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IndAc3(OH)3343

General Description

NameValue
LevelS-1 / C-1
Discovered1990 / A. aperta
SynonymAG 489 / Agatoxin 489 / Agel 489 / HO 489
Molecular formulaC₂₆H₄₇N₇O₂
CAS128549-96-2
SMILESO=C(NCCCN(O)CCCNCCCNCCCCNCCCN)CC1=CNC2=C1C=CC=C2
InChIInChI=1S/C26H47N7O2/c27-11-5-14-28-12-3-4-13-29-15-6-16-30-17-7-19-33(35)20-8-18-31-26(34)21-23-22-32-25-10-2-1-9-24(23)25/h1-2,9-10,22,28-30,32,35H,3-8,11-21,27H2,(H,31,34)
Precursor 1 [M+H]⁺490.38640
Precursor 2 [M+2H]²⁺245.69684
Precursor 3
HDX8
Precursor HDX 1 [M(D₈)+D]⁺499.44289
Precursor HDX 2 [M(D₈)+2D]²⁺250.72822
Precursor HDX 3
Rt9.06
Rt HDX7.28

Calculated MS/MS fragments

#abctazytz
1215.11789197.10732198.09134248.1393558.0651341.0385875.09167
2288.17065270.16009271.14410305.19720129.13862112.11208146.16517
3345.22850327.21794328.20195362.25505186.19647169.16993203.22302
4416.30200398.29144399.27545433.32855243.25432226.22777276.27579
5473.35985455.34929456.33330490.38640316.30709299.28054333.33364

Additional MS/MS fragments

m/zAnnotation
130.06513a’
158.06004a0
175.08659ta0

Recorded MS/MS spectra

pdfPrecursorCo-elutingSpiderSourceAuthor
Data490.38640A. apertaFauna Laboratories Ltd., KAZY. M. Forster
Data245.69684A. apertaFauna Laboratories Ltd., KAZY. M. Forster
DataHDXA. apertaFauna Laboratories Ltd., KAZY. M. Forster
Data490.38640A. potteriFauna Laboratories Ltd., KAZY. M. Forster
Data245.69684A. potteriFauna Laboratories Ltd., KAZY. M. Forster
DataHDXA. potteriFauna Laboratories Ltd., KAZY. M. Forster
Data490.38640Ariadna sp.Spider Pharm, USAY. M. Forster
DataHDXAriadna sp.Spider Pharm, USAY. M. Forster
Data490.38640H. curtaFauna Laboratories Ltd., KAZY. M. Forster
Data245.69684H. curtaFauna Laboratories Ltd., KAZY. M. Forster
DataHDXH. curtaFauna Laboratories Ltd., KAZY. M. Forster
Data490.38640Hololena sp.Spider Pharm, USAY. M. Forster
Data245.69684Hololena sp.Spider Pharm, USAY. M. Forster
DataHDXHololena sp.Spider Pharm, USAY. M. Forster

References

TitleReferenceSpiderNameContentLink
Purification and characterization of two classes of neurotoxins from the funnel web spider, Agelenopsis apertaW. S. Skinner, M. E. Adams, G. B. Quistad, H. Kataoka, B. J. Cesarin, F. E. Enderlin, D. A. Schooley, J. Biol. Chem. 1989, 264, 2150-2155A. apertaAG 489CI (NH₃), Amino acid analysis, Activity-studies, structure unknownLink
Two classes of channel-specific toxins from funnel web spider venomM. E. Adams, E. E. Herold, V. J. Venema, J. Comp. Physiol. 1989, 164, 333-342A. apertaAG 489Amino acid analysis, Activity-studies, structure unknownLink
Isolation, structure elucidation, and synthesis of novel hydroxylamine-containing polyamines from the venom of the Agelenopsis aperta spiderV. 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, 6696-6704A. apertaAG 489Synthesis, NMR, Amino acid analysisLink
Structures of paralytic acylpolyamines from the spider Agelenopsis apertaG. 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, 51-56A. apertaAG 489FAB-MS/MS, CI (NH₃), NMR (ns), Activity-studiesLink
Paralytic and insecticidal toxins from the funnel web spider, Hololena curtaG. B. Quistad, C. C. Reuter, W. S. Skinner, P. A. Dennis, S. Suwanrumpha, E. W. Fu, Toxicon 1991, 29, 329-336H. curtaHO 489FAB-MS/MS (ns), Activity-studiesLink
Arylamine toxins from funnel-web spider (Agelenopsis aperta) venom antagonize N-methyl-D-aspartate receptor function in mammalian brainT. 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, 21523-21529A. apertaAG 489Activity-studiesLink
A highly potent and selective N-methyl-D-aspartate receptor antagonist from the venom of the Agelenopsis aperta spiderN. I. Kiskin, I. V. Chizhmakov, A. Ya. Tsyndrenko, A. L. Mueller, H. Jackson, O. A. Krishtal, Neuroscience 1992, 51, 11-18A. apertaAgatoxin 489Activity-studiesLink
Anesthesia and muscle relaxation with intrathecal injection of AR636 and AG489, two acylpolyamine spider toxins, in ratE. E. Herold, T. L. Yaksh, Anesthesiology 1992, 77, 507-512A. apertaAG 489Activity-studiesLink
Effects of Agelenopsis aperta toxins on the N-methyl-D-aspartate receptor: Polyamine-like and high-affinity antagonist actionsK. Williams, J. Pharmacol. Exp. Ther. 1993, 266, 231-236Agel 489Activity-studiesLink
Polyamine toxins from spiders and waspsA. Schäfer, H. Benz, W. Fiedler, A. Guggisberg, S. Bienz, M. Hesse, The Alkaloids 1994, 45, 1-125A. aperta & H. curtaAG 489 / Agel 489 / HO 489ReviewLink
Pharmacology of polyamine toxins from spider and waspsA. L. Mueller, R. Roeloffs, H. Jackson, The Alkaloids, Chapter 2 1995, 46, 63-94A. apertaAgel 489ReviewLink
Block of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors by polyamines and polyamine toxinsM. S. Washburn, R. Dingledine, J. Pharmacol. Exp. Ther. 1996, 278, 669-678Agel 489Activity-studiesLink
The spider Paracoelotes birulai: Detection and structural elucidation of new acylpolyamines by on-line coupled HPLC-APCI-MS and HPLC-APCI-MS/MSS. Chesnov, L. Bigler, M. Hesse, Helv. Chim. Acta 2000, 83, 3295-3305A. apertaAG 489APCI-MS/MSLink
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyaminesY. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52A. aperta / H. curtaAG 489 / Agel 489 / HO 489ReviewLink
Total synthesis of polyamine toxin HO-416b and Agel-489 using a 2-nitrobenzenesulfonamide strategyY. Hidai, T. Kan, T. Fukuyama, Chem. Pharm. Bull 2000, 48, 1570-1576Agel 489 (2)Synthesis, NMR, FAB-MS/MSLink
Total synthesis of polyamine toxin HO-416b and Agel-489 using a 2-nitrobenzenesulfonamide strategyY. Hidai, T. Kan, T. Fukuyama, Chem. Pharm. Bull 2000, 48, 1570-1576A. apertaAG 489APCI-MS/MSLink
An inhibitor of TRPV1 channels isolated from funnel web spider venomT. Kitaguchi, K. J. Swartz, Biochemistry 2005, 44, 15544-15549A. apertaAg 489Activity-studiesLink
Painful toxins acting at TRPV1B. A. Cromer, P. McIntyre, Toxicon 2008, 51, 163-173A. apertaAgatoxin 489ReviewLink
Structure-activity relationship studies of N-methylated and N-hydroxylated spider polyamine toxins as inhibitors of ionotropic glutamate receptorsN. G. Norager, M. H. Poulson, A. G. Jensen, N. S. Jeppesen, A. S. Kristensen, K. Strømgaard, J. Med. Chem. 2014, 57, 4940-4949Agel 489Synthesis, NMR, Activity-studiesLink
Low molecular mass compounds in spider venomY. M. Forster, S. Bienz, L. Bigler, 2020, in preparationdiv.Link

Spider species

Spider speciesFamilyDiscovered
Agelenopsis apertaAgelenidae1990 / V. J. Jasys
Agelenopsis potteriAgelenidae2020 / Y. M. Forster
Ariadna sp.Segestriidae2020 / Y. M. Forster
Hololena curtaAgelenidae1991 / G. B. Quistad
Hololena sp.Agelenidae2020 / Y. M. Forster

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