Compounds
| ID | Spectrum Quality | Annotated Name |
|---|---|---|
| CCMSLIB00000577767 | Gold | 3 |
WARNING - This compound is excluded from the NP Atlas. The information displayed is for reference only.
Reason: Structure flagged during revision as not known
Citation: Sable, Ganesh A.; Park, Jaekwan; Kim, Hyunsik; Lim, Soo‐Jeong; Jang, Soonmin; Lim, Dongyeol Solid‐Phase Total Synthesis of the Proposed Structure of Coibamide A and Its Derivative: Highly Methylated Cyclic Depsipeptides. European Journal of Organic Chemistry 2015 2015 (32) 7043-7052. DOI: 10.1002/ejoc.201500697
COMPOUND NPA008310
PROPERTIES
| NPAID | NPA008310 |
|---|---|
| CLUSTER ID | None |
| NODE ID | None |
| NAME | Coibamide A |
| FORMULA | C65H110N10O16 |
| MOLECULAR WEIGHT (Da) | 1287.6490 |
| ACCURATE MASS (Da) | 1286.8101 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Leptolyngbya |
| ORIGIN SPECIES | sp. |
| InChIKey | LVHKHLZPRPTQJG-ADLPPTMNSA-N |
| InChI | InChI=1S/C65H110N10O16/c1-26-40(10)52-56(77)66-41(11)57(78)70(17)47(31-36(2)3)55(76)67-46(33-44-27-29-45(89-25)30-28-44)58(79)69(16)42(12)64(85)90-43(13)53(62(83)72(19)50(35-88-24)61(82)74(52)21)75(22)59(80)48(32-37(4)5)71(18)60(81)49(34-87-23)73(20)63(84)54(39(8)9)91-65(86)51(38(6)7)68(14)15/h27-30,36-43,46-54H,26,31-35H2,1-25H3,(H,66,77)(H,67,76)/t40-,41-,42-,43+,46-,47-,48-,49-,50-,51-,52-,53-,54+/m0/s1 |
| SMILES | CC[C@H](C)[C@H]1C(=O)N[C@@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CC=C(OC)C=C2)C(=O)N(C)[C@@H](C)C(=O)O[C@H](C)[C@H](N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](COC)N(C)C(=O)[C@H](OC(=O)[C@H](C(C)C)N(C)C)C(C)C)C(=O)N(C)[C@@H](COC)C(=O)N1C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Medina, Rebecca A.; Goeger, Douglas E.; Hills, Patrice; Mooberry, Susan L.; Huang, Nelson; Romero, Luz I.; Ortega-Barria, Eduardo; Gerwick, William H.; McPhail, Kerry L. Coibamide A, a potent antiproliferative cyclic depsipeptide from the panamanian marine cyanobacterium Leptolyngbya sp Journal of the American Chemical Society 2008 130 (20) 6324-6325. | ||
|---|---|---|---|
| DOI | 10.1021/ja801383f | PMID | 18444611 |
SYNTHESES
| CITATION 1 | Yao G; Pan Z; Wu C; Wang W; Fang L; Su W Efficient Synthesis and Stereochemical Revision of Coibamide A. Journal of the American Chemical Society 2015 137 (42) 13488-13491. DOI: 10.1021/jacs.5b09286 PMID: 26469305 | ||
|---|---|---|---|
| CITATION 2 | Yao G; Wang W; Ao L; Cheng Z; Wu C; Pan Z; Liu K; Li H; Su W; Fang L Improved Total Synthesis and Biological Evaluation of Coibamide A Analogues. Journal of Medicinal Chemistry 2018 61 (19) 8908-8916. DOI: 10.1021/acs.jmedchem.8b01141 PMID: 30247036 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)O[C@@H]([C@@H](C(=O)N([C@H](C(=O)N1C)COC)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](COC)N(C)C(=O)[C@H](C(C)C)OC(=O)[C@H](C(C)C)N(C)C)C)C)C)CC2=CC=C(C=C2)OC)CC(C)C)C)C | Medina, Rebecca A.; Goeger, Douglas E.; Hills, Patrice; Mooberry, Susan L.; Huang, Nelson; Romero, Luz I.; Ortega-Barria, Eduardo; Gerwick, William H.; McPhail, Kerry L. Coibamide A, a potent antiproliferative cyclic depsipeptide from the panamanian marine cyanobacterium Leptolyngbya sp Journal of the American Chemical Society 2008 130 (20) 6324-6325. DOI: 10.1021/ja801383f PMID: 18444611 | ||
| 2 | CC[C@H](C)[C@H]1C(=O)N[C@@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CC=C(OC)C=C2)C(=O)N(C)[C@@H](C)C(=O)O[C@H](C)[C@H](N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](COC)N(C)C(=O)[C@H](OC(=O)[C@H](C(C)C)N(C)C)C(C)C)C(=O)N(C)[C@@H](COC)C(=O)N1C | Yao G; Pan Z; Wu C; Wang W; Fang L; Su W Efficient Synthesis and Stereochemical Revision of Coibamide A. Journal of the American Chemical Society 2015 137 (42) 13488-13491. DOI: 10.1021/jacs.5b09286 PMID: 26469305 | ||
