Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-23 20:41:17 UTC |
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Update Date | 2021-09-23 20:41:17 UTC |
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HMDB ID | HMDB0302788 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | beta-Cedrene |
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Description | α-Cedrene also known as Cedrene, belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiterpenoids with a structure based on the cedrane or the isocedrane skeleton. Isocedrane is a rearranged cedrane arising from the migration of a methyl group from the position 6 to the position 4. Sesquiterpenoides are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. α-Cedrene is a tricyclic molecule based on a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. α-Cedrene is a naturally occurring tricyclic sesquiterpene found in the essential oil of cedar. There are two known cedrene isomers, namely α- and β-cedrene, which differ in the position of a double bond. |
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Structure | [H][C@@]12CC[C@@H](C)[C@]11C[C@@H](C(=C)CC1)C2(C)C InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h11-13H,1,5-9H2,2-4H3/t11-,12+,13+,15+/m1/s1 |
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Synonyms | Value | Source |
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b-Cedrene | Generator | Β-cedrene | Generator | Cedrone | MeSH | alpha-Cedrene | MeSH | Cedrene | MeSH |
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Chemical Formula | C15H24 |
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Average Molecular Weight | 204.3511 |
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Monoisotopic Molecular Weight | 204.187800768 |
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IUPAC Name | (1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0^{1,5}]undecane |
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Traditional Name | (1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0^{1,5}]undecane |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]12CC[C@@H](C)[C@]11C[C@@H](C(=C)CC1)C2(C)C |
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InChI Identifier | InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h11-13H,1,5-9H2,2-4H3/t11-,12+,13+,15+/m1/s1 |
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InChI Key | DYLPEFGBWGEFBB-OSFYFWSMSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. |
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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 | Cedrane and isocedrane sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Cedrane sesquiterpenoid
- Branched unsaturated hydrocarbon
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- 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 | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 10V, Positive-QTOF | splash10-0a4i-0190000000-160394d3d26f706157c6 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 20V, Positive-QTOF | splash10-0a4i-1790000000-e6f0484b6a92d5df01d2 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 40V, Positive-QTOF | splash10-0ky0-8900000000-f8464b212174dc736609 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 10V, Negative-QTOF | splash10-0udi-0090000000-139f56b646b5d2bd9331 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 20V, Negative-QTOF | splash10-0udi-0090000000-93640a2ea4701a286b3c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 40V, Negative-QTOF | splash10-000i-1910000000-97e69de92b5437f20d9f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 10V, Positive-QTOF | splash10-0a4i-0090000000-bfe3306c5c32cdb9f028 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 20V, Positive-QTOF | splash10-0w29-0980000000-0d54002ce2f150d93292 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 40V, Positive-QTOF | splash10-0002-3910000000-86af0a94fe4a8ae930dd | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 10V, Negative-QTOF | splash10-0udi-0090000000-7ccf03fa1149a1e9f55f | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 20V, Negative-QTOF | splash10-0udi-0090000000-7ccf03fa1149a1e9f55f | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Cedrene 40V, Negative-QTOF | splash10-0udi-0090000000-fc9228a641e3e70e9650 | 2021-10-21 | Wishart Lab | View Spectrum |
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General References | - Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
- Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
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