Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA016325
PROPERTIES
| NPAID | NPA016325 |
|---|---|
| CLUSTER ID | 1125 |
| NODE ID | 961 |
| NAME | Lagunamide A |
| FORMULA | C45H71N5O10 |
| MOLECULAR WEIGHT (Da) | 842.0880 |
| ACCURATE MASS (Da) | 841.5201 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Lyngbya |
| ORIGIN SPECIES | majuscula |
| InChIKey | VOJKUGWTQYFABB-ZJXVFMLESA-N |
| InChI | InChI=1S/C45H71N5O10/c1-14-26(4)37-43(56)49(12)32(10)45(58)59-38(27(5)15-2)30(8)35(51)23-22-29(7)44(57)60-39(28(6)16-3)40(53)46-31(9)41(54)50(13)34(24-33-20-18-17-19-21-33)42(55)48(11)25-36(52)47-37/h17-22,26-28,30-32,34-35,37-39,51H,14-16,23-25H2,1-13H3,(H,46,53)(H,47,52)/b29-22+/t26-,27+,28+,30+,31+,32+,34-,35+,37+,38+,39-/m1/s1 |
| SMILES | CC[C@H](C)[C@H]1[C@H]([C@H](C/C=C(/C(=O)O[C@@H](C(=O)N[C@H](C(=O)N([C@@H](C(=O)N(CC(=O)N[C@H](C(=O)N([C@H](C(=O)O1)C)C)[C@H](C)CC)C)CC2=CC=CC=C2)C)C)[C@@H](C)CC)\C)O)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Tripathi, Ashootosh; Puddick, Jonathan; Prinsep, Michele R.; Rottmann, Matthias; Tan, Lik Tong Lagunamides A and B: Cytotoxic and antimalarial cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula Journal of Natural Products 2010 73 (11) 1810-1814. | ||
|---|---|---|---|
| DOI | 10.1021/np100442x | PMID | 20936843 |
SYNTHESES
| CITATION 1 | Gorges J; Kazmaier U Matteson Homologation-Based Total Synthesis of Lagunamide A. Organic Letters 2018 20 (7) 2033-2036. DOI: 10.1021/acs.orglett.8b00576 PMID: 29578725 | ||
|---|---|---|---|
| CITATION 2 | Dai L; Chen B; Lei H; Wang Z; Liu Y; Xu Z; Ye T Total synthesis and stereochemical revision of lagunamide A. Chemical Communications 2012 48 (69) 8697-8699. DOI: 10.1039/c2cc34187e PMID: 22824869 | ||
| CITATION 3 | Huang W; Ren RG; Dong HQ; Wei BG; Lin GQ Diverse synthesis of marine cyclic depsipeptide lagunamide A and its analogues. Journal of Organic Chemistry 2013 78 (21) 10747-10762. DOI: 10.1021/jo401687s PMID: 24090274 | ||
