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IndAcAsn5ßAla43

General Description

Name	Value
Level	S-1 / C-2
Discovered	1988 / N. clavata
Synonym	Nephilatoxin 8 / NPTX 8
Molecular formula	C₂₉H₄₈N₈O₄
CAS	—
SMILES	`O=C(CC1=CNC2=C1C=CC=C2)NC(CC(N)=O)C(NCCCCCNC(CCNCCCCNCCCN)=O)=O`
InChI	`InChI=1S/C29H48N8O4/c30-12-8-15-32-13-6-7-14-33-18-11-27(39)34-16-4-1-5-17-35-29(41)25(20-26(31)38)37-28(40)19-22-21-36-24-10-3-2-9-23(22)24/h2-3,9-10,21,25,32-33,36H,1,4-8,11-20,30H2,(H2,31,38)(H,34,39)(H,35,41)(H,37,40)`

Precursor 1 [M+H]⁺	573.38713
Precursor 2 [M+2H]²⁺	287.19720
Precursor 3

HDX	10
Precursor HDX 1 [M(D₁₀)+D]⁺	584.45617
Precursor HDX 2 [M(D₁₀)+2D]²⁺	293.23486
Precursor HDX 3

Rt
Rt HDX

Calculated MS/MS fragments

#	a	b	c	ta	z	y	tz
1	272.10297	254.09240	255.07642	289.12952	58.06513	41.03858	75.09167
2	357.19212	339.18155	340.16557	374.21867	129.13862	112.11208	146.16517
3	428.22923	410.21867	411.20268	445.25578	200.17574	183.14919	217.20229
4	499.30273	481.29217	482.27618	516.32928	285.26489	268.23834	302.29144
5	556.36058	538.35001	539.33403	573.38713	399.30782	382.28127	416.33436

Additional MS/MS fragments

m/z	Annotation
130.06513	a’
158.06004	a0

Recorded MS/MS spectra

pdf	Precursor	Co-eluting	Spider	Source	Author

References

Title	Reference	Spider	Name	Content	Link
Isolation and chemical characterization of a series of new spider toxin (nephilatoxins) in the venom of Joro spider, Nephila clavata	T. Toki, T. Yasuhara, Y. Aramaki, K. Osawa, A. Miwa, N. Kawai, T. Nakajima, Biomed. Res. 1988, 9, 421-428	N. clavata	Nephilatoxin 8 / NPTX 8	Amino acid analysis, Activity-studies	Link
A new type of spider toxin, nephilatoxin, in the venom of the Joro spider, Nephila clavata	T. Toki, T. Yasuhara, Y. Aramaki, N. Kawai, T. Nakajima, Biomed. Res. 1988, 9, 75-79	N. clavata	Nephilatoxin 8	Amino acid analysis, Activity-studies	Link
Total synthesis of Nephilatoxin-8 (NPTX-8), a new neurotoxin of Joro spider (Nephila clavata)	M. Miyashita, M. Matsushita, H. Sato, T. Toki, T. Nakajima, H. Irie, Chemistry Letters 1993, 6, 929-932	N. clavata	Nephilatoxin 8 / NPTX 8	Synthesis	Link
Polyamine toxins from spiders and wasps	A. Schäfer, H. Benz, W. Fiedler, A. Guggisberg, S. Bienz, M. Hesse, The Alkaloids 1994, 45, 1-125	N. clavata	NPTX 8	Review	Link
Synthetic studies on nephilatoxins, new neurotoxins of Joro spider (Nephila clavata)	M. Miyashita, Yuki Gosei Kagaku Kyokaishi 1996, 54, 846-858	N. clavata	NPTX 8	Review	Link
Detection of new spider toxins from a Nephilengys borbonica venom gland using on-line µ-column HPLC continuous flow (FRIT) FAB LC/MS and MS/MS	Y. Itagaki, T. Fujita, H. Naoki, T. Yasuhara, M. Andriantsiferana, T. Nakajima, Nat. Toxins 1997, 5, 1-13	N. borbonica	Nephilatoxin 8 / NPTX 8	CID	Link
Mass spectrometric structure determination of spider toxins: Arginine-containing acylpolyamines from venoms of Brazilian garden spider Nephilengys cruentata	M. S. Palma, Y. Itagaki, T. Fujita, M. Hisada, H. Naoki, T. Nakajima, Nat. Toxins 1997, 5, 47-57	N. cruentata		MS/MS	Link
Structural characterization of a new acylpolyaminetoxin from the venom of Brazilian garden spider Nephilenys cruentata	M. S. Palma, Y. Itagaki, T. Fujita, H. Naoki, T. Nakajima, Toxicon 1998, 36, 485-493	N. cruentata	NPTX 8	Frit-FAB-MS	Link
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines	Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52	div.	NPTX 8	Review	Link
Synthesis and paralytic activities of squaryl amino acid-containing polyamine toxins	T. Shinada, Y. Nakagawa, K. Hayashi, G. Corzo, T. Nakajima, Y. Ohfune, Amino Acids 2003, 24, 293-301		NPTX 8	Activity-studies	Link
A natural combinatorial chemistry strategy in acylpolyamine toxins from Nephilinae orb-web spiders	M. S. Palma, T. Nakajima, Toxin Rev. 2005, 24, 209-234	div.	NPTX 8	LC-MS	Link
An efficient and versatile synthesis of all structural types of acylpolyamine spider toxins	K. Nihei, M. J. Kato, T. Yamane, K. Konno, Tetrahedron 2006, 62, 8335-8350		NPTX 8 (2)	Synthesis, NMR, ESI-MS/MS	Link
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 receptors	S. Lucas, M. H. Poulsen, N. G. Norager, A. F. Barslund, T. B. Bach, A. S. Kristensen, K. Strømgaard, J. Med. Chem. 2012, 55, 10297-10301		NPTX 8	Synthesis, NMR, Activity-studies	Link
Structure-activity relationship study of spider polyamine toxins as inhibitor of ionotropic glutamate receptors	X.-F. Xiong, M. H. Poulsen, R. A. Hussein, N. G. Norager, K. Strømgaard, ChemMedChem 2014, 9, 2661-2670		NPTX 8 (3)	Synthesis of analogues, Activity-studies	Link

Spider species

Spider species	Family	Discovered
Nephila clavata	Araneidae	1988 / T. Toki
Trichonephila inaurata madagascariensis	Araneidae	2005 / M. S. Palma
Nephilingis borbonica	Araneidae	1997 / Y. Itagaki
Nephilingis cruentata	Araneidae	1998 / M. S. Palma

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