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2,4-(OH)₂-PhAcAsn5ßAla4AlaGlyArg

General Description

Name	Value
Level	S-1 / C-3
Discovered	1990 / N. clavata
Synonym	Clavamine
Molecular formula	C₃₅H₆₀N₁₂O₉
CAS	129121-68-2
SMILES	`O=C(CC1=CC=C(O)C=C1O)NC(CC(N)=O)C(NCCCCCNC(CCNCCCCNC(C(C)NC(CNC(C(N)CCCNC(N)=N)=O)=O)=O)=O)=O`
InChI	`InChI=1S/C35H60N12O9/c1-22(46-31(53)21-45-33(55)25(36)8-7-16-44-35(38)39)32(54)42-15-6-5-12-40-17-11-29(51)41-13-3-2-4-14-43-34(56)26(20-28(37)50)47-30(52)18-23-9-10-24(48)19-27(23)49/h9-10,19,22,25-26,40,48-49H,2-8,11-18,20-21,36H2,1H3,(H2,37,50)(H,41,51)(H,42,54)(H,43,56)(H,45,55)(H,46,53)(H,47,52)(H4,38,39,44)`

Precursor 1 [M+H]⁺	793.46790
Precursor 2 [M+2H]²⁺	397.23759
Precursor 3

HDX	17
Precursor HDX 1 [M(D₁₇)+D]⁺	811.58088
Precursor HDX 2 [M(D₁₇)+2D]²⁺	406.79722
Precursor HDX 3

Rt
Rt HDX

Calculated MS/MS fragments

#	a	b	c	ta	z	y	tz
1	265.08190	247.07133	248.05535	282.10845	214.12985	197.10330	231.15640
2	350.17105	332.16048	333.14450	367.19760	285.16696	268.14042	302.19351
3	421.20816	403.19760	404.18161	438.23471	356.24046	339.21392	373.26701
4	492.28166	474.27110	475.25511	509.30821	427.27758	410.25103	444.30413
5	563.31877	545.30821	546.29223	580.34532	512.36673	495.34018	529.39328
6	620.34024	602.32967	603.31369	793.46790	626.40965	609.38311	643.43620

Additional MS/MS fragments

m/z	Annotation
123.04406	a’

Recorded MS/MS spectra

pdf	Precursor	Co-eluting	Spider	Source	Author

References

Title	Reference	Spider	Name	Content	Link
A new insecticide, clavamine, from venom of a spider, Nephila clavata - I
Purification and identification of the structure	M. Yoshioka, N. Narai, N. Kawai, M. Numata, T. Nakajima, Biog. Amines 1990, 7, 375-384	N. clavata	Clavamine	NMR, Amino acid analysis, Activity-studies	Link
Total synthesis of clavamine, insecticidually active compounds isolated from venom of Joro spider (Nephila clavata)	T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, Tetrahedron 1990, 46, 3819-3822	N. clavata	Clavamine (1)	Synthesis, NMR, Amino acid analysis, Activity-studies	Link
Characterization of a new insecticide, clavamine, from the venom of a spider, Nephila clavata by use of a synthetic compound	M. Yoshioka, N. Narai, T. Teshima, T. Matsumoto, T. Wakamiya, T. Shiba, N. Tokoro, T. Okauchi, Y. Kono, Chem.Pharm. Bull. 1992, 40, 3005-3008	N. clavata	Clavamine	Activity-studies	Link
Analysis of metal ions in spider venoms in relation to the insecticidial activity of clavamine	M. Yoshioka, N. Narai, A. Shinkai, T. Tokuda, K. Saito, M. Shioya, N. Tokoro, Y. Kono, Biol. Pharm. Bull. 1994, 17, 472-475	N. clavata	Clavamine	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	N. clavata	Clavamine	Review	Link
Diversity of Joro spider toxins	M. Yoshioka, 1997, 117, 700-714	N. clavata		Review	Link
Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines	Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52	N. clavata	Clavamine	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	N. clavata & N. borbonica	Clavamine	LC-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		Clavamine	Synthesis, NMR, Activity-studies	Link

Spider species

Spider species	Family	Discovered
Nephila clavata	Araneidae	1990 / M. Yoshioka
Nephilingis borbonica	Araneidae	2005 / M. S. Palma

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