Record Information |
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Version | 1.0 |
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Created at | 2022-09-06 06:35:34 UTC |
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Updated at | 2022-09-06 06:35:34 UTC |
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NP-MRD ID | NP0227306 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 8-(5,6-dimethylhept-3-en-2-yl)-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-4-en-3-one |
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Description | Gargalol B belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position. 8-(5,6-dimethylhept-3-en-2-yl)-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-4-en-3-one is found in Grifola gargal. It was first documented in 2022 (PMID: 36088043). Based on a literature review a significant number of articles have been published on Gargalol B (PMID: 36087927) (PMID: 36087886) (PMID: 36087866) (PMID: 36087840). |
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Structure | CC(C)C(C)C=CC(C)C1CCC2=C3C(=O)CC45CC(O)CCC4(C)C3(CCC12C)OO5 InChI=1S/C28H42O4/c1-17(2)18(3)7-8-19(4)21-9-10-22-24-23(30)16-27-15-20(29)11-12-26(27,6)28(24,32-31-27)14-13-25(21,22)5/h7-8,17-21,29H,9-16H2,1-6H3 |
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Synonyms | Not Available |
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Chemical Formula | C28H42O4 |
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Average Mass | 442.6400 Da |
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Monoisotopic Mass | 442.30831 Da |
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IUPAC Name | 8-(5,6-dimethylhept-3-en-2-yl)-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0^{1,13}.0^{4,12}.0^{5,9}]nonadec-4-en-3-one |
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Traditional Name | 8-(5,6-dimethylhept-3-en-2-yl)-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0^{1,13}.0^{4,12}.0^{5,9}]nonadec-4-en-3-one |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C(C)C=CC(C)C1CCC2=C3C(=O)CC45CC(O)CCC4(C)C3(CCC12C)OO5 |
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InChI Identifier | InChI=1S/C28H42O4/c1-17(2)18(3)7-8-19(4)21-9-10-22-24-23(30)16-27-15-20(29)11-12-26(27,6)28(24,32-31-27)14-13-25(21,22)5/h7-8,17-21,29H,9-16H2,1-6H3 |
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InChI Key | LJBJXGTWGWODIW-UHFFFAOYSA-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 ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Ergostane steroids |
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Direct Parent | Ergostane steroids |
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Alternative Parents | |
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Substituents | - Ergostane-skeleton
- Cyclic alcohol
- Ortho-dioxolane
- Dialkyl peroxide
- Secondary alcohol
- 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 | - Motahari Rad H, Mowla SJ, Ramazanali F, Rezazadeh Valojerdi M: Characterization of altered microRNAs related to different phenotypes of polycystic ovarian syndrome (PCOS) in serum, follicular fluid, and cumulus cells. Taiwan J Obstet Gynecol. 2022 Sep;61(5):768-779. doi: 10.1016/j.tjog.2022.05.013. [PubMed:36088043 ]
- Pontrelli G, Huscher C, Scioscia M, Brusca F, Tedeschi U, Greco P, Mancarella M, Biglia N, Novara L: End-to-end versus side-to-end anastomosis after bowel resection for deep infiltrating endometriosis: a retrospective study. J Gynecol Obstet Hum Reprod. 2022 Sep 7:102472. doi: 10.1016/j.jogoh.2022.102472. [PubMed:36087927 ]
- Qi H, Cai H, Liu X, Liu S, Ding C, Xu M: The cytokinin type-B response regulator PeRR12 is a negative regulator of adventitious rooting and salt tolerance in poplar. Plant Sci. 2022 Sep 7:111456. doi: 10.1016/j.plantsci.2022.111456. [PubMed:36087886 ]
- Shah L, Latif A, Williams KJ, Tirella A: Role of stiffness and physico-chemical properties of tumour microenvironment on breast cancer cell stemness. Acta Biomater. 2022 Sep 7. pii: S1742-7061(22)00557-8. doi: 10.1016/j.actbio.2022.08.074. [PubMed:36087866 ]
- Temme JS, Crainic JA, Walker LM, Yang W, Tan Z, Huang X, Gildersleeve JC: Microarray-guided evaluation of the frequency, B cell origins, and selectivity of human glycan-binding antibodies reveals new insights and novel antibodies. J Biol Chem. 2022 Sep 7:102468. doi: 10.1016/j.jbc.2022.102468. [PubMed:36087840 ]
- LOTUS database [Link]
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