Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 02:08:19 UTC |
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Updated at | 2022-09-11 02:08:19 UTC |
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NP-MRD ID | NP0308394 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,2r,4ar,5r,5'r,8as)-5'-(furan-3-yl)-5,8a-dihydroxy-4a,5-bis(hydroxymethyl)-2-methyl-tetrahydro-2h-spiro[naphthalene-1,3'-oxolane]-2',4-dione |
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Description | Sandrasin B belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,2r,4ar,5r,5'r,8as)-5'-(furan-3-yl)-5,8a-dihydroxy-4a,5-bis(hydroxymethyl)-2-methyl-tetrahydro-2h-spiro[naphthalene-1,3'-oxolane]-2',4-dione is found in Teucrium sandrasicum. It was first documented in 2022 (PMID: 36137741). Based on a literature review a significant number of articles have been published on Sandrasin B (PMID: 36137648) (PMID: 36137641) (PMID: 36137593) (PMID: 36137590). |
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Structure | C[C@@H]1CC(=O)[C@@]2(CO)[C@@](O)(CO)CCC[C@@]2(O)[C@@]11C[C@@H](OC1=O)C1=COC=C1 InChI=1S/C20H26O8/c1-12-7-15(23)19(11-22)17(25,10-21)4-2-5-20(19,26)18(12)8-14(28-16(18)24)13-3-6-27-9-13/h3,6,9,12,14,21-22,25-26H,2,4-5,7-8,10-11H2,1H3/t12-,14-,17+,18+,19+,20-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C20H26O8 |
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Average Mass | 394.4200 Da |
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Monoisotopic Mass | 394.16277 Da |
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IUPAC Name | (1R,2R,4aR,5R,5'R,8aS)-5'-(furan-3-yl)-5,8a-dihydroxy-4a,5-bis(hydroxymethyl)-2-methyl-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-2',4-dione |
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Traditional Name | (1R,2R,4aR,5R,5'R,8aS)-5'-(furan-3-yl)-5,8a-dihydroxy-4a,5-bis(hydroxymethyl)-2-methyl-tetrahydro-2H-spiro[naphthalene-1,3'-oxolane]-2',4-dione |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1CC(=O)[C@@]2(CO)[C@@](O)(CO)CCC[C@@]2(O)[C@@]11C[C@@H](OC1=O)C1=COC=C1 |
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InChI Identifier | InChI=1S/C20H26O8/c1-12-7-15(23)19(11-22)17(25,10-21)4-2-5-20(19,26)18(12)8-14(28-16(18)24)13-3-6-27-9-13/h3,6,9,12,14,21-22,25-26H,2,4-5,7-8,10-11H2,1H3/t12-,14-,17+,18+,19+,20-/m1/s1 |
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InChI Key | RXDUFGKJOZHMHQ-AYSXHUKSSA-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 diterpene lactones. These are diterpenoids containing a lactone moiety. |
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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 | Terpene lactones |
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Direct Parent | Diterpene lactones |
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Alternative Parents | |
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Substituents | - Diterpene lactone
- Diterpenoid
- Clerodane diterpenoid
- Gamma butyrolactone
- Cyclic alcohol
- Heteroaromatic compound
- Furan
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Ketone
- Lactone
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic 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 | - Plantone D, Locci S, Bergantini L, Manco C, Cortese R, Meocci M, Cavallaro D, d'Alessandro M, Bargagli E, De Stefano N: Brain neuronal and glial damage during acute COVID-19 infection in absence of clinical neurological manifestations. J Neurol Neurosurg Psychiatry. 2022 Sep 22. pii: jnnp-2022-329933. doi: 10.1136/jnnp-2022-329933. [PubMed:36137741 ]
- Li D, Que Y, Ding S, Hu G, Wang W, Mao X, Wang Y, Li C, Huang L, Zhou J, Zhang W, Xiao M: Anti-BCMA CAR-T cells therapy for a patient with extremely high membrane BCMA expression: a case report. J Immunother Cancer. 2022 Sep;10(9):e005403. doi: 10.1136/jitc-2022-005403. [PubMed:36137648 ]
- Kunitomo K, Shimizu T, Tsuji T, Inoue Y: Hyperintense central pontine lesion in intravascular large B-cell lymphoma. BMJ Case Rep. 2022 Sep 22;15(9):e250945. doi: 10.1136/bcr-2022-250945. [PubMed:36137641 ]
- Godet C, Cadranel J, Frat JP, Ragot S, Couturaud F: Reply to: Nebulised liposomal amphotericin-B: a promising strategy for preventing ABPA relapse. Eur Respir J. 2022 Nov 24;60(5):2201678. doi: 10.1183/13993003.01678-2022. Print 2022 Nov. [PubMed:36137593 ]
- Son K, Jamil R, Chowdhury A, Mukherjee M, Venegas C, Miyasaki K, Zhang K, Patel Z, Salter B, Yuen ACY, Lau KS, Cowbrough B, Radford K, Huang C, Kjarsgaard M, Dvorkin-Gheva A, Smith J, Li QZ, Waserman S, Ryerson CJ, Nair P, Ho T, Balakrishnan N, Nazy I, Bowdish DM, Svenningsen S, Carlsten C, Mukherjee M: Circulating anti-nuclear autoantibodies in COVID-19 survivors predict long-COVID symptoms. Eur Respir J. 2022 Sep 22:2200970. doi: 10.1183/13993003.00970-2022. [PubMed:36137590 ]
- LOTUS database [Link]
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