Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA021433
PROPERTIES
| NPAID | NPA021433 |
|---|---|
| CLUSTER ID | 903 |
| NODE ID | 782 |
| NAME | Papulacandin D |
| FORMULA | C31H42O10 |
| MOLECULAR WEIGHT (Da) | 574.6670 |
| ACCURATE MASS (Da) | 574.2778 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Papularia |
| ORIGIN SPECIES | sphaerosperma |
| InChIKey | XKSZJTQIZHUMGA-HJHUFFDJSA-N |
| InChI | InChI=1S/C31H42O10/c1-4-19(2)11-7-5-8-12-20(3)23(34)13-9-6-10-14-26(36)40-29-28(37)25(17-32)41-31(30(29)38)27-21(18-39-31)15-22(33)16-24(27)35/h5-6,8-10,12,14-16,19,23,25,28-30,32-35,37-38H,4,7,11,13,17-18H2,1-3H3/b8-5+,9-6+,14-10+,20-12-/t19-,23+,25+,28+,29-,30+,31-/m0/s1 |
| SMILES | CC[C@H](C)CC/C=C/C=C(/C)[C@H](O)C/C=C/C=C/C(=O)O[C@H]1[C@H](O)[C@@H](CO)O[C@]2(OCC3=C2C(O)=CC(O)=C3)[C@@H]1O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Traxler P; Gruner J; Auden JA Papulacandins, a new family of antibiotics with antifungal activity, I. Fermentation, isolation, chemical and biological characterization of papulacandins A, B, C, D and E. Journal of Antibiotics 1977 30 (4) 289-296. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.30.289 | PMID | 324958 |
SYNTHESES
| CITATION 1 | Denmark SE; Regens CS; Kobayashi T Total synthesis of papulacandin D. Journal of the American Chemical Society 2007 129 (10) 2774-6. DOI: 10.1021/ja070071z PMID: 17305346 | ||
|---|---|---|---|
| CITATION 2 | Denmark SE; Kobayashi T; Regens CS Total Synthesis of (+)-Papulacandin D. Tetrahedron 2010 66 (26) 4745-4759. DOI: 10.1016/j.tet.2010.03.093 PMID: 20711516 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC[C@H](C)CC/C=C\C=C(\C)/[C@@H](C/C=C/C=C/C(=O)O[C@H]1[C@@H]([C@H](O[C@]2([C@H]1O)C3=C(C=C(C=C3CO2)O)O)CO)O)O | Traxler P; Gruner J; Auden JA Papulacandins, a new family of antibiotics with antifungal activity, I. Fermentation, isolation, chemical and biological characterization of papulacandins A, B, C, D and E. Journal of Antibiotics 1977 30 (4) 289-296. DOI: 10.7164/antibiotics.30.289 PMID: 324958 | ||
| 2 | CC[C@H](C)CC/C=C/C=C(/C)[C@H](O)C/C=C/C=C/C(=O)O[C@H]1[C@H](O)[C@@H](CO)O[C@]2(OCC3=C2C(O)=CC(O)=C3)[C@@H]1O | Barrett, Anthony G. M.; Peña, Michael; Willardsen, J. Adam Total Synthesis and Structural Elucidation of the Antifungal Agent Papulacandin D. Journal of Organic Chemistry 1996 61 (3) 1082-1100. DOI: 10.1021/jo951895e | ||
