Record Information |
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Version | 1.0 |
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Created at | 2022-09-03 05:10:05 UTC |
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Updated at | 2022-09-03 05:10:05 UTC |
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NP-MRD ID | NP0169247 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate |
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Description | Ganoboninone D belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. methyl 3-[(1r,2r,5s,6r,10r,13s,14s)-2-hydroxy-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoate is found in Ganoderma orbiforme. It was first documented in 2022 (PMID: 36057413). Based on a literature review a significant number of articles have been published on Ganoboninone D (PMID: 36057350) (PMID: 36057373) (PMID: 36057354) (PMID: 36057321) (PMID: 36057319) (PMID: 36057231). |
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Structure | CCC(=O)CC[C@]1(C)OC[C@@]23[C@@H]1CC[C@@]2(C)C1=C(C(=O)[C@@H]3O)[C@@](C)(CCC(=O)OC)[C@@H](CC1=O)[C@@]1(C)CO1 InChI=1S/C30H42O8/c1-7-17(31)8-13-28(4)19-9-12-27(3)22-18(32)14-20(29(5)15-37-29)26(2,11-10-21(33)36-6)23(22)24(34)25(35)30(19,27)16-38-28/h19-20,25,35H,7-16H2,1-6H3/t19-,20-,25+,26+,27+,28+,29-,30+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C30H42O8 |
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Average Mass | 530.6580 Da |
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Monoisotopic Mass | 530.28797 Da |
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IUPAC Name | methyl 3-[(1R,2R,5S,6R,10R,13S,14S)-2-hydroxy-5,10,14-trimethyl-6-[(2S)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0^{1,13}.0^{4,9}]hexadec-4(9)-en-5-yl]propanoate |
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Traditional Name | methyl 3-[(1R,2R,5S,6R,10R,13S,14S)-2-hydroxy-5,10,14-trimethyl-6-[(2S)-2-methyloxiran-2-yl]-3,8-dioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0^{1,13}.0^{4,9}]hexadec-4(9)-en-5-yl]propanoate |
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CAS Registry Number | Not Available |
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SMILES | CCC(=O)CC[C@]1(C)OC[C@@]23[C@@H]1CC[C@@]2(C)C1=C(C(=O)[C@@H]3O)[C@@](C)(CCC(=O)OC)[C@@H](CC1=O)[C@@]1(C)CO1 |
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InChI Identifier | InChI=1S/C30H42O8/c1-7-17(31)8-13-28(4)19-9-12-27(3)22-18(32)14-20(29(5)15-37-29)26(2,11-10-21(33)36-6)23(22)24(34)25(35)30(19,27)16-38-28/h19-20,25,35H,7-16H2,1-6H3/t19-,20-,25+,26+,27+,28+,29-,30+/m1/s1 |
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InChI Key | WHVXPOKOWPLVPS-CAYUPQFCSA-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 fatty acid esters. These are carboxylic ester derivatives of a fatty acid. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acid esters |
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Direct Parent | Fatty acid esters |
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Alternative Parents | |
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Substituents | - Cyclohexenone
- Fatty acid ester
- Methyl ester
- Tetrahydrofuran
- Secondary alcohol
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- 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 | - Saravanan S, Carolin C F, Kumar PS, Chitra B, Rangasamy G: Biodegradation of textile dye Rhodamine-B by Brevundimonas diminuta and screening of their breakdown metabolites. Chemosphere. 2022 Aug 31;308(Pt 1):136266. doi: 10.1016/j.chemosphere.2022.136266. [PubMed:36057350 ]
- Wang J, Li T, Li M, Fu Z, Chen L, Shi D, Qiu F, Tan X: Lycopene attenuates oxidative stress-induced hepatic dysfunction of insulin signal transduction: involvement of FGF21 and mitochondria. J Nutr Biochem. 2022 Dec;110:109144. doi: 10.1016/j.jnutbio.2022.109144. Epub 2022 Aug 31. [PubMed:36057413 ]
- Kumar V, van Rensburg W, Snoep JL, Paradies HH, Borrageiro C, de Villiers C, Singh R, Joshi KB, Rautenbach M: Antimicrobial nano-assemblies of tryptocidine C, a tryptophan-rich cyclic decapeptide, from ethanolic solutions. Biochimie. 2022 Aug 31. pii: S0300-9084(22)00221-8. doi: 10.1016/j.biochi.2022.08.017. [PubMed:36057373 ]
- Prajapati S, Challis JK, Jardine TD, Brinkmann M: Levels of pesticides and trace metals in water, sediment, and fish of a large, agriculturally-dominated river. Chemosphere. 2022 Dec;308(Pt 1):136236. doi: 10.1016/j.chemosphere.2022.136236. Epub 2022 Aug 31. [PubMed:36057354 ]
- Gawthrop PJ, Pan M: Network thermodynamics of biological systems: A bond graph approach. Math Biosci. 2022 Oct;352:108899. doi: 10.1016/j.mbs.2022.108899. Epub 2022 Aug 31. [PubMed:36057321 ]
- Higuchi A, Morishita M, Nagata R, Maruoka K, Katsumi H, Yamamoto A: Functional Characterization of Extracellular Vesicles from Baker's Yeast Saccharomyces Cerevisiae as a Novel Vaccine Material for Immune Cell Maturation. J Pharm Sci. 2023 Feb;112(2):525-534. doi: 10.1016/j.xphs.2022.08.032. Epub 2022 Aug 31. [PubMed:36057319 ]
- Xie D, Mao Y, Du N, Ji H, Li J: Macrophages promote growth, migration and epithelial-mesenchymal transition of renal cell carcinoma by regulating GSDMD/IL-1beta axis. Cytokine. 2022 Nov;159:156021. doi: 10.1016/j.cyto.2022.156021. Epub 2022 Aug 31. [PubMed:36057231 ]
- Chen L, Xu W, Chen J, Zhang H, Huang X, Ma L, Yu G, Zhou Y, Ma B, Chen C, Liu Y, Ma X: Evaluating the clinical role of fibrinogen, D-dimer, mean platelet volume in patients with acute exacerbation of COPD. Heart Lung. 2023 Jan-Feb;57:54-58. doi: 10.1016/j.hrtlng.2022.08.013. Epub 2022 Aug 31. [PubMed:36057186 ]
- Deng L, Zhou ZH: Chiral Supramolecular Microporous Thio-Oxomolybdenum(V) Tartrates for the Selective Adsorptions of Gases. Inorg Chem. 2022 Sep 19;61(37):14787-14799. doi: 10.1021/acs.inorgchem.2c02283. Epub 2022 Sep 3. [PubMed:36057097 ]
- Magouliotis DE, Zotos PA, Rad AA, Koukousaki D, Vasilaki V, Portesi I, Spiliopoulos K, Athanasiou T: Meta-analysis of survival after extrapleural pneumonectomy (EPP) versus pleurectomy/decortication (P/D) for malignant pleural mesothelioma in the context of macroscopic complete resection (MCR). Updates Surg. 2022 Dec;74(6):1827-1837. doi: 10.1007/s13304-022-01369-4. Epub 2022 Sep 3. [PubMed:36057027 ]
- DeGarmo DS, Gewirtz AH, Li L, Tavalire HF, Cicchetti D: The ADAPT Parenting Intervention Benefits Combat Exposed Fathers Genetically Susceptible to Problem Drinking. Prev Sci. 2023 Jan;24(1):150-160. doi: 10.1007/s11121-022-01424-x. Epub 2022 Sep 3. [PubMed:36057024 ]
- Zhao A, Wang Q, Tuo H, Yu F, Li Y, Qi M, Zhao W: Molecular detection and characterization of Enterocytozoon bieneusi in captive alpine musk deer (Moschus chrysogaster) in Central and Eastern of Gansu Province, China. Vet Res Commun. 2022 Dec;46(4):1343-1348. doi: 10.1007/s11259-022-09992-7. Epub 2022 Sep 3. [PubMed:36057020 ]
- Katsumi S, Shinohara A, Kajiwara T, Saito M: Tension Pneumocephalus Associated with Negative Pressure Wound Therapy with Instillation and Dwell Time for Methicillin-resistant Staphylococcus aureus Infection After Spinal Deformity Surgery. Eur Spine J. 2022 Dec;31(12):3776-3781. doi: 10.1007/s00586-022-07367-9. Epub 2022 Sep 3. [PubMed:36056966 ]
- Kumar M, Dogra R, Mandal UK: Novel Formulation Approaches used for the Management of Osteoarthritis: A Recent Review. Curr Drug Deliv. 2023;20(7):841-856. doi: 10.2174/1567201819666220901092832. [PubMed:36056857 ]
- Singh C, Rao K, Yadav N, Vashist Y, Chugh P, Bansal N, Minocha N: Current Cannabidiol Safety: A Review. Curr Drug Saf. 2023;18(4):465-473. doi: 10.2174/1574886317666220902100511. [PubMed:36056846 ]
- Mota HRO, Oliveira JTA, Martins TF, Vasconcelos IM, Costa HPS, Neres DP, Silva FDA, Souza PFN: Chitinase from the Latex of Ficus benjamina L. Displays Antifungal Activity by Inducing ROS Generation and Structural Damage to the Fungal Cell Wall and Plasma Membrane. Protein Pept Lett. 2022;29(10):869-881. doi: 10.2174/0929866529666220903091107. [PubMed:36056827 ]
- Humphrey DC, Bergstrom JR, Calvo EP, Trabue SL, Scoggin KD, Greiner LL: The effect of benzoic acid with or without a direct-fed microbial on the nutrient metabolism and gas emissions of growing pigs. J Anim Sci. 2022 Nov 1;100(11):skac296. doi: 10.1093/jas/skac296. [PubMed:36056812 ]
- Wan J, Jiang Z, Liu D, Pan S, Zhou S, Liu Z: Inhibition of the glycogen synthase kinase 3beta-hypoxia-inducible factor 1alpha pathway alleviates NLRP3-mediated pyroptosis induced by high glucose in renal tubular epithelial cells. Exp Physiol. 2022 Dec;107(12):1493-1506. doi: 10.1113/EP090685. Epub 2022 Sep 26. [PubMed:36056793 ]
- Fan R, Peng X, Xie L, Dong K, Ma D, Xu W, Shi X, Zhang S, Chen J, Yu X, Yang Y: Importance of Bmal1 in Alzheimer's disease and associated aging-related diseases: Mechanisms and interventions. Aging Cell. 2022 Oct;21(10):e13704. doi: 10.1111/acel.13704. Epub 2022 Sep 3. [PubMed:36056774 ]
- Smith IT, Zhang E, Yildirim YA, Campos MA, Abdel-Mottaleb M, Yildirim B, Ramezani Z, Andre VL, Scott-Vandeusen A, Liang P, Khizroev S: Nanomedicine and nanobiotechnology applications of magnetoelectric nanoparticles. Wiley Interdiscip Rev Nanomed Nanobiotechnol. 2023 Mar;15(2):e1849. doi: 10.1002/wnan.1849. Epub 2022 Sep 3. [PubMed:36056752 ]
- LOTUS database [Link]
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