| Record Information |
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| Version | 1.0 |
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| Created at | 2021-06-20 23:37:15 UTC |
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| Updated at | 2021-06-30 00:16:31 UTC |
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| NP-MRD ID | NP0041795 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | agelasine T |
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| Provided By | JEOL Database |
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| Description | Agelasine T belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. agelasine T is found in Agelas sp. It was first documented in 2009 (PMID: 19136916). Based on a literature review a small amount of articles have been published on Agelasine T (PMID: 28389151) (PMID: 25421321). |
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| Structure | [H]O[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]1([H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])N1[C+]([H])N(C2=NC([H])=NC(N([H])[H])=C12)C([H])([H])[H])\C([H])([H])[H] InChI=1S/C26H42N5O/c1-18(11-15-31-17-30(6)23-21(31)22(27)28-16-29-23)8-9-20-25(4)13-7-12-24(2,3)19(25)10-14-26(20,5)32/h11,16-17,19-20,32H,7-10,12-15H2,1-6H3,(H2,27,28,29)/q+1/b18-11+/t19-,20+,25-,26-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C26H42N5O |
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| Average Mass | 440.6550 Da |
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| Monoisotopic Mass | 440.33839 Da |
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| IUPAC Name | 7-[(2E)-5-[(1S,2R,4aR,8aR)-2-hydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methyl-8,9-dihydro-7H-purin-8-ylium |
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| Traditional Name | 7-[(2E)-5-[(1S,2R,4aR,8aR)-2-hydroxy-2,5,5,8a-tetramethyl-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methyl-8H-purin-8-ylium |
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| CAS Registry Number | Not Available |
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| SMILES | [H]O[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]1([H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])N1[C+]([H])N(C2=NC([H])=NC(N([H])[H])=C12)C([H])([H])[H])\C([H])([H])[H] |
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| InChI Identifier | InChI=1S/C26H42N5O/c1-18(11-15-31-17-30(6)23-21(31)22(27)28-16-29-23)8-9-20-25(4)13-7-12-24(2,3)19(25)10-14-26(20,5)32/h11,16-17,19-20,32H,7-10,12-15H2,1-6H3,(H2,27,28,29)/q+1/b18-11+/t19-,20+,25-,26-/m1/s1 |
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| InChI Key | SWWWXDNTHIAEDD-TVCMIXGLSA-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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| 1D NMR | 13C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | 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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| Agelas sp. | JEOL database | - Kubota, T., et al, Tetrahedron 68, 9738 (2012)
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. |
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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 | Diterpenoids |
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| Direct Parent | Diterpenoids |
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| Alternative Parents | |
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| Substituents | - Diterpenoid
- Labdane diterpenoid
- 6-aminopurine
- Purine
- Imidazopyrimidine
- Aminopyrimidine
- Imidolactam
- Pyrimidine
- N-substituted imidazole
- Heteroaromatic compound
- Tertiary alcohol
- Imidazole
- Cyclic alcohol
- Azole
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Amine
- Alcohol
- Organic cation
- 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 | - Yamazaki H, Kanno SI, Abdjul DB, Namikoshi M: A bromopyrrole-containing diterpene alkaloid from the Okinawan marine sponge Agelas nakamurai activates the insulin pathway in Huh-7 human hepatoma cells by inhibiting protein tyrosine phosphatase 1B. Bioorg Med Chem Lett. 2017 May 15;27(10):2207-2209. doi: 10.1016/j.bmcl.2017.03.033. Epub 2017 Mar 18. [PubMed:28389151 ]
- Kang MR, Jo SA, Yoon YD, Park KH, Oh SJ, Yun J, Lee CW, Nam KH, Kim Y, Han SB, Yu J, Rho J, Kang JS: Agelasine D suppresses RANKL-induced osteoclastogenesis via down-regulation of c-Fos, NFATc1 and NF-kappaB. Mar Drugs. 2014 Nov 24;12(11):5643-56. doi: 10.3390/md12115643. [PubMed:25421321 ]
- Vik A, Proszenyak A, Vermeersch M, Cos P, Maes L, Gundersen LL: Screening of agelasine D and analogs for inhibitory activity against pathogenic protozoa; identification of hits for visceral leishmaniasis and Chagas disease. Molecules. 2009 Jan 8;14(1):279-88. doi: 10.3390/molecules14010279. [PubMed:19136916 ]
- Kubota, T., et al. (2012). Kubota, T., et al, Tetrahedron 68, 9738 (2012). Tetrahedron.
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