol | MeSH | 28-Isofucosterol | MeSH | Fucosterol, (3beta)-isomer | MeSH | Fucosterol, 28-(14)C-labeled CPD, (e)-isomer | MeSH |
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Chemical Formula | C29H48O |
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Average Molecular Weight | 412.6908 |
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Monoisotopic Molecular Weight | 412.370516158 |
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IUPAC Name | (2R,5S,15R)-2,15-dimethyl-14-[(2R,5E)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol |
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Traditional Name | (2R,5S,15R)-14-[(2R,5E)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol |
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CAS Registry Number | 17605-67-3 |
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SMILES | C\C=C(\C(C)C)CC[C@@H](C)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C |
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InChI Identifier | InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+/t20-,23+,24?,25?,26?,27?,28+,29-/m1/s1 |
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InChI Key | OSELKOCHBMDKEJ-ZMRGBFEOSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. |
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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 | Stigmastanes and derivatives |
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Direct Parent | Stigmastanes and derivatives |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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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 | |
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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 | 124 °C | 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 IndicesUnderivatizedDerivatized |
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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 - Fucosterol GC-MS (Non-derivatized) - 70eV, Positive | splash10-001j-0109000000-a1e9aa5ecd141028d574 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Fucosterol GC-MS (1 TMS) - 70eV, Positive | splash10-06di-2104900000-fd4678ce9164cc207101 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Fucosterol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Fucosterol 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 - Fucosterol 10V, Positive-QTOF | splash10-01ot-1019500000-bcaac8318b52fbef2725 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 20V, Positive-QTOF | splash10-0002-6259100000-c5a8fd880d63c55bcacf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 40V, Positive-QTOF | splash10-0002-7094000000-d9a6cedb0a89fad97057 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 10V, Negative-QTOF | splash10-03di-0002900000-82a40a2a370fc124e6ef | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 20V, Negative-QTOF | splash10-03di-0005900000-96d823e5c0a704f96e3d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 40V, Negative-QTOF | splash10-0002-2009000000-6ab638e744dcb194bcf2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 10V, Positive-QTOF | splash10-000i-0009000000-3435c916b009674ed73f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 20V, Positive-QTOF | splash10-0mji-9034100000-a276943f018a4b6c0c67 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 40V, Positive-QTOF | splash10-0a4i-9720000000-ad3d3c3e6638fa490e55 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 10V, Negative-QTOF | splash10-03di-0000900000-363450e12a0ea926276e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 20V, Negative-QTOF | splash10-03di-0002900000-091003fd0596352205d1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fucosterol 40V, Negative-QTOF | splash10-0a4i-0009700000-65d2076e7d57b208a3b0 | 2021-09-24 | Wishart Lab | View Spectrum |
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Disease References | Colorectal cancer |
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- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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