4-OH-Bz3(OH)3343
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3343_Aa_2.png?classes=border)
General Description
| Name | Value |
|---|---|
| Level | S-1 / C-1 |
| Discovered | 1990 / A. aperta |
| Synonym | AG 452 / Agel 452 |
| Molecular formula | C₂₃H₄₄N₆O₃ |
| CAS | 128549-98-4 |
| SMILES | O=C(NCCCN(O)CCCNCCCNCCCCNCCCN)C1=CC=C(O)C=C1 |
| InChI | InChI=1S/C23H44N6O3/c24-11-3-14-25-12-1-2-13-26-15-4-16-27-17-5-19-29(32)20-6-18-28-23(31)21-7-9-22(30)10-8-21/h7-10,25-27,30,32H,1-6,11-20,24H2,(H,28,31) |
| Precursor 1 [M+H]⁺ | 453.35477 |
| Precursor 2 [M+2H]²⁺ | 227.18102 |
| Precursor 3 | |
| HDX | 8 |
| Precursor HDX 1 [M(D₈)+D]⁺ | 462.41126 |
| Precursor HDX 2 [M(D₈)+2D]²⁺ | 232.21240 |
| Precursor HDX 3 | |
| Rt | 4.38 |
| Rt HDX | 3.10 |
Calculated MS/MS fragments
| # | a | b | c | ta | z | y | tz |
|---|---|---|---|---|---|---|---|
| 1 | 178.08626 | 160.07569 | 161.05971 | 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 | 276.27579 |
| 5 | 436.32822 | 418.31765 | 419.30167 | 453.35477 | 316.30709 | 299.28054 | 333.33364 |
Additional MS/MS fragments
| m/z | Annotation |
|---|---|
| 98.09643 | y2’ |
| 115.12297 | z2’ |
| 121.02841 | a0 |
| 138.05495 | ta0 |
| 259.24924 | tz4-NH₃ |
Recorded MS/MS spectra
| Precursor | Co-eluting | Spider | Source | Author | |
|---|---|---|---|---|---|
| Data | 453.35477 | A. aperta | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 227.18102 | A. aperta | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | HDX | A. aperta | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 453.35477 | A. potteri | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 227.18102 | A. potteri | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | HDX | A. potteri | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | 453.35477 | E. agrestis | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| Data | HDX | E. agrestis | Fauna Laboratories Ltd., KAZ | Y. M. Forster | |
| 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 |
|---|---|---|---|---|---|
| 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 452 | structure unknown: CI with NH₃ (ns), Amino acid analysis, Activity-studies | 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 452 | FAB-MS/MS, CI with NH₃ (ns), NMR (ns), Activity-studies | Link |
| Isolation, structure elucidation, and synthesis of novel hydroxylamine-containing polyamines from the venom of the Agelenopsis aperta spider | V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, R. A. Volkman, JACS 1990, 112, 6696-6704 | A. aperta | AG 452 | Synthesis, NMR, Amino acid analysis | Link |
| Arylamine toxins from funnel-web spider (Agelenopsis aperta) venom antagonize N-methyl-D-aspartate receptor function in mammalian brain | T. N. Parks, A. L. Mueller, L. D. Artman, B. C. Albensi, E. F. Nemeth, H. Jackson, V. J. Jasys, N. A. Saccomano, R. A. Volkmann, J. Biol. Chem. 1991, 266, 21523-21529 | A. aperta | AG 452 | 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 | A. aperta | AG 452 / Agel 452 | Review | Link |
| Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines | Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52 | A. aperta | AG 452 / Agel 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 452 | APCI-MS/MS | Link |
| Efficient and flexible solid-phase synthesis of N-hydroxypolyamine derivatives | M. Meret, S. Bienz, Eur. J. Org. Chem. 2008, 33, 5518-5525 | Agel 452 | Synthesis | 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 | 1990 / G. B. Quistad |
| Agelenopsis potteri | Agelenidae | 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 |