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4-OH-IndAc3(OH)343

General Description

Name	Value
Level	S-1 / C-1
Discovered	1990 / A. aperta
Synonym	AG 448 / Agel 448 / HO 448
Molecular formula	C₂₃H₄₀N₆O₃
CAS	128550-00-5
SMILES	`O=C(NCCCN(O)CCCNCCCCNCCCN)CC1=CNC2=C1C(O)=CC=C2`
InChI	`InChI=1S/C23H40N6O3/c24-9-4-12-25-10-1-2-11-26-13-5-15-29(32)16-6-14-27-22(31)17-19-18-28-20-7-3-8-21(30)23(19)20/h3,7-8,18,25-26,28,30,32H,1-2,4-6,9-17,24H2,(H,27,31)`

Precursor 1 [M+H]⁺	449.32347
Precursor 2 [M+2H]²⁺	225.16537
Precursor 3

HDX	8
Precursor HDX 1 [M(D₈)+D]⁺	458.37996
Precursor HDX 2 [M(D₈)+2D]²⁺	230.19675
Precursor HDX 3

Rt	6.96
Rt HDX	5.29

Calculated MS/MS fragments

#	a	b	c	ta	z	y	tz
1	231.11280	213.10224	214.08626	264.13427	58.06513	41.03858	75.09167
2	304.16557	286.15500	287.13902	321.19212	129.13862	112.11208	146.16517
3	375.23907	357.22850	358.21252	392.26562	186.19647	169.16993	219.21794
4	432.29692	414.28635	415.27037	449.32347	259.24924	242.22269	276.27579

Additional MS/MS fragments

m/z	Annotation
98.09643	y2’
115.12297	z2’
146.06004	a’
174.05495	a0

Recorded MS/MS spectra

pdf	Precursor	Co-eluting	Spider	Source	Author
Data	449.32347		A. aperta	Fauna Laboratories Ltd., KAZ	Y. M. Forster
Data	2225.16537		A. aperta	Fauna Laboratories Ltd., KAZ	Y. M. Forster
Data	HDX		A. aperta	Fauna Laboratories Ltd., KAZ	Y. M. Forster
Data	449.32347		A. potteri	Fauna Laboratories Ltd., KAZ	Y. M. Forster
Data	225.16537		A. potteri	Fauna Laboratories Ltd., KAZ	Y. M. Forster
Data	HDX		A. potteri	Fauna Laboratories Ltd., KAZ	Y. M. Forster
Data	449.32347		H. curta	Fauna Laboratories Ltd., KAZ	Y. M. Forster
Data	225.16537		H. curta	Fauna Laboratories Ltd., KAZ	Y. M. Forster
Data	HDX		H. curta	Fauna Laboratories Ltd., KAZ	Y. M. Forster
Data	449.32347		Hololena sp.	Spider Pharm, USA	Y. M. Forster
Data	225.16537		Hololena sp.	Spider Pharm, USA	Y. M. Forster
Data	HDX		Hololena sp.	Spider Pharm, USA	Y. M. Forster

References

Title	Reference	Spider	Name	Content	Link
Isolation, structure elucidation, and synthesis of novel hydroxylamine-containing polyamines from the venom of the Agelenopsis aperta spider	V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, R. A. Volkman, JACS 1990, 112, 6696-6704	A. aperta	AG 448	Synthesis, NMR, Amino acid analysis	Link
Arylamine toxins from funnel-web spider (Agelenopsis aperta) venom antagonize N-methyl-D-aspartate receptor function in mammalian brain	T. N. Parks, A. L. Mueller, L. D. Artman, B. C. Albensi, E. F. Nemeth, H. Jackson, V. J. Jasys, N. A. Saccomano, R. A. Volkmann, J. Biol. Chem. 1991, 266, 21523-21529	A. aperta	AG 448	Activity-studies	Link
Paralytic and insecticidal toxins from the funnel web spider, Hololena curta	G. B. Quistad, C. C. Reuter, W. S. Skinner, P. A. Dennis, S. Suwanrumpha, E. W. Fu, Toxicon 1991, 29, 329-336	H. curta	HO 448	FAB-MS/MS (ns), Activity-studies	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	A. aperta & H. curta	AG 448 / Agel 448 / HO 448	Review	Link
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines	Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52	A. aperta & H. curta	AG 448 / Agel 448 / HO 448	Review	Link
The acylpolyamines from the venom of the spider Agelenopsis aperta	S. Chesnov, L. Bigler, M. Hesse, Helv. Chim. Acta 2001, 84, 2178-2197	A. aperta	AG 448	APCI-MS/MS	Link
Detection and characterization of natural polyamines by high-performance liquid chromatography-atmospheric pressure chemical ionization (electrospray ionization) mass spectroscopy	S. Chesnov, L. Bigler, M. Hesse, Eur. J. Mass Spectrom. 2002, 8, 1-16	A. aperta	AG 448	Review	Link
Polyamine alkaloids	S. Bienz, P. Bisegger, A. Guggisberg, M. Hesse, Nat. Prod. Rep. 2005, 22, 647-658	A. aperta	AG 448	Review	Link
Efficient and flexible solid-phase synthesis of N-hydroxypolyamine derivatives	M. Meret, S. Bienz, Eur. J. Org. Chem. 2008, 33, 5518-5525		Agel 448	Synthesis	Link
Decomposition of N-hydroxylated compounds during atmospheric pressure chemical ionization	S. Eichenberger, M. Méret, S. Bienz, L. Bigler, J. Mass. Spectrom. 2010, 45, 190-197	A. aperta	(9)	LC-APCI-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
Agelenopsis aperta	Agelenidae	1990 / V. J. Jasys
Agelenopsis potteri	Agelenidae	2020 / Y. M. Forster
Hololena curta	Agelenidae	1991 / G. B. Quistad
Hololena sp.	Agelenidae	2020 / Y. M. Forster

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