Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 23:28:32 UTC |
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Update Date | 2022-03-07 02:55:40 UTC |
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HMDB ID | HMDB0038195 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Xanthorrhizol |
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Description | Xanthorrhizol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Xanthorrhizol. |
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Structure | CC(CCC=C(C)C)C1=CC(O)=C(C)C=C1 InChI=1S/C15H22O/c1-11(2)6-5-7-12(3)14-9-8-13(4)15(16)10-14/h6,8-10,12,16H,5,7H2,1-4H3 |
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Synonyms | Value | Source |
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(-)-5-(1,5-Dimethyl-4-hexenyl)-2-methylphenol | HMDB | (R)-(-)-Xanthorrhizol | HMDB | (R)-5-(1,5-Dimethyl-4-hexenyl)-O-cresol | HMDB | (R)-5-(1-5-Dimethyl-4-hexenyl)-2-methylphenol | HMDB | 5-(1,5-Dimethyl-4-hexenyl)-(-)-O-cresol | HMDB | 5-(1,5-Dimethyl-4-hexenyl)-2-methyl-(-)-phenol | HMDB | 5-(1,5-Dimethyl-4-hexenyl)-2-methylphenol | HMDB | 5-(1,5-Dimethyl-4-hexenyl)-2-methylphenol, 9ci | HMDB | 5-[(1R)-1,5-Dimethyl-4-hexenyl]-2-methyl-phenol | HMDB |
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Chemical Formula | C15H22O |
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Average Molecular Weight | 218.3346 |
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Monoisotopic Molecular Weight | 218.167065326 |
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IUPAC Name | 2-methyl-5-(6-methylhept-5-en-2-yl)phenol |
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Traditional Name | 2-methyl-5-(6-methylhept-5-en-2-yl)phenol |
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CAS Registry Number | 30199-26-9 |
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SMILES | CC(CCC=C(C)C)C1=CC(O)=C(C)C=C1 |
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InChI Identifier | InChI=1S/C15H22O/c1-11(2)6-5-7-12(3)14-9-8-13(4)15(16)10-14/h6,8-10,12,16H,5,7H2,1-4H3 |
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InChI Key | FKWGCEDRLNNZOZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive 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 | Sesquiterpenoids |
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Direct Parent | Sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Bisabolane sesquiterpenoid
- Sesquiterpenoid
- P-cymene
- O-cresol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Toluene
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | Not Available |
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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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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Xanthorrhizol GC-MS (Non-derivatized) - 70eV, Positive | splash10-000i-5910000000-bbbc808402d4ed1b9d87 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Xanthorrhizol GC-MS (1 TMS) - 70eV, Positive | splash10-05di-9380000000-5efc594d791232cfba9e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Xanthorrhizol 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 - Xanthorrhizol 10V, Positive-QTOF | splash10-014i-1490000000-7b7917bbd2d076a6a1bd | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Positive-QTOF | splash10-014i-3930000000-f36e65d14851d985f07c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Positive-QTOF | splash10-0ldi-9500000000-5dae3bd921c5b051d077 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 10V, Negative-QTOF | splash10-014i-0090000000-e9ece6fa864d7f85bd6e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Negative-QTOF | splash10-014i-0190000000-825f4354c46942faba2f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Negative-QTOF | splash10-0zgr-2920000000-ed263b9c3352ae00c36f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 10V, Negative-QTOF | splash10-014i-0090000000-868e2fb00a2cfbf6c529 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Negative-QTOF | splash10-014i-0690000000-832a55e37cc53c279022 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Negative-QTOF | splash10-001i-0900000000-9c4703d7c228cc18545c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 10V, Positive-QTOF | splash10-0a4i-9500000000-6361694e7914d5c8167b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Positive-QTOF | splash10-05ox-9200000000-ded2bd26eb1ced7c2c22 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Positive-QTOF | splash10-052f-9600000000-92500c706afd0d6d2d87 | 2021-09-22 | Wishart Lab | View Spectrum |
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General References | - Mustaffa F, Indurkar J, Ismail S, Shah M, Mansor SM: An antimicrobial compound isolated from Cinnamomum iners leaves with activity against methicillin-resistant Staphylococcus aureus. Molecules. 2011 Apr 8;16(4):3037-47. doi: 10.3390/molecules16043037. [PubMed:21478819 ]
- Handayani T, Sakinah S, Nallappan M, Pihie AH: Regulation of p53-, Bcl-2- and caspase-dependent signaling pathway in xanthorrhizol-induced apoptosis of HepG2 hepatoma cells. Anticancer Res. 2007 Mar-Apr;27(2):965-71. [PubMed:17465228 ]
- Lee LY, Shim JS, Rukayadi Y, Hwang JK: Antibacterial activity of xanthorrhizol isolated from Curcuma xanthorrhiza Roxb. against foodborne pathogens. J Food Prot. 2008 Sep;71(9):1926-30. [PubMed:18810881 ]
- 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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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