Compound ID | 573

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Glycothiohexide

Synonym(s): Glycothiohexide alpha

Class: Glycothiopeptide

Spectrum of activity: Gram-positive
Details of activity: Low MICs in in vitro studies against MRSA and vancomycin- resistant Enterococcus faecalis
Description: Steinberg DA, Bernan VS, Montenegro DA, et al. Glycothiohexides, a novel antibioitics produced by Sebekia sp. LL-14E065: Taxonomy, fermentation and biological evaluation. 33rd-Intersci-Conf-Antimicrobial-Agents-Chemother 1993; 224.
Institute where first reported: American cyanamid Co., USA
Year first mentioned: 1993
Highest developmental phase: Preclinical
Development status: Inactive
Reason Dropped: Failed to protect mice models depite low MIC values
Chemical structure(s):
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Molecular weight: 1368.55
Iso. SMILES: C[C@H]1[C@H]([C@@](C[C@@H](O1)OC2C3C4C5=NC(=CS5)C(=O)NC(CSC(=O)C6=C(CO3)C7=C(COC2=O)C=CC=C7N6)C8=NC(=CS8)C9=NC(=C(C=C9C%10=NC(=CS%10)C(=O)NC(C(=O)N/C(=C(/C)\OC)/C%11=NC(=CS%11)C(=O)N4)C(C)O)O)C%12=NC(=CS%12)C(=O)N)(C)O)N(C)C
InChI Key: SQNIUXZFYJCFRU-XALLAZSSSA-N
Can. SMILES: CC(C1C(=O)N/C(=C(/C)\OC)/C2=NC(=CS2)C(=O)NC3C4C(C(=O)OCC5=CC=CC6=C5C(=C(C(=O)SCC(C7=NC(=CS7)C8=NC(=C(C=C8C9=NC(=CS9)C(=O)N1)O)C%10=NC(=CS%10)C(=O)N)NC(=O)C%11=CSC3=N%11)N6)CO4)O[C@H]%12C[C@@](C)([C@@H]([C@H](C)O%12)N(C)C)O)O
InChI: InChI=1S/C58H57N13O15S6/c1-21(72)37-50(78)69-38(22(2)82-7)53-65-32(19-90-53)49(77)70-42-43-44(86-35-12-58(4,81)45(71(5)6)23(3)85-35)56(79)84-13-24-9-8-10-27-36(24)26(14-83-43)40(60-27)57(80)92-20-33(61-47(75)30-18-91-55(42)66-30)52-62-28(15-88-52)39-25(51-64-31(17-87-51)48(76)68-37)11-34(73)41(67-39)54-63-29(16-89-54)46(59)74/h8-11,15-19,21,23,33,35,37,42-45,60,72-73,81H,12-14,20H2,1-7H3,(H2,59,74)(H,61,75)(H,68,76)(H,69,78)(H,70,77)/b38-22-/t21?,23-,33?,35-,37?,42?,43?,44?,45+,58-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/136714935
Citation: https://www.jstage.jst.go.jp/article/antibiotics1968/47/8/47_8_887/_pdf/-char/en

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