☰
Navigation :

2,4-(OH)₂-PhAcAsn5ßAla4Arg

General Description

NameValue
LevelS-1 / C-1
Discovered1986 / N. pilipes
SynonymNSTX 3
Molecular formulaC₃₀H₅₂N₁₀O₇
CAS1190024-26-9
SMILESO=C(CC1=CC=C(O)C=C1O)NC(CC(N)=O)C(NCCCCCNC(CCNCCCCNC(C(N)CCCNC(N)=N)=O)=O)=O
InChIInChI=1S/C30H52N10O7/c31-22(7-6-15-39-30(33)34)28(46)37-14-5-4-11-35-16-10-26(44)36-12-2-1-3-13-38-29(47)23(19-25(32)43)40-27(45)17-20-8-9-21(41)18-24(20)42/h8-9,18,22-23,35,41-42H,1-7,10-17,19,31H2,(H2,32,43)(H,36,44)(H,37,46)(H,38,47)(H,40,45)(H4,33,34,39)
Precursor 1 [M+H]⁺665.40932
Precursor 2 [M+2H]²⁺333.20830
Precursor 3
HDX15
Precursor HDX 1 [M(D₁₅)+D]⁺681.50975
Precursor HDX 2 [M(D₁₅)+2D]²⁺341.76165
Precursor HDX 3
Rt7.75
Rt HDX6.59

Calculated MS/MS fragments

#abctazytz
1265.08190247.07133248.05535282.10845228.18189211.15534245.20844
2350.17105332.16048333.14450367.19760299.21900282.19245316.24555
3421.20816403.19760404.18161438.23471384.30815367.28160401.33470
4492.28166474.27110475.25511665.40932498.35108481.32453515.37763

Additional MS/MS fragments

m/zAnnotation
123.04406a’

Recorded MS/MS spectra

pdfPrecursorCo-elutingSpiderSourceAuthor
Data665.40932T. clavipesSpider Pharm, USAY. M. Forster
Data333.20830T. clavipesSpider Pharm, USAY. M. Forster
DataHDXT. clavipesSpider Pharm, USAY. M. Forster

References

TitleReferenceSpiderNameContentLink
Chemical characterization of spider toxin, JSTX and NSTXY. Aramaki, T. Yasuhara, T. Higashijima, M. Yoshioka, A. Miwa, N. Kawai, T. Nakajima, Proc. Jpn. Acad. 1986, 62, 359-362N. pilipesNSTX 3NMR, Amino acid analysisLink
Chemical characterization of spider toxin, NSTXY. Aramaki, T. Yasuhara, T. Higashijima, A. Miwa, N. Kawai, T. Nakajima, Biomed. Res. 1987, 8, 167N. pilipesNSTX 3NMR, Amino acid analysis, Activity-studiesLink
Synthesis of a new neurotoxin NSTX-3 of Papua New Guinean spiderT. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, T. Shiba, Tetrahedron Letters 1987, 28, 3509-3510N. pilipesNSTX 3Synthesis, NMRLink
Synthesis of neurotoxic Nephila spider venoms: NSTX-3 and JSTX-3D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Philips, N. A. Saccomano, R. A. Volkmann, Tetrahedron Letters 1989, 30, 2337-2340NSTX 3Synthesis, NMRLink
Characterization of binding sites for spider toxin, [3H]NSTX-3, in the rat brainH. Ino, S. Nakade, M. Niinobe, K. Ikenaka, T. Teshima, T. Wakamiya, T. Matsumoto, T. Shiba, N. Kawai, K. Mikoshiba, Neuroscience Research 1990, 8, 29-39NSTX 3Activity-studiesLink
Spider toxins , NSTX and JSTX block synaptic transmission in insect CNSB. Hue, T. Piek, Comparative Biochemistry and Physiology, Part C: Pharmacology, Toxicology & Endocrinology 1990, 95C, 229-232NSTX 3Activity-studiesLink
Structure-activity relationship of NSTX-3, spider toxin of Nephila maculataT. Teshima, T. Matsumoto, T. Wakamiya, T. Shiba, T. Nakajima, N. Kawai, Tetrahedron 1990, 46, 3813-3818NSTX 3Activity-studiesLink
Comparison of some arthropod toxins and toxin fragments as antagonists of excitatory amino acid-induced excitation of rat spinal neuronsM. G. Jones, D. Lodge, European Journal of Pharmacology 1991, 204, 203-209NSTX 3Activity-studiesLink
Total synthesis of NSTX-3, spider toxin of Nephila maculataT. Teshima, T. Matsumoto, T. Wakamiya, T. Shiba, Y. Aramaki, T. Nakajima, N. Kawai, Tetrahedron 1991, 47, 3305-3312NSTX 3 (1)Synthesis, NMR (ns),Link
Antropod toxins as leads for novel insecticides: An assessment of polyamine amides as glutamate antagonistsI. S. Blagbrough, P. T. H. Brackley, M. Bruce, B. W. Bycroft, A. J. Mather, S. Millington, H. L. Sudan, P. N. R. Usherwood, Toxicon 1992, 30, 303-322NSTX 3ReviewLink
Polyamine toxins from spiders and waspsA. Schäfer, H. Benz, W. Fiedler, A. Guggisberg, S. Bienz, M. Hesse, The Alkaloids 1994, 45, 1-125N. pilipesNSTX 3ReviewLink
Practical, convergent total synthesis of polyamine amide spider toxin NSTX-3I. S. Blagbrough, E. Moya, S. P. Walford, Tetrahedron Letters 1996, 37, 551-554NSTX 3 (1)SynthesisLink
Diversity of Joro spider toxinsM. Yoshioka, 1997, 117, 700-714N. pilipesNSTX 3ReviewLink
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyaminesY. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52N. pilipesNSTX 3ReviewLink
Novel mechanism of blocking axonal Na+ channels by three macrocyclic polyamine analogues and two spider toxinsM. Yakehiro, Y. Furukawa, T. Koike, E. Kimura, T. Nakajima, K. Yamaoka, I. Seyama, British Journal of Pharmacology 2001, 132, 63-72NSTX 3Activity-studiesLink
An efficient and versatile synthesis of acylpolyamine spider toxinsK. Nihei, M. J. Kato, T. Yamane, M. S. Palma, K. Konno, Bioorg. Med. Chem. Lett. 2002, 12, 299-302NSTX 3SynthesisLink
A natural combinatorial chemistry strategy in acylpolyamine toxins from Nephilinae orb-web spidersM. S. Palma, T. Nakajima, Toxin Rev. 2005, 24, 209-234N. borbonica & N. clavataNSTX 3LC-MSLink
Spider polyamine toxinN. Kawai, Toxicon Review 2005, 24, 273-289NSTX 3ReviewLink
An efficient and versatile synthesis of all structural types of acylpolyamine spider toxinsK. Nihei, M. J. Kato, T. Yamane, K. Konno, Tetrahedron 2006, 62, 8335-8350NSTX 3 (6)Synthesis, NMR, ESI-MS/MSLink
General synthesis of beta-alanine-containing spider polyamine toxins and discovery of Nephila polyamine toxins 1 and 8 as highly potent inhibitors of ionotropic glutamate receptorsS. Lucas, M. H. Poulsen, N. G. Norager, A. F. Barslund, T. B. Bach, A. S. Kristensen, K. Strømgaard, J. Med. Chem. 2012, 55, 10297-10301NSTX 3Synthesis, NMR, Activity-studiesLink
Low molecular mass compounds in spider venomY. M. Forster, S. Bienz, L. Bigler, 2020, in preparationdiv.Link

Spider species

Spider speciesFamilyDiscovered
Nephila clavataAraneidae2005 / M. S. Palma
Trichonephila clavipesAraneidae2020 / Y. M. Forster
Nephila pilipesAraneidae1986 / Y. Aramaki
Nephilingis borbonicaAraneidae2005 / M. S. Palma

Comments