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4-OH-IndAcAsn5ßAla4ßAla4ßAla4ßAla4

General Description

Name	Value
Level	S-1 / C-1
Discovered	1996 / N. clavata
Synonym	Nephilatoxin 6 / NPTX 6 / NPTX 957
Molecular formula	C₄₇H₈₃N₁₃O₈
CAS	119613-52-4 (S)
SMILES	`O=C(CC1=CNC2=C1C(O)=CC=C2)NC(CC(N)=O)C(NCCCCCNC(CCNCCCCNC(CCNCCCCNC(CCNCCCCNC(CCNCCCCN)=O)=O)=O)=O)=O`
InChI	`InChI=1S/C47H83N13O8/c48-19-2-5-20-50-29-15-42(64)55-25-9-7-22-52-31-17-44(66)57-27-11-8-23-53-32-18-43(65)56-26-10-6-21-51-30-16-41(63)54-24-3-1-4-28-58-47(68)38(34-40(49)62)60-45(67)33-36-35-59-37-13-12-14-39(61)46(36)37/h12-14,35,38,50-53,59,61H,1-11,15-34,48H2,(H2,49,62)(H,54,63)(H,55,64)(H,56,65)(H,57,66)(H,58,68)(H,60,67)`

Precursor 1 [M+H]⁺	958.65603
Precursor 2 [M+2H]²⁺	479.83165
Precursor 3

HDX	16
Precursor HDX 1 [M(D₁₆)+D]⁺	975.76274
Precursor HDX 2 [M(D₁₆)+2D]²⁺	488.88815
Precursor HDX 3

Rt	10.83
Rt HDX	9.54

Calculated MS/MS fragments

#	a	b	c	ta	z	y	tz
1	288.09788	270.08732	271.07133	305.12443	72.08078	55.05423	89.10732
2	373.18703	355.17647	356.16048	390.21358	143.11789	126.09134	160.14444
3	444.22415	426.21358	427.19760	461.25069	214.19139	197.16484	231.21794
4	515.29764	497.28708	498.27110	532.32419	285.22850	268.20195	302.25505
5	586.33476	568.32419	569.30821	603.36131	356.30200	339.27545	373.32855
6	657.40826	639.39769	640.38171	674.43481	427.33912	410.31257	444.36566
7	728.44537	710.43481	711.41882	745.47192	498.41261	481.38607	515.43916
8	799.51887	781.50831	782.49232	816.54542	569.44973	552.42318	586.47628
9	870.55598	852.54542	853.52944	887.58253	654.53888	637.51233	671.56543
10	941.62948	923.61892	924.60293	958.65603	768.58181	751.55526	785.60835

Additional MS/MS fragments

m/z	Annotation
146.06004	a’
174.05495	a0

Recorded MS/MS spectra

pdf	Precursor	Co-eluting	Spider	Source	Author
Data	958.65603		T. clavipes	Spider Pharm, USA	Y. M. Forster
Data	479.83165		T. clavipes	Spider Pharm, USA	Y. M. Forster
Data	HDX		T. clavipes	Spider Pharm, USA	Y. M. Forster

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 6 / NPTX 6	Amino acid analysis, Activity-studies, wrong structure	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 6	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 6	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 6 / NPTX 957	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
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 6 / NPTX 957	NMR, CID	Link
Total synthesis of NPTX-5 and NPTX-6, Joro spider (Nephila clavata) toxins having a unique putreanine trimer and putreanine tetramer acylpolyamine chain	H. Saito, E. Yuri, M. Miyazawa, Y. Itagaki, T. Nakajima, M. Miyashita, Tetrahedron Letters 1998, 39, 6479-6482	N. clavata	NPTX 6 (2)	Synthesis	Link
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines	Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52	div.	NPTX 6	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 6	LC-MS	Link
Low molecular mass compounds in spider venom	Y. M. Forster, S. Bienz, L. Bigler, 2020, in preparation	div.			Link

Spider species

Spider species	Family	Discovered
Nephila clavata	Araneidae	1996 / T. Shinada
Trichonephila clavipes	Araneidae	2020 / Y. M. Forster
Nephilingis borbonica	Araneidae	1997 / Y. Itagaki
Nephilingis cruentata	Araneidae	1997 / M. S. Palma

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