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4-OH-IndAcAsn5ßAla43

General Description

Name	Value
Level	S-1 / C-2
Discovered	1996 / N. clavata
Synonym	Nephilatoxin 1 / NPTX 1
Molecular formula	C₂₉H₄₈N₈O₅
CAS	119688-54-9 (S)
SMILES	`O=C(CC1=CNC2=C1C(O)=CC=C2)NC(CC(N)=O)C(NCCCCCNC(CCNCCCCNCCCN)=O)=O`
InChI	`InChI=1S/C29H48N8O5/c30-11-7-14-32-12-4-5-13-33-17-10-26(40)34-15-2-1-3-16-35-29(42)23(19-25(31)39)37-27(41)18-21-20-36-22-8-6-9-24(38)28(21)22/h6,8-9,20,23,32-33,36,38H,1-5,7,10-19,30H2,(H2,31,39)(H,34,40)(H,35,42)(H,37,41)`

Precursor 1 [M+H]⁺	589.38204
Precursor 2 [M+2H]²⁺	295.19466
Precursor 3

HDX	11
Precursor HDX 1 [M(D₁₁)+D]⁺	601.45736
Precursor HDX 2 [M(D₁₁)+2D]²⁺	301.73546
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	58.06513	41.03858	75.09167
2	373.18703	355.17647	356.16048	390.21358	129.13862	112.11208	146.16517
3	444.22415	426.21358	427.19760	461.25069	200.17574	183.14919	217.20229
4	515.29764	497.28708	498.27110	532.32419	285.26489	268.23834	302.29144
5	572.35549	554.34493	555.32894	589.38204	399.30782	382.28127	416.33436

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
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 1 / NPTX 1	Amino acid analysis, Activity-studies, 6-OH-IndAc…	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 1	Review	Link
Facile Synthesis of 6-Hydroxyindole-3-acetic acid: on the structure of aromatic subunit of nephilatoxin 1-6	T. Shinada, M. Miyachi, Y. Itagaki, H. Naoki, K. Yoshihara, T. Nakajima, Tetrahedron Lett. 1996, 37, 7099-7102	N. clavata	NPTX 1	partial synthesis, NMR	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 1 / NPTX 1	CID	Link
Total synthesis of Nephilatoxin-1 (NPTX-1), a Joro spider (Nephila clavata) toxin having a 4-hydroxyindole nucleus	M. Miyashita, H. Saito, M. Matsushita, M. Miyazawa, Y. Itagaki, T. Nakajima, Tetrahedron Lett. 1997, 38, 8297-8298	N. clavata	NPTX 1	Synthesis, NMR	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
Structures of spider toxins: Hydroxyindole-3-acetylpolyamines and a new generalized structure of type-E compounds obtained from the venom of the Joro spider, Nephila clavata	M. Hisada, T. Fujita, H. Naoki, Y. Itagaki, H. Irie, M. Miyashita, T. Nakajima, Toxicon 1998, 36, 1115-1125	N. clavata	NPTX 1	CID (ns)	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 1	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 1	Review	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 1	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 1 (3)	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 1	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 1 (2)	Synthesis of analogues, Activity-studies	Link

Spider species

Spider species	Family	Discovered
Nephila clavata	Araneidae	1996 / T. Shinada
Nephilingis borbonica	Araneidae	1997 / Y. Itagaki
Nephilingis cruentata	Araneidae	1997 / M. S. Palma

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