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2,5-(OH)₂-Bz33343
General Description
| Name | Value |
|---|
| Level | S-1 / C-3 |
| Discovered | 1991 / H. curta |
| Synonym | AG 452a / HO 452 |
| Molecular formula | C₂₃H₄₄N₆O₃ |
| CAS | 133805-35-3 |
| SMILES | O=C(C1=C(O)C=CC(O)=C1)NCCCNCCCNCCCNCCCCNCCCN |
| InChI | InChI=1S/C23H44N6O3/c24-9-3-12-25-10-1-2-11-26-13-4-14-27-15-5-16-28-17-6-18-29-23(32)21-19-20(30)7-8-22(21)31/h7-8,19,25-28,30-31H,1-6,9-18,24H2,(H,29,32) |
| |
| Precursor 1 [M+H]⁺ | 453.35477 |
| Precursor 2 [M+2H]²⁺ | 227.18102 |
| Precursor 3 | |
| |
| HDX | 9 |
| Precursor HDX 1 [M(D₉)+D]⁺ | 463.41753 |
| Precursor HDX 2 [M(D₉)+2D]²⁺ | 232.71554 |
| Precursor HDX 3 | |
| |
| Rt | 4.80 |
| Rt HDX | 3.45 |
Calculated MS/MS fragments
| # | a | b | c | ta | z | y | tz |
|---|
| 1 | 194.08117 | 176.07060 | 177.05462 | 211.10772 | 58.06513 | 41.03858 | 75.09167 |
| 2 | 251.13902 | 233.12845 | 234.11247 | 268.16557 | 129.13862 | 112.11208 | 146.16517 |
| 3 | 308.19687 | 290.18630 | 291.17032 | 325.22342 | 186.19647 | 169.16993 | 203.22302 |
| 4 | 379.27037 | 361.25980 | 362.24382 | 396.29692 | 243.25432 | 226.22777 | 260.28087 |
| 5 | 436.32822 | 418.31765 | 419.30167 | 453.35477 | 300.31217 | 283.28562 | 317.33872 |
Additional MS/MS fragments
Recorded MS/MS spectra
| pdf | Precursor | Co-eluting | Spider | Source | Author |
|---|
| Data | 453.35477 | | H. curta | Fauna Laboratories Ltd., KAZ | Y. M. Forster |
| Data | 227.18102 | | H. curta | Fauna Laboratories Ltd., KAZ | Y. M. Forster |
| Data | HDX | | H. curta | Fauna Laboratories Ltd., KAZ | Y. M. Forster |
| Data | 453.35477 | | Hololena sp. | Spider Pharm, USA | Y. M. Forster |
| Data | 227.18102 | | Hololena sp. | Spider Pharm, USA | Y. M. Forster |
| Data | HDX | | Hololena sp. | Spider Pharm, USA | Y. M. Forster |
References
| Title | Reference | Spider | Name | Content | Link |
|---|
| Paralytic and insecticidal toxins from the funnel web spider, Hololena curta | G. B. Quistad, C. C. Reuter, W. S. Skinner, P. A. Dennis, S. Suwanrumpha, E. W. Fu, Toxicon 1991, 29, 329-336 | H. curta | HO 452 | FAB-MS/MS (ns), Activity-studies | 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 | H. curta | HO 452 | Review | Link |
| Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines | Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52 | H. curta | HO 452 | Review | Link |
| The acylpolyamines from the venom of the spider Agelenopsis aperta | S. Chesnov, L. Bigler, M. Hesse, Helv. Chim. Acta 2001, 84, 2178-2197 | A. aperta | AG 452a | APCI-MS/MS | Link |
| Development of a high-resolution MS-based method for the structural elucidation of polyamine spider toxins | S. Eichenberger, PhD-Thesis, University of Zurich 2009, 1-156 | A. aperta | AG 452a | APCI reduction artefact | Link |
| Structure-activity relationship studies of N-methylated and N-hydroxylated spider polyamine toxins as inhibitors of ionotropic glutamate receptors | N. G. Norager, M. H. Poulson, A. G. Jensen, N. S. Jeppesen, A. S. Kristensen, K. Strømgaard, J. Med. Chem. 2014, 57, 4940-4949 | | (33c) | Synthesis, NMR, 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 |
|---|
| Hololena curta | Agelenidae | 1991 / G. B. Quistad |
| Hololena sp. | Agelenidae | 2020 / Y. M. Forster |
The presence of AG 452a in the venom of Agelenopsis aperta (Chesnov, 2001) was refuted (Eichenberger, 2009).