Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA012504
PROPERTIES
| NPAID | NPA012504 |
|---|---|
| CLUSTER ID | 2190 |
| NODE ID | 1743 |
| NAME | Leupyrrin A1 |
| FORMULA | C41H58N2O10 |
| MOLECULAR WEIGHT (Da) | 738.9190 |
| ACCURATE MASS (Da) | 738.4091 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Sorangium |
| ORIGIN SPECIES | cellulosum So ce705 |
| InChIKey | KPUUXWUEEITCMH-DBMCUXRASA-N |
| InChI | InChI=1S/C41H58N2O10/c1-23(2)16-27-18-35(45)52-37-36(53-40(47)41(37,7)22-44)26(6)11-12-28-13-14-31(42-28)38-43-32(34(51-38)21-50-39(27)46)19-29-30(25(5)10-9-15-48-8)20-49-33(29)17-24(3)4/h11,13-14,19,23-24,27,32-34,36-37,42,44H,9-10,12,15-18,20-22H2,1-8H3/b26-11+,29-19-,30-25+/t27-,32+,33-,34+,36-,37-,41+/m0/s1 |
| SMILES | COCCC/C(C)=C1\CO[C@@H](CC(C)C)\C1=C/[C@H]1N=C2O[C@@H]1COC(=O)[C@@H](CC(C)C)CC(=O)O[C@H]1[C@@H](OC(=O)[C@]1(C)CO)/C(C)=C/CC1=CC=C2N1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Bjoern Bode, Helge; Irschik, Herbert; Wenzel, Silke C.; Reichenbach, Hans; Mueller, Rolf; Hoefle, Gerhard The leupyrrins: A structurally unique family of secondary metabolites from the myxobacterium Sorangium cellulosum Journal of Natural Products 2003 66 (9) 1203-1206. | ||
|---|---|---|---|
| DOI | 10.1021/np030109v | PMID | 14510597 |
SYNTHESES
| CITATION 1 | Herkommer D; Thiede S; Wosniok PR; Dreisigacker S; Tian M; Debnar T; Irschik H; Menche D Stereochemical determination of the leupyrrins and total synthesis of leupyrrin A1. Journal of the American Chemical Society 2015 137 (12) 4086-4089. DOI: 10.1021/jacs.5b01894 PMID: 25769018 | ||
|---|---|---|---|
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C/C/1=C\CC2=CC=C(N2)C3=NC(C(O3)COC(=O)[C@H](CC(=O)OC4C1OC(=O)C4(C)CO)CC(C)C)/C=C/5\C(OC\C5=C(\C)/CCCOC)CC(C)C | Bjoern Bode, Helge; Irschik, Herbert; Wenzel, Silke C.; Reichenbach, Hans; Mueller, Rolf; Hoefle, Gerhard The leupyrrins: A structurally unique family of secondary metabolites from the myxobacterium Sorangium cellulosum Journal of Natural Products 2003 66 (9) 1203-1206. DOI: 10.1021/np030109v PMID: 14510597 | ||
| 2 | COCCC/C(C)=C1\CO[C@@H](CC(C)C)\C1=C/[C@H]1N=C2O[C@@H]1COC(=O)[C@@H](CC(C)C)CC(=O)O[C@H]1[C@@H](OC(=O)[C@]1(C)CO)/C(C)=C/CC1=CC=C2N1 | Herkommer D; Thiede S; Wosniok PR; Dreisigacker S; Tian M; Debnar T; Irschik H; Menche D Stereochemical determination of the leupyrrins and total synthesis of leupyrrin A1. Journal of the American Chemical Society 2015 137 (12) 4086-4089. DOI: 10.1021/jacs.5b01894 PMID: 25769018 | ||
