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4-OH-IndAcAsn533Arg

General Description

Name	Value
Level	S-1 / C-3
Discovered	1987 / A. aurantia
Synonym	AR 659 / Arg 659 / Argiopinin 3 / Argiotoxin 659 / ArgTX 659
Molecular formula	C₃₁H₅₃N₁₁O₅
CAS	111944-83-3
SMILES	`O=C(NC(CC(N)=O)C(NCCCCCNCCCNCCCNC(C(N)CCCNC(N)=N)=O)=O)CC1=CNC2=C1C(O)=CC=C2`
InChI	`InChI=1S/C31H53N11O5/c32-22(8-5-16-40-31(34)35)29(46)38-17-7-14-37-13-6-12-36-11-2-1-3-15-39-30(47)24(19-26(33)44)42-27(45)18-21-20-41-23-9-4-10-25(43)28(21)23/h4,9-10,20,22,24,36-37,41,43H,1-3,5-8,11-19,32H2,(H2,33,44)(H,38,46)(H,39,47)(H,42,45)(H4,34,35,40)`

Precursor 1 [M+H]⁺	660.43039
Precursor 2 [M+2H]²⁺	330.71883
Precursor 3

HDX	15
Precursor HDX 1 [M(D₁₅)+D]⁺	676.53082
Precursor HDX 2 [M(D₁₅)+2D]²⁺	339.27219
Precursor HDX 3

Rt
Rt HDX

Calculated MS/MS fragments

#	a	b	c	ta	z	y	tz
1	288.09843	270.08787	271.07188	305.12498	214.16679	197.14024	231.19334
2	373.18758	355.17702	356.16103	390.21413	271.22464	254.19809	288.25119
3	430.24543	412.23487	413.21888	447.27198	356.31379	339.28724	373.34034
4	487.30328	469.29272	470.27673	660.43094	470.35672	453.33017	487.38327

Additional MS/MS fragments

m/z	Annotation
146.06004	a’
174.05495	a0

Recorded MS/MS spectra

pdf	Precursor	Co-eluting	Spider	Source	Author

References

Title	Reference	Spider	Name	Content	Link
Structures and biological activities of three synaptic antagonists from orb weaver spider venom	M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, V. J Venema, Biochem. Biophys. Res. Com. 1987, 148, 678-683	A. aurantia	AR 659	Synthesis, NMR (ns), Amino acid analysis, Activity-studies	Link
Isolation and characterisation of glutamate receptor antagonists from venoms of orb-web spiders	T. Budd, P. Clinton, A. Dell, I. R. Duce, S. J. Johnson, D. L. J. Quicke, G. W. Taylor, P. N. R. Usherwood, G. Usoh, Brain Res. 1988, 448, 30-39	A. florida & A. trifasciata	Arg 659	NMR, Amino acid analysis, Activity-studies	Link
The total synthesis of argiotoxins 636, 659 and 673	V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, R. A. Volkmann, Tetrahedron Letters 1988, 29, 6223-6226		Arg 659	Synthesis, NMR	Link
Isolation and structure analysis of components from venom of the spider Argiope lobata	E. V. Grishin, T. M. Volkova, A. S. Arseniev, Toxicon 1989, 27, 541-549	A. lobata	Argiopinin 3	NMR, 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		AR 659	UV Reference for 4-OH-IndAc head	Link
Argiopine, argiopinines, and pseudoargiopinines as glutamate receptor blockers in hippocampal neurons	N. I. Kiskin, O. A. Kryshtal, A. Y. Tsyndrenko, T. M. Volkova, E. V. Grishin, Neurophysiology 1990, 21, 525-532	A. lobata	argiopinin 3	Activity-studies	Link
Arylamine spider toxins antagonize NMDA receptor-mediated synaptic transmission in rat hippocampal slices	A. L. Mueller, B. C. Albensi, A. H. Ganong, L. S. Reynolds, H. Jackson, Synapse 1991, 9, 244-250		Argiotoxin 659	Activity-studies	Link
Polyamine spider toxins are potent un-competitive antagonists of rat cortex excitatory amino acid receptors	M. S. Davies, M. P. Baganoff, E. V. Grishin, T. H. Lanthorn, T. M. Volkova, G. B. Watson, R. C. Wiegand, Eur J Pharmacol. 1992, 227, 51-56	A. lobata	Argiopinin 3	Activity-studies	Link
Antropod toxins as leads for novel insecticides: An assessment of polyamine amides as glutamate antagonists	I. 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, 303-322		ArgTX 659	Review	Link
Interaction of bovine brain glycoprotein with glutamate and argiopinins	T. M. Volkova, N. A. Avetisyan, T. G. Galkina, A. B. Kudelin, E. V. Grishin, Chemistry of Peptides and Proteins 1993, ⁵⁄₆, 741-749
Polyamine toxins from spiders and wasps	A. Schäfer, H. Benz, W. Fiedler, A. Guggisberg, S. Bienz, M. Hesse, The Alkaloids 1994, 45, 1-125	div.	AR 659 / Arg 659 / Argiopinine 3 / Argiotoxin 659	Review	Link
Polyamine und Polyamin-Derivate in der Natur	H. Geneste, M. Hesse, Chem. unserer Zeit 1998, 32, 206-218	Argiop sp.	Arg 659	Review	Link
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines	Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52	A. lobata	Arg 659	Review	Link

Spider species

Spider species	Family	Discovered
Argiope aurantia	Araneidae	1987 / M. E. Adams
Argiope florida	Araneidae	1988 / T. Budd
Argiope lobata	Araneidae	1989 / E. V. Grishin
Argiope trifasciata	Araneidae	1988 / T. Budd

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