| Stereochemistry | EPIMERIC |
| Molecular Formula | C58H91N13O20 |
| Molecular Weight | 1290.4205 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 12 / 13 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]1(CCCN1C(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)C\C=C\CCCCCC(C)CC)C(C)C(O)=O)[C@H](C)N)C(C)C)C(=O)N[C@@H](C)[C@]2([H])NC(=O)[C@@]3([H])CCCCN3C2=O
InChI
InChIKey=XBNDESPXQUOOBQ-LSMLZNGOSA-N
InChI=1S/C58H91N13O20/c1-8-30(4)18-13-11-9-10-12-14-21-39(72)63-36(26-44(79)80)51(83)68-46(31(5)58(90)91)54(86)65-35(25-43(77)78)50(82)60-27-40(73)64-34(24-42(75)76)49(81)61-28-41(74)66-47(32(6)59)55(87)67-45(29(2)3)56(88)71-23-17-20-38(71)52(84)62-33(7)48-57(89)70-22-16-15-19-37(70)53(85)69-48/h12,14,29-38,45-48H,8-11,13,15-28,59H2,1-7H3,(H,60,82)(H,61,81)(H,62,84)(H,63,72)(H,64,73)(H,65,86)(H,66,74)(H,67,87)(H,68,83)(H,69,85)(H,75,76)(H,77,78)(H,79,80)(H,90,91)/b14-12+/t30?,31-,32+,33+,34+,35+,36+,37-,38+,45+,46+,47-,48+/m1/s1
| Molecular Formula | C58H91N13O20 |
| Molecular Weight | 1290.4205 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | EPIMERIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 12 / 13 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
Amphomycin is a natural antibacterial lipopeptide initially reported by researchers at Bristol-Myers in 1953 from Streptomyces canus. Lipopeptides are cyclic depsipeptides with a peptidyl side chain capped with a saturated alkyl tail. They preferentially target Gram-positive bacteria and may be useful against drug resistant strains. Amphomycin is closely related to a number of "lost" antibiotics, such as aspartocin, crystallomycin, glumamycin, friulimicin, laspartocin, tsushimycin and zaomycin. Interest in amphomycin was re-awakened with the discovery of friulimicin activity against antibiotic resistant strains. Whole cell analysis by solid-state NMR indicates that in vivo mode of action for amphomycin is complex. While the downstream effect of purine biosynthesis inhibition by amphomycin is unknown, presumably it would directly alter the overall metabolism of bacteria.
