| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-06 14:06:36 UTC |
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| Updated at | 2022-09-06 14:06:36 UTC |
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| NP-MRD ID | NP0232766 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1r,2s,4r,6r,7s,8s)-8-isopropyl-1-methyl-3-methylidenetricyclo[4.4.0.0²,⁷]decan-4-ol |
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| Description | Lemnalol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,2s,4r,6r,7s,8s)-8-isopropyl-1-methyl-3-methylidenetricyclo[4.4.0.0²,⁷]decan-4-ol is found in Marsupella aquatica. (1r,2s,4r,6r,7s,8s)-8-isopropyl-1-methyl-3-methylidenetricyclo[4.4.0.0²,⁷]decan-4-ol was first documented in 2010 (PMID: 20190445). Based on a literature review a small amount of articles have been published on Lemnalol (PMID: 31671563) (PMID: 25557511) (PMID: 23306170) (PMID: 22067479). |
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| Structure | CC(C)[C@@H]1CC[C@]2(C)[C@@H]3C[C@@H](O)C(=C)[C@H]2[C@@H]13 InChI=1S/C15H24O/c1-8(2)10-5-6-15(4)11-7-12(16)9(3)14(15)13(10)11/h8,10-14,16H,3,5-7H2,1-2,4H3/t10-,11+,12+,13-,14-,15+/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C15H24O |
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| Average Mass | 220.3560 Da |
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| Monoisotopic Mass | 220.18272 Da |
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| IUPAC Name | (1R,2S,4R,6R,7S,8S)-1-methyl-3-methylidene-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]decan-4-ol |
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| Traditional Name | (1R,2S,4R,6R,7S,8S)-8-isopropyl-1-methyl-3-methylidenetricyclo[4.4.0.0^{2,7}]decan-4-ol |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)[C@@H]1CC[C@]2(C)[C@@H]3C[C@@H](O)C(=C)[C@H]2[C@@H]13 |
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| InChI Identifier | InChI=1S/C15H24O/c1-8(2)10-5-6-15(4)11-7-12(16)9(3)14(15)13(10)11/h8,10-14,16H,3,5-7H2,1-2,4H3/t10-,11+,12+,13-,14-,15+/m0/s1 |
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| InChI Key | LPXOPRGPLUWGKB-VRPMWHRCSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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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 | - Copaane sesquiterpenoid
- Sesquiterpenoid
- 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 | Not Available |
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| Physical Properties |
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| State | Not Available |
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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 | - Tai BY, Wen ZH, Cheng PY, Yang HY, Duh CY, Chen PN, Hsu CH: Lemnalol Modulates the Electrophysiological Characteristics and Calcium Homeostasis of Atrial Myocytes. Mar Drugs. 2019 Oct 30;17(11):619. doi: 10.3390/md17110619. [PubMed:31671563 ]
- Lee HP, Lin YY, Duh CY, Huang SY, Wang HM, Wu SF, Lin SC, Jean YH, Wen ZH: Lemnalol attenuates mast cell activation and osteoclast activity in a gouty arthritis model. J Pharm Pharmacol. 2015 Feb;67(2):274-85. doi: 10.1111/jphp.12331. Epub 2014 Dec 31. [PubMed:25557511 ]
- Lee HP, Huang SY, Lin YY, Wang HM, Jean YH, Wu SF, Duh CY, Wen ZH: Soft coral-derived lemnalol alleviates monosodium urate-induced gouty arthritis in rats by inhibiting leukocyte infiltration and iNOS, COX-2 and c-Fos protein expression. Mar Drugs. 2013 Jan 10;11(1):99-113. doi: 10.3390/md11010099. [PubMed:23306170 ]
- Lin YC, Huang SY, Jean YH, Chen WF, Sung CS, Kao ES, Wang HM, Chakraborty C, Duh CY, Wen ZH: Intrathecal lemnalol, a natural marine compound obtained from Formosan soft coral, attenuates nociceptive responses and the activity of spinal glial cells in neuropathic rats. Behav Pharmacol. 2011 Dec;22(8):739-50. doi: 10.1097/FBP.0b013e32834d0ecb. [PubMed:22067479 ]
- Cheng SY, Lin EH, Huang JS, Wen ZH, Duh CY: Ylangene-type and nardosinane-type sesquiterpenoids from the soft corals Lemnalia flava and Paralemnalia thyrsoides. Chem Pharm Bull (Tokyo). 2010 Mar;58(3):381-5. doi: 10.1248/cpb.58.381. [PubMed:20190445 ]
- LOTUS database [Link]
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