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2,4-(OH)₂-PhAcAsn5ßAla3
General Description
| Name | Value |
|---|
| Level | S-1 / C-3 |
| Discovered | 1994 / N. clavata |
| Synonym | Spidamine |
| Molecular formula | C₂₃H₃₈N₆O₆ |
| CAS | 161897-97-7 (S) / 186370-92-3 ® |
| SMILES | O=C(CC1=CC=C(O)C=C1O)NC(CC(N)=O)C(NCCCCCNC(CCNCCCN)=O)=O |
| InChI | InChI=1S/C23H38N6O6/c24-8-4-9-26-12-7-21(33)27-10-2-1-3-11-28-23(35)18(15-20(25)32)29-22(34)13-16-5-6-17(30)14-19(16)31/h5-6,14,18,26,30-31H,1-4,7-13,15,24H2,(H2,25,32)(H,27,33)(H,28,35)(H,29,34) |
| |
| Precursor 1 [M+H]⁺ | 495.29256 |
| Precursor 2 [M+2H]²⁺ | 248.14992 |
| Precursor 3 | |
| |
| HDX | 10 |
| Precursor HDX 1 [M(D₁₀)+D]⁺ | 506.36160 |
| Precursor HDX 2 [M(D₁₀)+2D]²⁺ | 254.18758 |
| 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 | 58.06513 | 41.03858 | 75.09167 |
| 2 | 350.17105 | 332.16048 | 333.14450 | 367.19760 | 129.10224 | 112.07569 | 146.12879 |
| 3 | 421.20816 | 403.19760 | 404.18161 | 438.23471 | 214.19139 | 197.16484 | 231.21794 |
| 4 | 478.26601 | 460.25545 | 461.23946 | 495.29256 | 328.23432 | 311.20777 | 345.26087 |
Additional MS/MS fragments
Recorded MS/MS spectra
| pdf | Precursor | Co-eluting | Spider | Source | Author |
|---|
| | | | | |
References
| Title | Reference | Spider | Name | Content | Link |
|---|
| Finding of primitive polyamine toxins in the venom of a Joro spider, Nephila clavata | T. Chiba, T. Akizawa, M. Matukawa, H. Pan-Hou, M. Yoshioka, Chem. Pharm. Bull 1994, 42, 1864-1869 | N. clavata | Spidamine / compound-Y | NMR (ns), Amino acid analysis | Link |
| Large-scale purification and further characterization of spidamine and joramine from venom of spider, Nephila clavata | T. Chiba, T. Akizawa, M. Matukawa, H. Pan-Hou, N. Kawai, M. Yoshieka, Chem. Pharm. Bull. 1995, 43, 2177-2181 | N. clavata | Spidamine | NMR, Activity-studies | Link |
| Total synthesis of spidamine and joramine, polyamine toxins from the Joro spider, Nephila clavata | T. Chiba, T. Akizawa, M. Matsukawa, M. Nishi, N. Kawai, M. Yoshioka, Chem. Pharm. Bull. 1996, 44, 972-979 | N. clavata | Spidamine (25) | Synthesis, NMR, Activity-studies | Link |
| Application of liquid matrix-assisted laser desorption/ionization 4-sector tandem mass spectrometry for the analysis of spider toxin acylpolyamines | T. Fujita, Y. Itagaki, M. Hisaka, T. Nakajima, M. Andriantsiferana, Rapid Commun. Mass Spectrom. 1997, 11, 1115-1119 | N. madagascariensis | Spidamine | LMALDI-CID | Link |
| Diversity of Joro spider toxins | M. Yoshioka, 1997, 117, 700-714 | | Spidamine | Review | Link |
| Syntheses and biological activities of Joro spider toxin analogs to spidamine and joramine | T. Chiba, T. Akizawa, M. Matsukawa, N. Kawai, Y. Kono, M. Yoshioka, Chem. Pharm. Bull. 1997, 45, 93-100 | | Spidamine | Activity-studies | Link |
| Acylpolyamines: Mass spectrometric analytical methods for Araneidae spider acylpolyamines | Y. Itagaki , T. Nakajima , Toxin Rev. 2000, 19, 23-52 | N. clavata | Spidamine | 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 | div. | Spidamine | LC-MS | Link |
Spider species
| Spider species | Family | Discovered |
|---|
| Nephila clavata | Araneidae | 1994 / T. Chiba |
| Trichonephila inaurata madagascariensis | Araneidae | 1997 / T. Fujita |
| Nephilingis borbonica | Araneidae | 2005 / M. S. Palma |
| Nephilingis cruentata | Araneidae | 2005 / M. S. Palma |