Record Information |
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Version | 1.0 |
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Created at | 2022-09-10 11:07:37 UTC |
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Updated at | 2022-09-10 11:07:37 UTC |
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NP-MRD ID | NP0299348 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,4r,8s,10s)-4-(2-hydroxypropan-2-yl)-9,9-dimethyl-8,10-bis(3-methylbut-2-en-1-yl)-1-(2-methylpropanoyl)-3-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-ene-7,12-dione |
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Description | GARCINIELLIPTONE L belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units. (1r,4r,8s,10s)-4-(2-hydroxypropan-2-yl)-9,9-dimethyl-8,10-bis(3-methylbut-2-en-1-yl)-1-(2-methylpropanoyl)-3-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-ene-7,12-dione is found in Garcinia subelliptica. It was first documented in 2004 (PMID: 15568764). Based on a literature review a small amount of articles have been published on GARCINIELLIPTONE L (PMID: 31862617) (PMID: 24579922). |
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Structure | CC(C)C(=O)[C@@]12C[C@H](CC=C(C)C)C(C)(C)[C@@](CC=C(C)C)(C(=O)C3=C1O[C@H](C3)C(C)(C)O)C2=O InChI=1S/C30H44O5/c1-17(2)11-12-20-16-29(23(31)19(5)6)25-21(15-22(35-25)28(9,10)34)24(32)30(26(29)33,27(20,7)8)14-13-18(3)4/h11,13,19-20,22,34H,12,14-16H2,1-10H3/t20-,22+,29-,30-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C30H44O5 |
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Average Mass | 484.6770 Da |
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Monoisotopic Mass | 484.31887 Da |
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IUPAC Name | (1R,4R,8S,10S)-4-(2-hydroxypropan-2-yl)-9,9-dimethyl-8,10-bis(3-methylbut-2-en-1-yl)-1-(2-methylpropanoyl)-3-oxatricyclo[6.3.1.0^{2,6}]dodec-2(6)-ene-7,12-dione |
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Traditional Name | (1R,4R,8S,10S)-4-(2-hydroxypropan-2-yl)-9,9-dimethyl-8,10-bis(3-methylbut-2-en-1-yl)-1-(2-methylpropanoyl)-3-oxatricyclo[6.3.1.0^{2,6}]dodec-2(6)-ene-7,12-dione |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C(=O)[C@@]12C[C@H](CC=C(C)C)C(C)(C)[C@@](CC=C(C)C)(C(=O)C3=C1O[C@H](C3)C(C)(C)O)C2=O |
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InChI Identifier | InChI=1S/C30H44O5/c1-17(2)11-12-20-16-29(23(31)19(5)6)25-21(15-22(35-25)28(9,10)34)24(32)30(26(29)33,27(20,7)8)14-13-18(3)4/h11,13,19-20,22,34H,12,14-16H2,1-10H3/t20-,22+,29-,30-/m0/s1 |
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InChI Key | VSDIWXQPEDKOLG-MBDCOTJVSA-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 monoterpenoids. Monoterpenoids are compounds containing a chain of two 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 | Monoterpenoids |
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Direct Parent | Monoterpenoids |
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Alternative Parents | |
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Substituents | - Monoterpenoid
- Cyclohexenone
- Vinylogous ester
- Tertiary alcohol
- Dihydrofuran
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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 | - Bezerra EA, Alves MMM, Amorim LV, Carvalho RCV, Cruz LPL, Costa-Junior JS, Oliveira MDDA, Lima Neto JS, Carvalho FAA, Cito AMDGL, Arcanjo DDR: Garcinielliptone FC: Selective anti-amastigote and immunomodulatory effects on macrophages infected by Leishmania amazonensis. Toxicol In Vitro. 2020 Mar;63:104750. doi: 10.1016/j.tiv.2019.104750. Epub 2019 Dec 18. [PubMed:31862617 ]
- Weng JR, Tsao LT, Wang JP, Wu RR, Lin CN: Anti-inflammatory phloroglucinols and terpenoids from Garcinia subelliptica. J Nat Prod. 2004 Nov;67(11):1796-9. doi: 10.1021/np049811x. [PubMed:15568764 ]
- Arcanjo DD, da Costa-Junior JS, Moura LH, Ferraz AB, Rossatto RR, David JM, Quintans-Junior LJ, Oliveira Rde C, Cito AM, de Oliveira AP: Garcinielliptone FC, a polyisoprenylated benzophenone from Platonia insignis Mart., promotes vasorelaxant effect on rat mesenteric artery. Nat Prod Res. 2014;28(12):923-7. doi: 10.1080/14786419.2014.889136. Epub 2014 Feb 28. [PubMed:24579922 ]
- LOTUS database [Link]
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