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4-OH-IndAcAsn5Lys(Me)3Arg

General Description

Name	Value
Level	S-4 / C-3
Discovered	1989 / A. lobata
Synonym	Arg 744 / Argiopinin 2
Molecular formula	C₃₅H₆₀N₁₂O₆
CAS	117233-42-8
SMILES	`O=C(CC1=CNC2=C1C(O)=CC=C2)NC(CC(N)=O)C(NCCCCCNC(C(N)CCCCN(C)CCCNC(C(N)CCCNC(N)=N)=O)=O)=O`
InChI	`InChI=1S/C35H60N12O6/c1-47(19-9-17-42-33(52)25(37)11-8-16-44-35(39)40)18-6-3-10-24(36)32(51)41-14-4-2-5-15-43-34(53)27(21-29(38)49)46-30(50)20-23-22-45-26-12-7-13-28(48)31(23)26/h7,12-13,22,24-25,27,45,48H,2-6,8-11,14-21,36-37H2,1H3,(H2,38,49)(H,41,51)(H,42,52)(H,43,53)(H,46,50)(H4,39,40,44)`

Precursor 1 [M+H]⁺	745.48315
Precursor 2 [M+2H]²⁺	373.24522
Precursor 3

HDX	16
Precursor HDX 1 [M(D₁₆)+D]⁺	762.58986
Precursor HDX 2 [M(D₁₆)+2D]²⁺	382.30171
Precursor HDX 3

Rt
Rt HDX

Calculated MS/MS fragments

#	a	b	c	ta	z	y	tz
1	288.09788	270.08732	271.07133	305.12443	214.16624	197.13969	245.20844
2	373.18703	355.17647	356.16048	390.21358	356.27685	339.25030	373.30340
3	501.28199	483.27143	484.25545	532.32419	441.36600	424.33945	458.39255
4	572.35549	554.34493	555.32894	745.48315	555.40893	538.38238	572.43548

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
Glutamate receptor anatgonists from the spider Argiope lobata venom	E. V. Grishin, T. M. Volkova, A. S. Arseniev, Biorg. Khim. 1988, 14, 883-892	A. lobata
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 2	NMR (ns), Amino acid analysis, Activity-studies	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	Argiopinine 2	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		Argiopinine 2	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	A. lobata	Arg 744 / Argiopinine 2	Review	Link
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines	Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52	A. lobata	Arg 744	Review	Link
Structure-activity relationship studies of N-methylated and N-hydroxylated spider polyamine toxins as inhibitors of ionotropic glutamate receptors	N. G. Norager, M. H. Poulson, A. G. Jensen, N. S. Jeppesen, A. S. Kristensen, K. Strømgaard, J. Med. Chem. 2014, 57, 4940-4949		Argiopinine 2	Synthesis, NMR, Activity-studies	Link

Spider species

Spider species	Family	Discovered
Argiope lobata	Araneidae	1989 / E. V. Grishin

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