Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA019174
PROPERTIES
| NPAID | NPA019174 |
|---|---|
| CLUSTER ID | 6195 |
| NODE ID | 4314 |
| NAME | Hapalosin |
| FORMULA | C28H43NO6 |
| MOLECULAR WEIGHT (Da) | 489.6530 |
| ACCURATE MASS (Da) | 489.3090 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Hapalosiphon |
| ORIGIN SPECIES | welwitschii W. and G.S. West (Stigonemataceae) |
| InChIKey | NJNAHFYVTBZQHU-LFFUDGMSSA-N |
| InChI | InChI=1S/C28H43NO6/c1-6-7-8-9-13-16-24-20(4)28(33)35-26(19(2)3)27(32)29(5)22(23(30)18-25(31)34-24)17-21-14-11-10-12-15-21/h10-12,14-15,19-20,22-24,26,30H,6-9,13,16-18H2,1-5H3/t20-,22-,23+,24+,26-/m0/s1 |
| SMILES | CCCCCCC[C@@H]1[C@@H](C(=O)O[C@H](C(=O)N([C@H]([C@@H](CC(=O)O1)O)CC2=CC=CC=C2)C)C(C)C)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Stratmann; Burgoyne; Moore; Patterson; Smith Hapalosin, a cyanobacterial cyclic depsipeptide with multidrug-resistance reversing activity Journal of Organic Chemistry 1994 59 (24) 7219-7226. | ||
|---|---|---|---|
| DOI | 10.1021/jo00103a011 | PMID | - |
SYNTHESES
| CITATION 1 | Wagner B; Gonzalez GI; Tran Hun Dau ME; Zhu J Total synthesis and conformational studies of hapalosin, N-desmethylhapalosin and 8-deoxyhapalosin. Bioorganic and Medicinal Chemistry 1999 7 (5) 737-747. DOI: 10.1016/s0968-0896(98)00208-9 PMID: 10400327 | ||
|---|---|---|---|
| CITATION 2 | Palomo C; Oiarbide M; García JM; González A; Pazos R; Odriozola JM; Bañuelos P; Tello M; Linden A A practical total synthesis of hapalosin, a 12-membered cyclic depsipeptide with multidrug resistance-reversing activity, by employing improved segment coupling and macrolactonization. Journal of Organic Chemistry 2004 69 (12) 4126-4134. DOI: 10.1021/jo0497499 PMID: 15176838 | ||
| CITATION 3 | Ghosh AK; Liu W; Xu Y; Chen Z A Convergent, Enantioselective Total Synthesis of Hapalosin: A Drug with Multidrug-Resistance Reversing Activity. Angewandte Chemie International Edition 1996 35 (1) 74-76. DOI: 10.1002/anie.199600741 PMID: 30344446 | ||
