| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:39:20 UTC |
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| Updated at | 2020-12-07 19:07:27 UTC |
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| CannabisDB ID | CDB000482 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | (+)-calarene |
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| Description | (+)-Calarene or Calarene belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Aristolanes arise from the C6, C11 cyclization of the bicyclic eremophilane skeleton. Sesquiterpenoids 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. It was identified in the essential oil of leaves of Rhododendron aureum (rosebay) (10.4% - 66.4% relative to total oil constituents) (DOI: 10.2298/JSC1002209O), the essential oil from Valeriana jatamansi Jones (Indian valerian or Tagar) (DOI: 10.1080/10412905.2013.767757), the essential oil from Humulus lupulus (hop) (PMID: 24152289 ), the essential oil of Piper sarmentosum (wild pepper) (0.81%) (DOI: 10.1016/S2095-3119(17)61693-9), agarwood oil (24.7% relative to total volatile compounds), spikenard (PMID: 18404340 ), and cannabis (PMID: 26657499 ). It has been shown to have a sedative effect (PMID: 18404340 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C15H24 |
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| Average Molecular Weight | 204.36 |
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| Monoisotopic Molecular Weight | 204.1878 |
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| IUPAC Name | (1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1H,1aH,2H,3H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene |
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| Traditional Name | (1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1aH,2H,3H,5H,6H,7H,7bH-cyclopropa[a]naphthalene |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@H]1CCC=C2CC[C@@H]3[C@H](C3(C)C)[C@]12C |
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| InChI Identifier | InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h7,10,12-13H,5-6,8-9H2,1-4H3/t10-,12+,13+,15+/m0/s1 |
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| InChI Key | MBIPADCEHSKJDQ-XTWPYSKKSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Aristolanes arise from the C6,C11 cyclization of the bicyclic eremophilane skeleton. |
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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 | Aristolane sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Aristolane sesquiterpenoid
- 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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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental 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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| Predicted Properties | [] |
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| General References | - Van Opstaele F, Praet T, Aerts G, De Cooman L: Characterization of novel single-variety oxygenated sesquiterpenoid hop oil fractions via headspace solid-phase microextraction and gas chromatography-mass spectrometry/olfactometry. J Agric Food Chem. 2013 Nov 6;61(44):10555-64. doi: 10.1021/jf402496t. Epub 2013 Oct 23. [PubMed:24152289 ]
- Takemoto H, Ito M, Shiraki T, Yagura T, Honda G: Sedative effects of vapor inhalation of agarwood oil and spikenard extract and identification of their active components. J Nat Med. 2008 Jan;62(1):41-6. doi: 10.1007/s11418-007-0177-0. Epub 2007 Aug 23. [PubMed:18404340 ]
- Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
- 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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