4-OH-IndAcOrnAsn5ßAla4ßAla4
General Description
| Name | Value |
|---|---|
| Level | S-4 / C-3 |
| Discovered | 1996 / N. clavata |
| Synonym | Nephilatoxin 3 / NPTX 3 |
| Molecular formula | C₃₈H₆₅N₁₁O₇ |
| CAS | — |
| SMILES | O=C(CC1=CNC2=C1C(O)=CC=C2)NC(C(CCCN)NC(CC(N)=O)C(NCCCCCNC(CCNCCCCNC(CCNCCCCN)=O)=O)=O)=O |
| InChI | InChI=1S/C38H65N11O7/c39-15-2-5-17-42-22-13-34(53)45-20-7-6-18-43-23-14-33(52)44-19-3-1-4-21-46-37(55)30(25-32(41)51)48-29(11-9-16-40)38(56)49-35(54)24-27-26-47-28-10-8-12-31(50)36(27)28/h8,10,12,26,29-30,42-43,47-48,50H,1-7,9,11,13-25,39-40H2,(H2,41,51)(H,44,52)(H,45,53)(H,46,55)(H,49,54,56) |
| Precursor 1 [M+H]⁺ | 788.51412 |
| Precursor 2 [M+2H]²⁺ | 394.76070 |
| Precursor 3 | |
| HDX | 15 |
| Precursor HDX 1 [M(D₁₅)+D]⁺ | 804.61455 |
| Precursor HDX 2 [M(D₁₅)+2D]²⁺ | 403.31405 |
| Precursor HDX 3 | |
| Rt | |
| Rt HDX |
Calculated MS/MS fragments
| # | a | b | c | ta | z | y | tz |
|---|---|---|---|---|---|---|---|
| 1 | 288.13427 | 270.12370 | 271.10772 | 305.16082 | 72.08078 | 55.05423 | 89.10732 |
| 2 | 402.17720 | 384.16663 | 385.15065 | 419.20374 | 143.11789 | 126.09134 | 160.14444 |
| 3 | 487.26634 | 469.25578 | 470.23980 | 504.29289 | 214.19139 | 197.16484 | 231.21794 |
| 4 | 558.30346 | 540.29289 | 541.27691 | 575.33001 | 285.22850 | 268.20195 | 302.25505 |
| 5 | 629.37696 | 611.36639 | 612.35041 | 646.40351 | 370.31765 | 353.29110 | 387.34420 |
| 6 | 700.41407 | 682.40351 | 683.38752 | 717.44062 | 484.36058 | 467.33403 | 501.38713 |
| 7 | 771.48757 | 753.47701 | 754.46102 | 788.51412 | 598.43989 | 581.41334 | 615.46644 |
Additional MS/MS fragments
| m/z | Annotation |
|---|---|
| 146.06004 | a’ |
| 174.05495 | a0 |
Recorded MS/MS spectra
| Precursor | Co-eluting | Spider | Source | Author | |
|---|---|---|---|---|---|
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 3 / NPTX 3 | 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 3 | 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 3 | partial synthesis, NMR | Link |
| Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines | Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52 | N. clavata | NPTX 3 | 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 | NPTX 3 | LC-MS | Link |
Spider species
| Spider species | Family | Discovered |
|---|---|---|
| Nephila clavata | Araneidae | 1996 / T. Shinada |