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Cyclothiazomycin information


Cyclothiazomycin
Names
Other names
cyclothiazomycin A, 5102-II
Identifiers
CAS Number
  • 133352-26-8
3D model (JSmol)
  • Interactive image
PubChem CID
  • 16132234
InChI
  • InChI=1S/C59H64N18O14S7/c1-7-27-47(85)76-59(6)58(91)75-42(25(5)78)49(87)61-15-40(80)64-28(8-2)56(88)77-13-9-10-38(77)48(86)62-23(3)41-26(43(81)67-30(14-39(60)79)52-69-32(17-93-52)45(83)66-27)11-12-29(65-41)51-73-35(20-96-51)53-70-31(16-94-53)44(82)63-24(4)50-72-34(19-92-50)55-74-36(21-97-55)54-71-33(18-95-54)46(84)68-37(22-98-59)57(89)90/h7-8,11-12,19-21,23,25,30-33,37-38,42,78H,4,9-10,13-18,22H2,1-3,5-6H3,(H2,60,79)(H,61,87)(H,62,86)(H,63,82)(H,64,80)(H,66,83)(H,67,81)(H,68,84)(H,75,91)(H,76,85)(H,89,90)/b27-7-,28-8-/t23-,25-,30+,31+,32+,33-,37+,38+,42+,59+/m1/s1
    Key: OGUUCNCVZHZWGA-CRYGVMHLSA-N
SMILES
  • O=C([C@H]1CSC(C2=CSC(C3=CSC(C(NC([C@@H]4CSC(C5=CSC(C6=CC=C(C(N[C@@H](CC(N)=O)C7=N[C@H](C(N/C8=C\C)=O)CS7)=O)C([C@H](NC9=O)C)=N6)=N5)=N4)=O)=C)=N3)=N2)=N1)N[C@H](C(O)=O)CS[C@@](C)(C(N[C@]([C@H](O)C)([H])C(NCC(N/C(C(N%10[C@H]9CCC%10)=O)=C\C)=O)=O)=O)NC8=O
Properties
Chemical formula
C59H64N18O14S7
Molar mass 1473.71 g/mol
Melting point >210 °C (decomposes)
Solubility soluble in water, chloroform/methanol, mixed aqueous/organic solvents (DMSO/water, methanol/water, acetone/water)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The cyclothiazomycins are a group of natural products, classified as thiopeptides, which are produced by various Streptomyces species of bacteria.

These compounds are ribosomally synthesized and post-translationally modified peptides (RiPPs) and can be further classified as thiopeptides. The overall structure of the cyclothiazomycins comprises a macrocyclic bicyclic peptide containing several thiazoles and thiazolines. The cyclothiazomycins are reported to have multiple inhibitory effects ranging from decreasing blood pressure to interfering with RNA transcription; they also exhibit some antibiotic activity.

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