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CAS 73957-86-5

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α-Avoparcin

Description:
α-Avoparcin is a glycopeptide antibiotic that is structurally related to vancomycin and is primarily used in veterinary medicine, particularly in livestock, to promote growth and prevent infections. It exhibits antibacterial activity against Gram-positive bacteria, including certain strains of Staphylococcus and Enterococcus. The compound works by inhibiting cell wall synthesis, which is crucial for bacterial growth and survival. α-Avoparcin is known for its effectiveness in enhancing feed efficiency and weight gain in animals. However, its use has raised concerns regarding the development of antibiotic resistance, particularly in human pathogens, leading to its ban in several countries for agricultural purposes. The substance is typically administered through feed or water and is characterized by its stability under various conditions, making it suitable for use in animal husbandry. Its chemical structure includes a complex arrangement of amino acids and sugar moieties, contributing to its biological activity and pharmacological properties.
Formula:C89H102ClN9O36
InChI:InChI=1S/C89H102ClN9O36/c1-31-66(106)47(91)27-56(124-31)132-77-38-12-20-51(46(90)22-38)129-53-24-39-23-52(78(53)135-89-79(73(113)70(110)55(30-101)131-89)133-57-28-48(92)67(107)32(2)125-57)127-42-17-9-36(10-18-42)76(134-88-75(115)72(112)69(109)54(29-100)130-88)64(98-80(116)59(93-4)34-7-15-43(16-8-34)128-87-74(114)71(111)68(108)33(3)126-87)84(120)94-60(35-5-13-40(102)14-6-35)81(117)96-62(39)83(119)95-61-37-11-19-49(104)44(21-37)58-45(25-41(103)26-50(58)105)63(86(122)123)97-85(121)65(77)99-82(61)118/h5-26,31-33,47-48,54-57,59-77,79,87-89,93,100-115H,27-30,91-92H2,1-4H3,(H,94,120)(H,95,119)(H,96,117)(H,97,121)(H,98,116)(H,99,118)(H,122,123)
InChI key:InChIKey=XQKGPVCSSWFILW-UHFFFAOYSA-N
SMILES:O(C=1C2=CC3=CC1OC=4C=CC(=CC4)C(OC5OC(CO)C(O)C(O)C5O)C(NC(C(NC)C6=CC=C(OC7C(O)C(O)C(O)C(C)O7)C=C6)=O)C(=O)NC(C(=O)NC3C(=O)NC8C=9C=C(C=%10C(C(C(O)=O)NC(=O)C(C(OC%11CC(N)C(O)C(C)O%11)C=%12C=C(Cl)C(O2)=CC%12)NC8=O)=CC(O)=CC%10O)C(O)=CC9)C%13=CC=C(O)C=C%13)C%14C(OC%15CC(N)C(O)C(C)O%15)C(O)C(O)C(CO)O%14
Synonyms:
  • (3′′R,4′′R)-22-O-(3-Amino-2,3,6-trideoxy-α-L-ribo-hexopyranosyl)-3-de(2-amino-2-oxoethyl)-10-dechloro-3′′-demethyl-49-de[4-methyl-2-(methylamino)-1-oxopentyl]-49-[(2R)-2-[4-[(6-deoxy-α-L-mannopyranosyl)oxy]phenyl]-2-(methylamino)acetyl]-3-(4-hydroxyphenyl)-7-O-α-D-mannopyranosylvancomycin
  • Avoparcin α
  • Vancomycin, 22-O-(3-amino-2,3,6-trideoxy-α-L-ribo-hexopyranosyl)-3-de(2-amino-2-oxoethyl)-10-dechloro-3′′-demethyl-49-de[4-methyl-2-(methylamino)-1-oxopentyl]-49-[(2R)-2-[4-[(6-deoxy-α-L-mannopyranosyl)oxy]phenyl]-2-(methylamino)acetyl]-3-(4-hydroxyphenyl)-7-O-α-D-mannopyranosyl-, (3′′R,4′′R)-
  • Vancomycin, 22-O-(3-amino-2,3,6-trideoxy-α-L-ribo-hexopyranosyl)-3-de(2-amino-2-oxoethyl)-10-dechloro-3′′-demethyl-49-de[4-methyl-2-(methylamino)-1-oxopentyl]-49-[(2R)-[4-[(6-deoxy-α-L-mannopyranosyl)oxy]phenyl](methylamino)acetyl]-3-(4-hydroxyphenyl)-7-O-α-D-mannopyranosyl-, (3′′R,4′′R)-
  • 22H-8,11:18,21-Dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-1H,16H-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine, avoparcin α deriv.
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