Record Information |
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Version | 2.0 |
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Created at | 2024-05-12 08:24:14 UTC |
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Updated at | 2024-09-03 04:21:32 UTC |
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NP-MRD ID | NP0333192 |
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Natural Product DOI | https://doi.org/10.57994/2517 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Tufnelactone A |
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Description | It was first documented in 2024 (PMID: 38734871). Based on a literature review a significant number of articles have been published on (3R,3aR,4S,11aR)-3-{[(1S,3R,4S,8R,11R,12Z,16Z,19R)-3-hydroxy-4,13-bis(hydroxymethyl)-17-methyl-9-oxo-2,10-dioxa-6-azatetracyclo[9.7.1.0³,⁸.0⁸,¹⁹]Nonadeca-12,16-dien-6-yl]methyl}-10-(hydroxymethyl)-6-methyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate (PMID: 38734870) (PMID: 38734869) (PMID: 38734867) (PMID: 38734865) (PMID: 38734862) (PMID: 38734860). |
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Structure | [H][C@@]1(CN2C[C@@H](CO)[C@]3(O)O[C@H]4C\C(C)=C\CC\C(CO)=C\[C@H]5OC(=O)[C@]3(C2)[C@]45[H])C(=O)O[C@@H]2\C=C(CO)\CC\C=C(C)\C[C@H](OC(=O)C(=C)CO)[C@@]12[H] InChI=1S/C38H51NO12/c1-21-6-4-8-24(17-41)12-29-32(28(10-21)48-34(44)23(3)16-40)27(35(45)49-29)15-39-14-26(19-43)38(47)37(20-39)33-30(50-36(37)46)13-25(18-42)9-5-7-22(2)11-31(33)51-38/h6-7,12-13,26-33,40-43,47H,3-5,8-11,14-20H2,1-2H3/b21-6+,22-7+,24-12-,25-13-/t26-,27-,28-,29+,30+,31-,32+,33-,37-,38-/m0/s1 |
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Synonyms | Value | Source |
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(3R,3AR,4S,11ar)-3-{[(1S,3R,4S,8R,11R,12Z,16Z,19R)-3-hydroxy-4,13-bis(hydroxymethyl)-17-methyl-9-oxo-2,10-dioxa-6-azatetracyclo[9.7.1.0,.0,]nonadeca-12,16-dien-6-yl]methyl}-10-(hydroxymethyl)-6-methyl-2-oxo-3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl 2-(hydroxymethyl)prop-2-enoic acid | Generator |
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Chemical Formula | C38H51NO12 |
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Average Mass | 713.8210 Da |
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Monoisotopic Mass | 713.34113 Da |
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IUPAC Name | (3R,3aR,4S,11aR)-3-{[(1S,3S,4S,8S,11R,12Z,16E,19R)-3-hydroxy-4,13-bis(hydroxymethyl)-17-methyl-9-oxo-2,10-dioxa-6-azatetracyclo[9.7.1.0^{3,8}.0^{8,19}]nonadeca-12,16-dien-6-yl]methyl}-10-(hydroxymethyl)-6-methyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate |
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Traditional Name | (3R,3aR,4S,11aR)-3-{[(1S,3S,4S,8S,11R,12Z,16E,19R)-3-hydroxy-4,13-bis(hydroxymethyl)-17-methyl-9-oxo-2,10-dioxa-6-azatetracyclo[9.7.1.0^{3,8}.0^{8,19}]nonadeca-12,16-dien-6-yl]methyl}-10-(hydroxymethyl)-6-methyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]1(CN2C[C@@H](CO)[C@]3(O)O[C@H]4C\C(C)=C\CC\C(CO)=C\[C@H]5OC(=O)[C@]3(C2)[C@]45[H])C(=O)O[C@@H]2\C=C(CO)\CC\C=C(C)\C[C@H](OC(=O)C(=C)CO)[C@@]12[H] |
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InChI Identifier | InChI=1S/C38H51NO12/c1-21-6-4-8-24(17-41)12-29-32(28(10-21)48-34(44)23(3)16-40)27(35(45)49-29)15-39-14-26(19-43)38(47)37(20-39)33-30(50-36(37)46)13-25(18-42)9-5-7-22(2)11-31(33)51-38/h6-7,12-13,26-33,40-43,47H,3-5,8-11,14-20H2,1-2H3/b21-6+,22-7+,24-12-,25-13-/t26-,27-,28-,29+,30+,31-,32+,33-,37-,38-/m0/s1 |
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InChI Key | FUPNQSIRYTXGJK-STBIJNLUSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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NOESY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | NOESY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | NOESY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | NOESY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C3D6O, experimental) | opatz@uni-mainz.de | Not Available | Not Available | 2024-05-12 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Species Name | Source | Reference |
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tufnelliae | | |
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Chemical Taxonomy |
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Classification | Not classified |
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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 | - Grundler J, Whang CH, Shin K, Savan NA, Zhong M, Saltzman WM: Modifying the Backbone Chemistry of PEG-based Bottlebrush Block Copolymers for the Formation of Long-Circulating Nanoparticles. Adv Healthc Mater. 2024 May 11:e2304040. doi: 10.1002/adhm.202304040. [PubMed:38734871 ]
- Hebdon M, Pool N, Yee R, Herrera-Theut K, Yee E, Allen LA, Hasan A, Lindenfeld J, Calhoun E, Sweitzer NK, Welling A, Breathett K: Bias in team decision-making for advanced heart failure therapies: model application. J Interprof Care. 2024 May 11:1-10. doi: 10.1080/13561820.2024.2346934. [PubMed:38734870 ]
- Nakatani S, Kawano H, Sato M, Hoshino J, Nishio S, Miura K, Sekine A, Suwabe T, Hidaka S, Kataoka H, Ishikawa E, Shimazu K, Uchiyama K, Fujimaru T, Moriyama T, Kurashige M, Shimabukuro W, Hattanda F, Kimura T, Ushio Y, Manabe S, Watanabe H, Mitobe M, Seta K, Shimada Y, Kai H, Katayama K, Ichikawa D, Hayashi H, Hanaoka K, Mochizuki T, Nakanishi K, Tsuchiya K, Horie S, Isaka Y, Muto S: Protocol for the nationwide registry of patients with polycystic kidney disease: japanese national registry of PKD (JRP). Clin Exp Nephrol. 2024 May 11. doi: 10.1007/s10157-024-02509-3. [PubMed:38734869 ]
- Nguyen PTL, Phan TAT, Vo VBN, Ngo NTN, Nguyen HT, Phung TL, Kieu MTT, Nguyen TH, Duong KNC: Medication errors in emergency departments: a systematic review and meta-analysis of prevalence and severity. Int J Clin Pharm. 2024 May 11. doi: 10.1007/s11096-024-01742-w. [PubMed:38734867 ]
- Humphrey VS, Wyant WA, Brag KO: Family planning influences and perceptions among dermatology residents from ACGME-accredited training programs: a survey-based study. Arch Dermatol Res. 2024 May 11;316(5):159. doi: 10.1007/s00403-024-02882-9. [PubMed:38734865 ]
- Zhou YB, Rezaei-Matehkolaei A, Meijer M, Kraak B, Gerrits van den Ende B, Hagen F, Afzalzadeh S, Kiasat N, Takesh A, Hoseinnejad A, Houbraken J: Aspergillus hubkae, a Novel Species Isolated from a Patient with Probable Invasive Pulmonary Aspergillosis. Mycopathologia. 2024 May 11;189(3):44. doi: 10.1007/s11046-024-00848-z. [PubMed:38734862 ]
- Kaur G, Xie C, Dong C, Najera J, Nguyen JT, Hao J: PDE4D and miR-203 are promising biomarkers for canine atopic dermatitis. Mol Biol Rep. 2024 May 11;51(1):651. doi: 10.1007/s11033-024-09605-3. [PubMed:38734860 ]
- Halle S, Hirshberg O, Manzi F, Wolinska J, Ben-Ami F: Coinfection frequency in water flea populations is a mere reflection of parasite diversity. Commun Biol. 2024 May 11;7(1):559. doi: 10.1038/s42003-024-06176-8. [PubMed:38734859 ]
- Tobaly D, Tetreault P, Cloutier G, Choiniere M, Grondin P, Freire V, Julien AS, Bureau NJ: Assessing the treatment response of lateral elbow tendinopathy using time-dependent ultrasonography, Doppler imaging, and elastography. Insights Imaging. 2024 May 11;15(1):113. doi: 10.1186/s13244-024-01695-8. [PubMed:38734857 ]
- Liu L, Du X, Qi Y, Yao L: A case of sodium bromfenac eye drop-induced toxic epidermal necrolysis and literature review. Arch Dermatol Res. 2024 May 11;316(5):167. doi: 10.1007/s00403-024-02914-4. [PubMed:38734855 ]
- Bitchagno GTM, Schuffler A, Gross J, Krumb M, Tane P, Opatz T: Sesquiterpene Lactones from Vernonia tufnelliae: Structural Characterization and Biological Evaluation. J Nat Prod. 2022 Jul 22;85(7):1681-1690. doi: 10.1021/acs.jnatprod.2c00055. Epub 2022 Jun 15. [PubMed:35704432 ]
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