Thiostrepton

Thiostrepton
Names
IUPAC name
N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-2-[(1R,8S,11Z,18S,25S,26R,53S,59S)-37-butan-2-yl-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-31-[(1S)-1-hydroxyethyl]-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide
Other names
Alaninamide, Bryamycin, Thiactin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.014.304
EC Number
  • 215-734-9
UNII
  • InChI=1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15-/t26-,30-,31-,32-,33+,34+,35+,39+,45+,47-,48-,49-,51-,52+,53+,71+,72+/m0/s1
    Key: NSFFHOGKXHRQEW-AIHSUZKVSA-N
  • C[C@@H](O)[C@@](C)(O)[C@@H](C2=NC6=CS2)NC(C1CSC(/C(NC([C@@H](NC(C3=CS[C@]([C@]4(NC([C@@H](NC(C(NC([C@H](C)NC%10=O)=O)=C)=O)C)=O)C(C5=CSC([C@H]([C@@H](C)OC(C8=CC([C@H](C)O)=C(C=CC(N[C@]([H])%10[C@H](CC)C)[C@@H]9O)C9=N8)=O)NC6=O)=N5)N=C(C7=NC(C(NC(C(NC(C(N)=O)=C)=O)=C)=O)=CS7)CC4)=N3)=O)[C@@H](C)O)=O)=C/C)=N1)=O
Properties
C72H85N19O18S5
Molar mass 1664.83 g/mol
Appearance White to off-white powder
Melting point 246 to 256 °C (475 to 493 °F; 519 to 529 K)
Insoluble
Solubility in other solvents Soluble in CHCl3, CH2Cl2, dioxane, pyridine, glacial acetic acid, DMF. Practically insoluble in the lower alcohols, nonpolar organic solvents, diluted aqueous acids or bases. May be dissolved by methanolic acid or base, but with decomposition.
Hazards
GHS labelling:
Warning
H302
P264, P270, P301+P312, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Thiostrepton is a natural cyclic oligopeptide antibiotic of the thiopeptide class, derived from several strains of streptomycetes, such as Streptomyces azureus and Streptomyces laurentii. Thiostrepton is a natural product of the ribosomally synthesized and post-translationally modified peptide (RiPP) class.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.