HuagongsheHuagongshe Chemistry Print Report · For research reference only
Amphomycin
amfamycin · Nsc267431 · Amphomycin
Identifiers & Physical Properties
| CAS No. | 1402-82-0 |
|---|---|
| Molecular formula | C58H91N13O20 |
| Average molar mass | 1,290.437 g/mol |
| Monoisotopic mass | 1,289.65033231 g/mol |
| SMILES | CCC(C)CCCCC/C=C/CC(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)NCC(=O)N[C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)[C@@H]1NC(=O)[C@H]2CCCCN2C1=O)C(C)C)[C@H](C)N)[C@@H](C)C(=O)O |
| InChIKey | XBNDESPXQUOOBQ-LSMLZNGOSA-N |
| PubChem CID | 91663250 |
| ChEMBL | CHEMBL2103921 |
| EC No. | 215-760-0 |
| DTXSID | DTXSID101017657 |
Chemical & Physical Properties
| alpha | D25 +7.5° (c = 1 at pH 6) |
|---|---|
| Boiling point | 854.06°C (rough estimate) |
| Density | 1.0985 (rough estimate) |
| Refractive index | 1.6700 (estimate) |
| Storage conditions | Store at -20°C |
| Solubility | Soluble in DMSO |
| Physical state | solid |
| Color | Crystals |
| EWG's Food Scores | 1 |
| FDA UNII | 4P63B997RT |
| Toxicity | LD50 orl-mus: 500 mg/kg 85GDA2 4(1),317,80 |
Safety & Regulations
| Toxicity | LD50 orl-mus: 500 mg/kg 85GDA2 4(1),317,80 |
|---|
Applications & Uses
Uses
Amphomycin is a lipopeptide antibiotic produced by Streptomycetes and Actinoplanes, initially reported by researchers at Bristol-Myers in 1953 from Streptomyces canus. Amphomycin was marketed as a complex of closely related analogues in the 1950s and 1960s. Structure elucidation was not completed until 2000. Amphomycin is active against Gram positive bacteria, inhibiting peptidoglycan synthesis and blocking cell wall development. Amphomycin is closely related to a number of “lost” antibiotics, aspartocin, crystallomycin, glumamycin, friulimicin, laspartocin, tsushimycin and zaomycin. Interest in amphomycin was re-awakened with the discovery of friulimicin activity against antibiotic resistant strains.