Compound ID | 3593

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Aridicin A

Class: Glycopeptide

Spectrum of activity: Gram-positive
Details of activity: Active against Enterococcus faecalis and Clostridium spp.; cell wall synthesis inhibitor
Description: Natural product from Kibdelosporangiium aridum; natural analogues reported; shows inferior efficacy to vancomycin in mice infected with Staphylococcus aureus, Enterococcus faecalis, and Streptococcus pyogenes but shows good protection when used as prophylaxis
Institute where first reported: Smith Kline & French Laborcatories, Philadelphia, Pennsylvania 19101 USA
Year first mentioned: 1985
Development status: Experimental
Chemical structure(s):
Click here for structure editor
Molecular weight: 1789.37
Iso. SMILES: CCCCCCCCCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=C3C=C4C=C2OC5=C(C=C(C=C5Cl)[C@H]([C@H]6C(=O)N[C@@H](C7=C(C(=CC(=C7)O)O[C@@H]8[C@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C9=C(C=CC(=C9)[C@H](C(=O)N6)NC(=O)[C@@H]4NC(=O)[C@@H]1C2=C(C(=CC(=C2)OC2=C(C=CC(=C2)[C@H](C(=O)N[C@H]([C@@H](C2=CC(=C(O3)C=C2)Cl)O)C(=O)N1)NC)O)O)Cl)O)C(=O)O)O)Cl)C(=O)O)O)O
InChI Key: SFGRLMCXHBJMSU-PKMCQBQCSA-N
Can. SMILES: CCCCCCCCCC(=O)N[C@@H]1[C@H]([C@@H]([C@@H](C(=O)O)O[C@H]1OC2=C3C=C4C=C2OC5=CC=C(C=C5Cl)[C@H]([C@@H]6C(=O)N[C@@H](C7=CC(=CC(=C7Cl)O)OC8=CC(=CC=C8O)[C@H](C(=O)N6)NC)C(=O)N[C@H]4C(=O)N[C@@H]9C%10=CC=C(C(=C%10)C%11=C(C=C(C=C%11[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](C%12=CC(=C(C(=C%12)Cl)O3)Cl)O)NC9=O)O)O[C@@H]%13[C@H]([C@H]([C@@H]([C@@H](CO)O%13)O)O)O)O)O)O)O
InChI: InChI=1S/C81H82Cl4N8O30/c1-3-4-5-6-7-8-9-10-51(99)87-61-65(103)67(105)71(79(115)116)123-80(61)122-70-48-22-32-23-49(70)119-69-40(83)19-33(20-41(69)84)63(101)60-77(112)91-58(78(113)114)37-24-34(95)25-47(120-81-68(106)66(104)64(102)50(28-94)121-81)52(37)36-17-29(11-14-42(36)96)55(73(108)93-60)88-74(109)56(32)89-75(110)57-38-26-35(27-44(98)53(38)85)117-46-21-30(12-15-43(46)97)54(86-2)72(107)92-59(76(111)90-57)62(100)31-13-16-45(118-48)39(82)18-31/h11-27,50,54-68,71,80-81,86,94-98,100-106H,3-10,28H2,1-2H3,(H,87,99)(H,88,109)(H,89,110)(H,90,111)(H,91,112)(H,92,107)(H,93,108)(H,113,114)(H,115,116)/t50-,54-,55-,56-,57+,58+,59-,60+,61-,62-,63-,64-,65-,66+,67+,68+,71+,80-,81+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/86278229
Citations:
  • https://pubs.acs.org/doi/epdf/10.1021/ja00271a042?ref=article_openPDF
  • https://journals.asm.org/doi/10.1128/aac.28.5.660

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