IndAc3(OH)335(NMe₃)⁺
335(NMe3).png)
335(NMe3)_Aa.png?classes=border)
335(NMe3)_Ea_2.png?classes=border)
General Description
| Name | Value |
|---|---|
| Level | S-1 / C-1 |
| Discovered | 1992 / A. aperta |
| Synonym | AG 488 / AG 489a / Agel 489 / Agel 489a |
| Molecular formula | C₂₇H₄₉N₆O₂⁺ |
| CAS | 129724-53-4 |
| SMILES | O=C(NCCCN(O)CCCNCCCNCCCCC[N+](C)(C)C)CC1=CNC2=C1C=CC=C2 |
| InChI | InChI=1S/C27H48N6O2/c1-33(2,3)21-8-4-7-14-28-15-9-16-29-17-10-19-32(35)20-11-18-30-27(34)22-24-23-31-26-13-6-5-12-25(24)26/h5-6,12-13,23,28-29,31,35H,4,7-11,14-22H2,1-3H3/p+1 |
| Precursor 1 M⁺ | 489.39115 |
| Precursor 2 [M+H]²⁺ | 245.19921 |
| Precursor 3 [(M+H)+CF₃CO₂]⁺ | 603.38402 |
| HDX | 5 |
| Precursor HDX 1 M(D₅)⁺ | 494.42253 |
| Precursor HDX 2 [M(D₅)+D]²⁺ | 248.21804 |
| Precursor HDX 3 [(M(D₅)+D)+CF₃CO₂]⁺ | 609.42168 |
| Rt | 10.18 |
| Rt HDX | 8.48 |
Calculated MS/MS fragments
| # | a | b | c | ta | z | y | tz |
|---|---|---|---|---|---|---|---|
| 1 | 215.11789 | 197.10732 | 198.09134 | 248.13935 | 128.14338 | 111.11683 | 146.17775 |
| 2 | 288.17065 | 270.16009 | 271.14410 | 305.19720 | 185.20123 | 167.16685 | 203.23560 |
| 3 | 345.22850 | 327.21794 | 328.20195 | 362.25505 | 242.25907 | 223.21688 | 276.28836 |
| 4 | 430.31765 | 412.30709 | 413.29110 | 489.39115 | 315.31184 | 295.26181 | 333.34621 |
Additional MS/MS fragments
| m/z | Annotation |
|---|---|
| 126.12773 | z2-NMe₃ |
| 130.06513 | a’ |
| 183.18558 | z3-NMe₃ |
| 216.20704 | tz3-NMe₃ |
| 273.26489 | tz4-NMe₃ |
Recorded MS/MS spectra
| Precursor | Co-eluting | Spider | Source | Author | |
|---|---|---|---|---|---|
| Data | 489.39115 | A. aperta | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 245.19921 | A. aperta | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 603.38456 | A. aperta | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | HDX | A. aperta | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 489.39115 | A. potteri | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 245.19921 | A. potteri | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | HDX | A. potteri | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 489.39115 | Ariadna sp. | Spider Pharm, USA | Y. M. Forster | |
| Data | HDX | Ariadna sp. | Spider Pharm, USA | Y. M. Forster | |
| Data | 489.39115 | E. agrestis | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 245.19921 | E. agrestis | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | HDX | E. agrestis | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 489.39115 | H. curta | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 245.19921 | H. curta | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | HDX | H. curta | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 489.39115 | Hololena sp. | Spider Pharm, USA | Y. M. Forster | |
| Data | 245.19921 | Hololena sp. | Spider Pharm, USA | Y. M. Forster | |
| Data | HDX | Hololena sp. | Spider Pharm, USA | Y. M. Forster | |
| Data | 489.39115 | P. luctuosa | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 245.19921 | P. luctuosa | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | HDX | P. luctuosa | Fauna Laboratories Ltd., KAZ | Y. M. Forster |
References
| Title | Reference | Spider | Name | Content | Link |
|---|---|---|---|---|---|
| Purification and characterization of two classes of neurotoxins from the funnel web spider, Agelenopsis aperta | W. S. Skinner, M. E. Adams, G. B. Quistad, H. Kataoka, B. J. Cesarin, F. E. Enderlin, D. A. Schooley, J. Biol. Chem. 1989, 264, 2150-2155 | A. aperta | AG 488 | CI (NH₃), Amino acid analysis, Activity-studies, structure unknown | Link |
| Two classes of channel-specific toxins from funnel web spider venom | M. E. Adams, E. E. Herold, V. J. Venema, J. Comp. Physiol. 1989, 164, 333-342 | A. aperta | AG 488 | Amino acid analysis, Activity-studies, structure unknown | Link |
| Structures of paralytic acylpolyamines from the spider Agelenopsis aperta | G. B. Quistad, S. Suwanrumpha, M. Ann Jarema, M. J. Shapiro, W. S. Skinner, G. C. Jamieson, A. Lui, E. W. Fu, Biochem. Biophys. Res. Com. 1990, 169, 51-56 | A. aperta | AG 488 | FAB-MS/MS, CI (NH₃), NMR (ns), Activity-studies, wrong structure | Link |
| Novel quaternary ammonium salt-containing polyamines from the Agelenopsis aperta funnel-web spider | V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, J. T. Forman, N. A. Saccomano, J. G. Stroh, R. A. Volkmann, J. Org. Chem. 1992, 57, 1814-1820 | A. aperta | AG 489a | Synthesis, NMR | Link |
| Polyamine toxins from spiders and wasps | A. Schäfer, H. Benz, W. Fiedler, A. Guggisberg, S. Bienz, M. Hesse, The Alkaloids 1994, 45, 1-125 | A. aperta | AG 488 / AG 489a | Review | Link |
| Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines | Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52 | A. aperta | Agel 489a | Review (Agel 489A, wrong structure) | Link |
| Total synthesis of polyamine toxin HO-416b and Agel-489 using a 2-nitrobenzenesulfonamide strategy | Y. Hidai, T. Kan, T. Fukuyama, Chem. Pharm. Bull 2000, 48, 1570-1576 | Agel 489 (2) | Synthesis, NMR, FAB-MS/MS | Link | |
| Long-term potentiation in the presence of NMDA receptor antagonist arylalkylamine spider toxin | B. C. Albensi, N. Alasti, A. L. Mueller, Journal of Neuroscience Research 2000, 62, 177-185 | Agel 489 | Activity-studies | Link | |
| Low molecular mass compounds in spider venom | Y. M. Forster, S. Bienz, L. Bigler, 2020, in preparation | div. | Link |
Spider species
| Spider species | Family | Discovered |
|---|---|---|
| Agelenopsis aperta | Agelenidae | 1992 / V. J. Jasys |
| Ariadna sp. | Segestriidae | 2020 / Y. M. Forster |
| Eratigena agrestis | Agelenidae | 2020 / Y. M. Forster |
| Hololena curta | Agelenidae | 2020 / Y. M. Forster |
| Hololena sp. | Agelenidae | 2020 / Y. M. Forster |
| Pireneitega luctuosa | Agelenidae | 2020 / Y. M. Forster |