Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA004614
PROPERTIES
| NPAID | NPA004614 |
|---|---|
| CLUSTER ID | 249 |
| NODE ID | 228 |
| NAME | Sphingofungin F |
| FORMULA | C21H39NO6 |
| MOLECULAR WEIGHT (Da) | 401.5440 |
| ACCURATE MASS (Da) | 401.2777 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Paecilomyces |
| ORIGIN SPECIES | variotii |
| InChIKey | KEACSJIKRANUJC-NZBAJYJFSA-N |
| InChI | InChI=1S/C21H39NO6/c1-3-4-5-10-13-16(23)14-11-8-6-7-9-12-15-17(24)18(25)19(26)21(2,22)20(27)28/h12,15,17-19,24-26H,3-11,13-14,22H2,1-2H3,(H,27,28)/b15-12+/t17-,18+,19-,21-/m0/s1 |
| SMILES | CCCCCCC(=O)CCCCCC/C=C/[C@H](O)[C@@H](O)[C@H](O)[C@](C)(N)C(=O)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Horn, W S; Smith, J L; Bills, G F; Raghoobar, S L; Helms, G L; Kurtz, M B; Marrinan, J A; Frommer, B R; Thornton, R A; Mandala, S M Sphingofungins E and F: novel serinepalmitoyl transferase inhibitors from Paecilomyces variotii. Journal of Antibiotics 1992 45 (10) 1692-1696. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.45.1692 | PMID | 1474000 |
SYNTHESES
| CITATION 1 | Lee KY; Oh CY; Ham WH Total synthesis of sphingofungin F. Organic Letters 2002 4 (25) 4403-5. DOI: 10.1021/ol020164f PMID: 12465898 | ||
|---|---|---|---|
| CITATION 2 | Gan FF; Yang SB; Luo YC; Yang WB; Xu PF Total synthesis of sphingofungin F based on chiral tricyclic iminolactone. Journal of Organic Chemistry 2010 75 (8) 2737-40. DOI: 10.1021/jo100183d PMID: 20329736 | ||
| CITATION 3 | Tsuzaki S; Usui S; Oishi H; Yasushima D; Fukuyasu T; Oishi T; Sato T; Chida N Total synthesis of sphingofungin F by orthoamide-type overman rearrangement of an unsaturated ester. Organic Letters 2015 17 (7) 1704-7. DOI: 10.1021/acs.orglett.5b00475 PMID: 25769012 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CCCCCCC(=O)CCCCCC/C=C/C(C(C(C(C)(C(=O)O)N)O)O)O | Horn, W S; Smith, J L; Bills, G F; Raghoobar, S L; Helms, G L; Kurtz, M B; Marrinan, J A; Frommer, B R; Thornton, R A; Mandala, S M Sphingofungins E and F: novel serinepalmitoyl transferase inhibitors from Paecilomyces variotii. Journal of Antibiotics 1992 45 (10) 1692-1696. DOI: 10.7164/antibiotics.45.1692 PMID: 1474000 | ||
| 2 | CCCCCCC(=O)CCCCCC/C=C/[C@H](O)[C@@H](O)[C@H](O)[C@](C)(N)C(=O)O | Tsuzaki S; Usui S; Oishi H; Yasushima D; Fukuyasu T; Oishi T; Sato T; Chida N Total synthesis of sphingofungin F by orthoamide-type overman rearrangement of an unsaturated ester. Organic Letters 2015 17 (7) 1704-7. DOI: 10.1021/acs.orglett.5b00475 PMID: 25769012 | ||
