Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA010377
PROPERTIES
| NPAID | NPA010377 |
|---|---|
| CLUSTER ID | 107 |
| NODE ID | 102 |
| NAME | Syringolin A |
| FORMULA | C24H39N5O6 |
| MOLECULAR WEIGHT (Da) | 493.6050 |
| ACCURATE MASS (Da) | 493.2900 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Pseudomonas |
| ORIGIN SPECIES | syringaepv.syringae |
| InChIKey | RUWSLQOIGKYPEZ-YPXRAQKDSA-N |
| InChI | InChI=1S/C24H39N5O6/c1-13(2)16-10-11-18(30)25-12-8-7-9-17(21(31)26-16)27-22(32)19(14(3)4)28-24(35)29-20(15(5)6)23(33)34/h7,9-11,13-17,19-20H,8,12H2,1-6H3,(H,25,30)(H,26,31)(H,27,32)(H,33,34)(H2,28,29,35)/b9-7+,11-10+/t16-,17+,19+,20+/m1/s1 |
| SMILES | CC(C)[C@H](NC(=O)N[C@H](C(=O)N[C@H]1/C=C/CCNC(=O)/C=C/[C@H](C(C)C)NC1=O)C(C)C)C(=O)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Wäspi, Urs; Blanc, Daniel; Winkler, Tammo; Rüedi, Peter; Dudler, Robert Syringolin, a Novel Peptide Elicitor from Pseudomonas syringaepv.syringae that Induces Resistance toPyricularia oryzaein Rice Molecular Plant-Microbe Interactions 1998 11 (8) 727-733. | ||
|---|---|---|---|
| DOI | 10.1094/mpmi.1998.11.8.727 | PMID | - |
SYNTHESES
| CITATION 1 | Pirrung MC; Biswas G; Ibarra-Rivera TR Total synthesis of syringolin A and B. Organic Letters 2010 12 (10) 2402-5. DOI: 10.1021/ol100761z PMID: 20426399 | ||
|---|---|---|---|
| CITATION 2 | Dai C; Stephenson CR Total synthesis of syringolin A. Organic Letters 2010 12 (15) 3453-5. DOI: 10.1021/ol101252y PMID: 20597471 | ||
| CITATION 3 | Chiba T; Hosono H; Nakagawa K; Asaka M; Takeda H; Matsuda A; Ichikawa S Total synthesis of syringolin A and improvement of its biological activity. Angewandte Chemie International Edition 2014 53 (19) 4836-9. DOI: 10.1002/anie.201402428 PMID: 24668894 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC(C)C1/C=C\C(=O)NCC/C=C\C(C(=O)N1)NC(=O)C(C(C)C)NC(=O)NC(C(C)C)C(=O)O | Wäspi, Urs; Blanc, Daniel; Winkler, Tammo; Rüedi, Peter; Dudler, Robert Syringolin, a Novel Peptide Elicitor from Pseudomonas syringaepv.syringae that Induces Resistance toPyricularia oryzaein Rice Molecular Plant-Microbe Interactions 1998 11 (8) 727-733. DOI: 10.1094/mpmi.1998.11.8.727 | ||
| 2 | CC(C)[C@H](NC(=O)N[C@H](C(=O)N[C@H]1/C=C/CCNC(=O)/C=C/[C@H](C(C)C)NC1=O)C(C)C)C(=O)O | Shimizu T; Satoh T; Murakoshi K; Sodeoka M Asymmetric total synthesis of (-)-spirofungin A and (+)-spirofungin B. Organic Letters 2005 7 (25) 5573-5576. DOI: 10.1021/ol052039k PMID: 16320994 | ||
