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4-OH-IndAc4(OH)333

General Description

Name	Value
Level	S-3 / C-1
Discovered	2020 / A. aperta
Synonym	AG 448b
Molecular formula	C₂₃H₄₀N₆O₃
CAS	389872-62-2
SMILES	`O=C(NCCCCN(O)CCCNCCCNCCCN)CC1=CNC2=C1C(O)=CC=C2`
InChI	`InChI=1S/C23H40N6O3/c24-9-4-10-25-11-5-12-26-13-6-16-29(32)15-2-1-14-27-22(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	8.23
Rt HDX	6.55

Calculated MS/MS fragments

#	a	b	c	ta	z	y	tz
1	245.12845	227.11789	228.10191	278.14992	58.06513	41.03858	75.09167
2	318.18122	300.17065	301.15467	335.20777	115.12297	98.09643	132.14952
3	375.23907	357.22850	358.21252	392.26562	172.18082	155.15428	205.20229
4	432.29692	414.28635	415.27037	449.32347	259.24924	242.22269	276.27579

Additional MS/MS fragments

m/z	Annotation
128.10699	y2’
131.11789	z2’
145.13354	z2’
146.06004	a’
174.05495	a0

Recorded MS/MS spectra

pdf	Precursor	Spider	Source	Author
Data	449.32347	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	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
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 448b	APCI-MS/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	A. aperta	AG 448b	APCI redcution artefact	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	2020 / Y. M. Forster
Agelenopsis potteri	Agelenidae	2020 / Y. M. Forster
Hololena curta	Agelenidae	2020 / Y. M. Forster
Hololena sp.	Agelenidae	2020 / Y. M. Forster

Comments

4-OH-IndAc4(OH)333 was described for A. aperta by Chesnov in 2001 (AG 448b). Eichenberger showed in 2009 that the described structure was an artifact (APCI reduction). However, 4-OH-IndAc4(OH)333 (8.23 min) awas identified in A. aperta (2019) with different retention times from 4-OH_IndAc4(OH)3(OH)33 (9.48 min).