Record Information |
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Version | 1.0 |
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Created at | 2020-09-23 01:59:07 UTC |
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Updated at | 2021-08-10 02:55:48 UTC |
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NP-MRD ID | NP0001625 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Demethylasterriquinone B1 |
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Provided By | NPAtlas |
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Description | Demethylasterriquinone B1, also known as DMAQB-1, belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. Demethylasterriquinone B1 is found in Pseudomassaria and Pseudomassaria sp.. It was first documented in 1999 (PMID: 10320380). Based on a literature review a significant number of articles have been published on Demethylasterriquinone B1 (PMID: 30574832) (PMID: 29526571) (PMID: 17595071) (PMID: 17240464). |
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Structure | [H]OC1=C(C2=C([H])N([H])C3=C(C([H])=C([H])C([H])=C23)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C(=O)C(O[H])=C(C2=C(N([H])C3=C([H])C([H])=C([H])C([H])=C23)C(C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=O InChI=1S/C32H30N2O4/c1-6-32(4,5)31-23(20-11-7-8-13-22(20)34-31)25-29(37)27(35)24(28(36)30(25)38)21-16-33-26-18(15-14-17(2)3)10-9-12-19(21)26/h6-14,16,33-35,38H,1,15H2,2-5H3 |
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Synonyms | Value | Source |
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DMAQB-1 | HMDB | Demethyl-asterriquinone b1 | HMDB | Demethylasterriquinone b-1 | HMDB |
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Chemical Formula | C32H30N2O4 |
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Average Mass | 506.6020 Da |
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Monoisotopic Mass | 506.22056 Da |
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IUPAC Name | 2,5-dihydroxy-3-[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]-6-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione |
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Traditional Name | 2,5-dihydroxy-3-[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]-6-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C(C2=C([H])N([H])C3=C(C([H])=C([H])C([H])=C23)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C(=O)C(O[H])=C(C2=C(N([H])C3=C([H])C([H])=C([H])C([H])=C23)C(C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=O |
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InChI Identifier | InChI=1S/C32H30N2O4/c1-6-32(4,5)31-23(20-11-7-8-13-22(20)34-31)25-29(37)27(35)24(28(36)30(25)38)21-16-33-26-18(15-14-17(2)3)10-9-12-19(21)26/h6-14,16,33-35,38H,1,15H2,2-5H3 |
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InChI Key | XMGNJVXBPZAETK-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, 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 prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. |
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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 | Quinone and hydroquinone lipids |
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Direct Parent | Prenylquinones |
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Alternative Parents | |
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Substituents | - Prenylbenzoquinone
- Indole
- Indole or derivatives
- P-benzoquinone
- Quinone
- Benzenoid
- Substituted pyrrole
- Heteroaromatic compound
- Pyrrole
- Vinylogous acid
- Ketone
- Cyclic ketone
- Azacycle
- Enol
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- 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 | - Zhang B, Salituro G, Szalkowski D, Li Z, Zhang Y, Royo I, Vilella D, Diez MT, Pelaez F, Ruby C, Kendall RL, Mao X, Griffin P, Calaycay J, Zierath JR, Heck JV, Smith RG, Moller DE: Discovery of a small molecule insulin mimetic with antidiabetic activity in mice. Science. 1999 May 7;284(5416):974-7. doi: 10.1126/science.284.5416.974. [PubMed:10320380 ]
- Beard RS Jr, Hoettels BA, Meegan JE, Wertz TS, Cha BJ, Yang X, Oxford JT, Wu MH, Yuan SY: AKT2 maintains brain endothelial claudin-5 expression and selective activation of IR/AKT2/FOXO1-signaling reverses barrier dysfunction. J Cereb Blood Flow Metab. 2020 Feb;40(2):374-391. doi: 10.1177/0271678X18817512. Epub 2018 Dec 21. [PubMed:30574832 ]
- Deng T, Zhang Y, Wu Y, Ma P, Duan J, Qin W, Yang X, Chen M: Dibutyl phthalate exposure aggravates type 2 diabetes by disrupting the insulin-mediated PI3K/AKT signaling pathway. Toxicol Lett. 2018 Jun 15;290:1-9. doi: 10.1016/j.toxlet.2018.03.004. Epub 2018 Mar 8. [PubMed:29526571 ]
- Kim H, Deng L, Xiong X, Hunter WD, Long MC, Pirrung MC: Glyceraldehyde 3-phosphate dehydrogenase is a cellular target of the insulin mimic demethylasterriquinone B1. J Med Chem. 2007 Jul 26;50(15):3423-6. doi: 10.1021/jm070437i. Epub 2007 Jun 27. [PubMed:17595071 ]
- Shah DI, Singh M: Effect of demethylasterriquinone b1 in hypertension associated vascular endothelial dysfunction. Int J Cardiol. 2007 Sep 3;120(3):317-24. doi: 10.1016/j.ijcard.2006.10.006. Epub 2007 Jan 22. [PubMed:17240464 ]
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