Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA019914
PROPERTIES
| NPAID | NPA019914 |
|---|---|
| CLUSTER ID | 58 |
| NODE ID | 54 |
| NAME | Geldanamycin |
| FORMULA | C29H40N2O9 |
| MOLECULAR WEIGHT (Da) | 560.6440 |
| ACCURATE MASS (Da) | 560.2734 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | hygroscopicus var. enhygrus var. nova |
| InChIKey | QTQAWLPCGQOSGP-KSRBKZBZSA-N |
| InChI | InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/m1/s1 |
| SMILES | COC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(/C)C(=O)NC(=CC1=O)C2=O |
ORIGINAL ISOLATION REFERENCE
| CITATION | DeBoer, C; Meulman, PA; Wnuk, RJ; Peterson, DH Geldanamycin, a new antibiotic Journal of Antibiotics 1970 23 (9) 442-447. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.23.442 | PMID | 5459626 |
SYNTHESES
| CITATION 1 | Andrus MB; Meredith EL; Simmons BL; Soma Sekhar BB; Hicken EJ Total synthesis of (+)-geldanamycin and (-)-o-quinogeldanamycin with use of asymmetric anti- and syn-glycolate aldol reactions. Organic Letters 2002 4 (20) 3549-3552. DOI: 10.1021/ol0267432 PMID: 12323066 | ||
|---|---|---|---|
| CITATION 2 | Qin HL; Panek JS Total synthesis of the Hsp90 inhibitor geldanamycin. Organic Letters 2008 10 (12) 2477-2479. DOI: 10.1021/ol800749w PMID: 18489177 | ||
| CITATION 3 | Andrus MB; Meredith EL; Hicken EJ; Simmons BL; Glancey RR; Ma W Total synthesis of (+)-geldanamycin and (-)-o-quinogeldanamycin: asymmetric glycolate aldol reactions and biological evaluation. Journal of Organic Chemistry 2003 68 (21) 8162-8169. DOI: 10.1021/jo034870l PMID: 14535799 | ||
