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2,4-(OH)₂-PhAcAsn433

General Description

Name	Value
Level	S-1 / C-1
Discovered	1997 / N. borbonica
Synonym	NPTX 466 / NPTX 466B / LF 466E
Molecular formula	C₂₂H₃₈N₆O₅
CAS	133698-34-7
SMILES	`O=C(CC1=CC=C(O)C=C1O)NC(CC(N)=O)C(NCCCCNCCCNCCCN)=O`
InChI	`InChI=1S/C22H38N6O5/c23-7-3-9-26-11-4-10-25-8-1-2-12-27-22(33)18(15-20(24)31)28-21(32)13-16-5-6-17(29)14-19(16)30/h5-6,14,18,25-26,29-30H,1-4,7-13,15,23H2,(H2,24,31)(H,27,33)(H,28,32)`

Precursor 1 [M+H]⁺	467.29764
Precursor 2 [M+2H]²⁺	234.15246
Precursor 3

HDX	10
Precursor HDX 1 [M(D₁₀)+D]⁺	478.36669
Precursor HDX 2 [M(D₁₀)+2D]²⁺	240.19012
Precursor HDX 3

Rt	3.29
Rt HDX	2.59

Calculated MS/MS fragments

#	a	b	c	ta	z	y	tz
1	265.08190	247.07133	248.05535	282.10845	58.06513	41.03858	75.09167
2	336.15540	318.14483	319.12885	353.18195	115.12297	98.09643	132.14952
3	393.21325	375.20268	376.18670	410.23980	186.19647	169.16993	203.22302
4	450.27110	432.26053	433.24455	467.29764	300.23940	283.21285	317.26595

Additional MS/MS fragments

m/z	Annotation
123.04406	a’

Recorded MS/MS spectra

pdf	Precursor	Co-eluting	Spider	Source	Author
Data	467.29764		L. cornutus	Spider Pharm, USA	Y. M. Forster
Data	234.15246		L. cornutus	Spider Pharm, USA	Y. M. Forster
Data	HDX		L. cornutus	Spider Pharm, USA	Y. M. Forster
Data	467.29764		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
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	NPTX 466	FAB-MS/MS (ns)	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 (ns)	Link
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines	Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52	N. borbonica & N. cruentata	NPTX 466B	Review	Link
Study on the structure activity relationships of NPTX-594, a spider toxin belonging to the type-B acylpolyamine structure	T. Wakamiya, T. Kinoshita, Y. Hattori, Y. Yamaguchi, H. Naoki, G. Corzo, T. Nakajima, Bull. Chem. Soc. Jpn. 2004, 77, 331-340		NPTX 466 (2)	Synthesis, NMR, 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 466B	LC-MS	Link
Development of a high-resolution MS-based method for the structural elucidation of polyamine spider toxins	S. Eichenberger, PhD-Thesis, University of Zurich 2009, 1-156	L. patagiatus	LF 466E	nLC-ESI-MS/MS, Amino acid analysis	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
Larinioides cornutus	Araneidae	2020 / Y. M. Forster
Larinioides patagiatus	Araneidae	2009 / S. Eichenberger
Nephila clavata	Araneidae	2005 / M. S. Palma
Trichonephila clavipes	Araneidae	2020 / Y. M. Forster
Trichonephila inaurata madagascariensis	Araneidae	2005 / M. S. Palma
Nephilingis borbonica	Araneidae	1997 / Y. Itagaki
Nephilingis cruentata	Araneidae	1997 / M. S. Palma

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