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4-OH-IndAc3(OH)3343

General Description

NameValue
LevelS-1 / C-1
Discovered1990 / A. aperta
SynonymAG 505 / Agatoxin 505 / Agel 505 / HO 505
Molecular formulaC₂₆H₄₇N₇O₃
CAS128549-97-3
SMILESO=C(NCCCN(O)CCCNCCCNCCCCNCCCN)CC1=CNC2=C1C(O)=CC=C2
InChIInChI=1S/C26H47N7O3/c27-10-4-13-28-11-1-2-12-29-14-5-15-30-16-6-18-33(36)19-7-17-31-25(35)20-22-21-32-23-8-3-9-24(34)26(22)23/h3,8-9,21,28-30,32,34,36H,1-2,4-7,10-20,27H2,(H,31,35)
Precursor 1 [M+H]⁺506.38131
Precursor 2 [M+2H]²⁺253.69430
Precursor 3
HDX9
Precursor HDX 1 [M(D₉)+D]⁺516.44408
Precursor HDX 2 [M(D₉)+2D]²⁺259.22882
Precursor HDX 3
Rt7.08
Rt HDX5.37

Calculated MS/MS fragments

#abctazytz
1231.11280213.10224214.08626264.1342758.0651341.0385875.09167
2304.16557286.15500287.13902321.19212129.13862112.11208146.16517
3361.22342343.21285344.19687378.24997186.19647169.16993203.22302
4432.29692414.28635415.27037449.32347243.25432226.22777276.27579
5489.35477471.34420472.32822506.38131316.30709299.28054333.33364

Additional MS/MS fragments

m/zAnnotation
98.09643y2’
114.09134y2’
115.12297z2’
128.10699y2’
131.11789z2’
146.06004a’
174.05495a0
259.24924tz4-NH₃

Recorded MS/MS spectra

pdfPrecursorCo-elutingSpiderSourceAuthor
Data506.38131A. apertaFauna Laboratories Ltd., KAZY. M. Forster
Data253.69430A. apertaFauna Laboratories Ltd., KAZY. M. Forster
DataHDXA. apertaFauna Laboratories Ltd., KAZY. M. Forster
Data506.38131A. potteriFauna Laboratories Ltd., KAZY. M. Forster
Data253.69430A. potteriFauna Laboratories Ltd., KAZY. M. Forster
DataHDXA. potteriFauna Laboratories Ltd., KAZY. M. Forster
Data506.38131E. agrestisFauna Laboratories Ltd., KAZY. M. Forster
Data253.69430E. agrestisFauna Laboratories Ltd., KAZY. M. Forster
DataHDXE. agrestisFauna Laboratories Ltd., KAZY. M. Forster
Data506.38131H. curtaFauna Laboratories Ltd., KAZY. M. Forster
Data253.69430H. curtaFauna Laboratories Ltd., KAZY. M. Forster
DataHDXH. curtaFauna Laboratories Ltd., KAZY. M. Forster
Data506.38131Hololena sp.Spider Pharm, USAY. M. Forster
Data253.69430Hololena sp.Spider Pharm, USAY. M. Forster
DataHDXHololena sp.Spider Pharm, USAY. M. Forster
Data506.38131P. luctuosaFauna Laboratories Ltd., KAZY. M. Forster
DataHDXP. luctuosaFauna Laboratories Ltd., KAZY. 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 505CI (NH₃) (ns), 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 505Amino 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 505Synthesis, 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 505FAB-MS/MS, CI (NH₃) (ns), 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 505FAB-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 505Activity-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 505Activity-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 505 / Agel 505 / HO 505ReviewLink
Pharmacology of polyamine toxins from spider and waspsA. L. Mueller, R. Roeloffs, H. Jackson, The Alkaloids, Chapter 2 1995, 46, 63-94A. apertaAgel 505ReviewLink
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyaminesY. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52A. aperta & H. curtaAG 505 / Agel 505 / HO 505ReviewLink
Long-term potentiation in the presence of NMDA receptor antagonist arylalkylamine spider toxinB. C. Albensi, N. Alasti, A. L. Mueller, Journal of Neuroscience Research 2000, 62, 177-185Agel 505Activity-studiesLink
The acylpolyamines from the venom of the spider Agelenopsis apertaS. Chesnov, L. Bigler, M. Hesse, Helv. Chim. Acta 2001, 84, 2178-2197A. apertaAG 505APCI-MS/MSLink
An inhibitor of TRPV1 channels isolated from funnel web spider venomT. Kitaguchi, K. J. Swartz, Biochemistry 2005, 44, 15544-15549A. apertaAG 505Activity-studiesLink
Painful toxins acting at TRPV1B. A. Cromer, P. McIntyre, Toxicon 2008, 51, 163-173A. apertaAgatoxin 505ReviewLink
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 505Synthesis, 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
Eratigena agrestisAgelenidae2020 / Y. M. Forster
Hololena curtaAgelenidae1991 / G. B. Quistad
Hololena sp.Agelenidae2020 / Y. M. Forster
Pireneitega luctuosaAgelenidae2020 / Y. M. Forster

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