Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA020899
PROPERTIES
| NPAID | NPA020899 |
|---|---|
| CLUSTER ID | 5155 |
| NODE ID | 3692 |
| NAME | Zincophorin |
| FORMULA | C33H60O7 |
| MOLECULAR WEIGHT (Da) | 568.8360 |
| ACCURATE MASS (Da) | 568.4339 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | griseus |
| InChIKey | XMCIULDTDFJACK-FXLACHKASA-N |
| InChI | InChI=1S/C33H60O7/c1-10-13-19(2)18-22(5)29(35)20(3)14-11-12-15-27(34)23(6)30(36)25(8)31(37)26(9)32-21(4)16-17-28(40-32)24(7)33(38)39/h11,14,18-21,23-32,34-37H,10,12-13,15-17H2,1-9H3,(H,38,39)/b14-11+,22-18+/t19-,20-,21+,23+,24+,25+,26+,27-,28+,29-,30+,31+,32+/m1/s1 |
| SMILES | CCC[C@@H](C)/C=C(\C)/[C@@H]([C@H](C)/C=C/CC[C@H]([C@H](C)[C@@H]([C@H](C)[C@@H]([C@H](C)[C@@H]1[C@H](CC[C@H](O1)[C@H](C)C(=O)O)C)O)O)O)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Brooks HA; Gardner D; Poyser JP; King TJ THE STRUCTURE AND ABSOLUTE STEREOCHEMISTRY OF ZINCOPHORIN (ANTIBIOTIC M144255): A MONOBASIC CARBOXYLIC ACID IONOPHORE HAVING A REMARKABLE SPECIFICITY FOR DIVALENT CATIONS Journal of Antibiotics 1984 37 (11) 1501-1504. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.37.1501 | PMID | 6549004 |
SYNTHESES
| CITATION 1 | Defosseux M; Blanchard N; Meyer C; Cossy J Total synthesis of zincophorin and its methyl ester. Journal of Organic Chemistry 2004 69 (14) 4626-47. DOI: 10.1021/jo0496042 PMID: 15230584 | ||
|---|---|---|---|
| CITATION 2 | Komatsu K; Tanino K; Miyashita M Stereoselective total synthesis of the ionophore antibiotic zincophorin. Angewandte Chemie International Edition 2004 43 (33) 4341-5. DOI: 10.1002/anie.200460434 PMID: 15368388 | ||
| CITATION 3 | Song Z; Hsung RP A formal total synthesis of (+)-zincophorin. Observation of an unusual urea-directed Stork-Crabtree hydrogenation. Organic Letters 2007 9 (11) 2199-202. DOI: 10.1021/ol070791a PMID: 17480091 | ||
