Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-10-30 13:54:46 UTC |
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Update Date | 2022-03-07 02:51:03 UTC |
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HMDB ID | HMDB0011181 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Brassicasterol |
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Description | Brassicasterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, brassicasterol is considered to be a sterol lipid molecule. Brassicasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Brassicasterol is a potential CSF biomarker for Alzheimer’s disease (PMID: 21585343 ). |
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Structure | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1 |
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Synonyms | Value | Source |
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(22E,24R)-24-Methylcholesta-5,22-dien-3beta-ol | ChEBI | (3beta,22E)-Ergosta-5,22-dien-3-ol | ChEBI | 24(R)-Methylcholesta-5,22E-dien-3beta-ol | ChEBI | 24-Methyl cholest-5,22-dien-3beta-ol | ChEBI | Brassicasterin | ChEBI | Ergosta-5,22(e)-dien-3beta-ol | ChEBI | Ergosta-5,22E-dien-3beta-ol | ChEBI | (22E,24R)-24-Methylcholesta-5,22-dien-3b-ol | Generator | (22E,24R)-24-Methylcholesta-5,22-dien-3β-ol | Generator | (3b,22E)-Ergosta-5,22-dien-3-ol | Generator | (3Β,22E)-ergosta-5,22-dien-3-ol | Generator | 24(R)-Methylcholesta-5,22E-dien-3b-ol | Generator | 24(R)-Methylcholesta-5,22E-dien-3β-ol | Generator | 24-Methyl cholest-5,22-dien-3b-ol | Generator | 24-Methyl cholest-5,22-dien-3β-ol | Generator | Ergosta-5,22(e)-dien-3b-ol | Generator | Ergosta-5,22(e)-dien-3β-ol | Generator | Ergosta-5,22E-dien-3b-ol | Generator | Ergosta-5,22E-dien-3β-ol | Generator | 24 beta-Methylcholesta-5,22-dien-3 beta-ol | HMDB | Ergosta-5,22-dien-3 beta-ol | HMDB | trans-22-Dehydrocampestrol | HMDB | Epibrassicasterol | HMDB | (22E,24R)-Ergosta-5,22-dien-3beta-ol | HMDB | (22E,24R)-Ergosta-5,22-dien-3β-ol | HMDB | 24-Methylcholesta-5,22-dien-3beta-ol | HMDB | 24-Methylcholesta-5,22-dien-3β-ol | HMDB | Ergosta-5,22-dien-3beta-ol | HMDB | Ergosta-5,22-dien-3β-ol | HMDB | delta5,22-Ergostadien-3beta-ol | HMDB | delta5,22-Ergostadienol | HMDB | Δ5,22-ergostadien-3β-ol | HMDB | Δ5,22-ergostadienol | HMDB | Brassicasterol | HMDB |
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Chemical Formula | C28H46O |
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Average Molecular Weight | 398.675 |
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Monoisotopic Molecular Weight | 398.354866101 |
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IUPAC Name | (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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Traditional Name | (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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CAS Registry Number | 474-67-9 |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C |
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InChI Identifier | InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1 |
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InChI Key | OILXMJHPFNGGTO-ZAUYPBDWSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. |
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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 | Ergostane steroids |
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Direct Parent | Ergosterols and derivatives |
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Alternative Parents | |
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Substituents | - Ergosterol-skeleton
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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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 | |
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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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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 ]
- Vanmierlo T, Popp J, Kolsch H, Friedrichs S, Jessen F, Stoffel-Wagner B, Bertsch T, Hartmann T, Maier W, von Bergmann K, Steinbusch H, Mulder M, Lutjohann D: The plant sterol brassicasterol as additional CSF biomarker in Alzheimer's disease. Acta Psychiatr Scand. 2011 Sep;124(3):184-92. doi: 10.1111/j.1600-0447.2011.01713.x. Epub 2011 May 17. [PubMed:21585343 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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