Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA003067
PROPERTIES
| NPAID | NPA003067 |
|---|---|
| CLUSTER ID | 1746 |
| NODE ID | 1417 |
| NAME | Stereocalpin A |
| FORMULA | C29H36N2O5 |
| MOLECULAR WEIGHT (Da) | 492.6160 |
| ACCURATE MASS (Da) | 492.2624 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Stereocaulon |
| ORIGIN SPECIES | alpinum |
| InChIKey | PKKZNSZCFXCHRE-VLNNBNGDSA-N |
| InChI | InChI=1S/C29H36N2O5/c1-5-12-25-19(2)26(32)20(3)27(33)30-23(17-21-13-8-6-9-14-21)28(34)31(4)24(29(35)36-25)18-22-15-10-7-11-16-22/h6-11,13-16,19-20,23-25H,5,12,17-18H2,1-4H3,(H,30,33)/t19-,20+,23-,24-,25+/m0/s1 |
| SMILES | CCC[C@H]1OC(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](C)C(=O)[C@H]1C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Seo, Changon; Yim, Joung Han; Lee, Hong Kum; Park, Seong Min; Sohn, Jae-Hak; Oh, Hyuncheol Stereocalpin A, a bioactive cyclic depsipeptide from the Antarctic lichen Stereocaulon alpinum Tetrahedron Letters 2008 49 (1) 29-31. | ||
|---|---|---|---|
| DOI | 10.1016/j.tetlet.2007.11.022 | PMID | - |
SYNTHESES
| CITATION 1 | Kaneda M; Inuki S; Ohno H; Oishi S Total Synthesis and Stereochemical Revision of Stereocalpin A: Mirror-Image Approach for Stereochemical Assignments of the Peptide-Polyketide Macrocycle. Journal of Organic Chemistry 2018 83 (6) 3047-3060. DOI: 10.1021/acs.joc.8b00118 PMID: 29470088 | ||
|---|---|---|---|
| CITATION 2 | Ghosh AK; Xu CX A convergent synthesis of the proposed structure of antitumor depsipeptide stereocalpin A. Organic Letters 2009 11 (9) 1963-1966. DOI: 10.1021/ol900412u PMID: 19354233 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CCC[C@H]1[C@@H](C(=O)[C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)O1)CC2=CC=CC=C2)C)CC3=CC=CC=C3)C)C | Seo, Changon; Yim, Joung Han; Lee, Hong Kum; Park, Seong Min; Sohn, Jae-Hak; Oh, Hyuncheol Stereocalpin A, a bioactive cyclic depsipeptide from the Antarctic lichen Stereocaulon alpinum Tetrahedron Letters 2008 49 (1) 29-31. DOI: 10.1016/j.tetlet.2007.11.022 | ||
| 2 | CCC[C@H]1OC(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](C)C(=O)[C@H]1C | Kaneda M; Inuki S; Ohno H; Oishi S Total Synthesis and Stereochemical Revision of Stereocalpin A: Mirror-Image Approach for Stereochemical Assignments of the Peptide-Polyketide Macrocycle. Journal of Organic Chemistry 2018 83 (6) 3047-3060. DOI: 10.1021/acs.joc.8b00118 PMID: 29470088 | ||
