Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 09:28:56 UTC |
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Updated at | 2022-04-28 09:28:56 UTC |
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NP-MRD ID | NP0065237 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Grindelic acid |
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Description | Grindelic acid, also known as grindelate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Grindelic acid is found in Ericameria paniculata, Grindelia camporum , Grindelia hirsutula, Grindelia integrifolia, Grindelia nana, Grindelia paludosa, Grindelia robusta, Grindelia stricta, Isocoma tenuisecta and Xanthocephalum gymnospermoides. It was first documented in 2005 (PMID: 16010831). Based on a literature review a small amount of articles have been published on Grindelic acid (PMID: 33536899) (PMID: 31644941) (PMID: 26119826) (PMID: 23831507). |
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Structure | CC1=CC[C@H]2C(C)(C)CCC[C@]2(C)[C@@]11CC[C@@](C)(CC(O)=O)O1 InChI=1S/C20H32O3/c1-14-7-8-15-17(2,3)9-6-10-19(15,5)20(14)12-11-18(4,23-20)13-16(21)22/h7,15H,6,8-13H2,1-5H3,(H,21,22)/t15-,18-,19-,20+/m0/s1 |
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Synonyms | Value | Source |
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Grindelate | Generator |
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Chemical Formula | C20H32O3 |
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Average Mass | 320.4730 Da |
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Monoisotopic Mass | 320.23514 Da |
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IUPAC Name | 2-[(1R,4aS,5'S,8aS)-2,5,5,5',8a-pentamethyl-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-yl]acetic acid |
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Traditional Name | (1R,4aS,5'S,8aS)-2,5,5,5',8a-pentamethyl-4a,6,7,8-tetrahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-ylacetic acid |
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CAS Registry Number | Not Available |
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SMILES | CC1=CC[C@H]2C(C)(C)CCC[C@]2(C)[C@@]11CC[C@@](C)(CC(O)=O)O1 |
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InChI Identifier | InChI=1S/C20H32O3/c1-14-7-8-15-17(2,3)9-6-10-19(15,5)20(14)12-11-18(4,23-20)13-16(21)22/h7,15H,6,8-13H2,1-5H3,(H,21,22)/t15-,18-,19-,20+/m0/s1 |
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InChI Key | XLWWERNKTLITEF-MVJPYGJCSA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 diterpenoids. These are terpene compounds formed by four 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 | Diterpenoids |
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Direct Parent | Diterpenoids |
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Alternative Parents | |
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Substituents | - Diterpenoid
- Grindelane diterpenoid
- Tetrahydrofuran
- Carboxylic acid derivative
- Carboxylic acid
- Dialkyl ether
- Ether
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Oxacycle
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- 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 | - Gierlikowska B, Filipek A, Gierlikowski W, Kania D, Stefanska J, Demkow U, Kiss AK: Grindelia squarrosa Extract and Grindelic Acid Modulate Pro-inflammatory Functions of Respiratory Epithelium and Human Macrophages. Front Pharmacol. 2021 Jan 18;11:534111. doi: 10.3389/fphar.2020.534111. eCollection 2020. [PubMed:33536899 ]
- Gierlikowska B, Gierlikowski W, Bekier K, Skalicka-Wozniak K, Czerwinska ME, Kiss AK: Inula helenium and Grindelia squarrosa as a source of compounds with anti-inflammatory activity in human neutrophils and cultured human respiratory epithelium. J Ethnopharmacol. 2020 Mar 1;249:112311. doi: 10.1016/j.jep.2019.112311. Epub 2019 Oct 20. [PubMed:31644941 ]
- Zerbe P, Rodriguez SM, Mafu S, Chiang A, Sandhu HK, O'Neil-Johnson M, Starks CM, Bohlmann J: Exploring diterpene metabolism in non-model species: transcriptome-enabled discovery and functional characterization of labda-7,13E-dienyl diphosphate synthase from Grindelia robusta. Plant J. 2015 Sep;83(5):783-93. doi: 10.1111/tpj.12925. Epub 2015 Jul 23. [PubMed:26119826 ]
- Reta GF, Chiaramello AI, Garcia C, Leon LG, Martin VS, Padron JM, Tonn CE, Donadel OJ: Derivatives of grindelic acid: from a non-active natural diterpene to synthetic antitumor derivatives. Eur J Med Chem. 2013 Sep;67:28-38. doi: 10.1016/j.ejmech.2013.06.013. Epub 2013 Jun 18. [PubMed:23831507 ]
- Orden AA, Cifuente DA, Borkowski EJ, Tonn CE, Sanz MK: Stereo- and regioselective hydroxylation of grindelic acid derivatives by Aspergillus niger. Nat Prod Res. 2005 Sep;19(6):625-31. doi: 10.1080/14786410512331330693. [PubMed:16010831 ]
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