Amphomycin

Synonym(s): Glumamycin  |  Ampfomycin

Class: Lipopeptide

Spectrum of activity:	Gram-positive
Details of activity:	Active against Staphylococcus aureus; interferes with cell-wall synthesis by inhibiting transfer of the peptidoglycan precursor moiety (MurNAc-pentapeptide) to the membrane lipid carrier, undecaprenyl phosphate/ interacts with lipid carrier C55-P in calcium-dependent manner (MraY inhibitor)
Description:	Natural product from Streptomyces zaomyceticus No. 7548
Year first mentioned:	1953
Development status:	Experimental

Chemical structure(s):
Canonical SMILES:	CCC(C)CCCCC/C=C/CC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H]([C@@H](C)C(=O)O)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@H](C)N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)[C@H]2C(=O)N3CCCC[C@@H]3C(=O)N2
Isomeric SMILES:	CCC(C)CCCCC/C=C/CC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H]([C@@H](C)C(=O)O)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@H](C)N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)[C@H]2C(=O)N3CCCC[C@@H]3C(=O)N2
InChI:	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
InChI Key:	XBNDESPXQUOOBQ-LSMLZNGOSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/91663250

External links:
Guide to Pharmacology:	amphomycin
Main Source:	https://www.jstage.jst.go.jp/article/antibioticsa/15/1/15_1/_article/-char/en
Citation:	https://pubs.acs.org/doi/abs/10.1021/ja00788a040