thiostrepton

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.

Chemical data

Formula: C72H85N19O18S5
Molecular weight: 1664.9 g/mol
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
SMILES: CCC(C)C1C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)N[C@]23CCC(=N[C@@H]2C4=CSC(=N4)[C@H]([C@H](OC(=O)C5=NC6=C(C=CC([C@@H]6O)N1)C(=C5)[C@H](C)O)C)NC(=O)C7=CSC(=N7)[C@@H](NC(=O)C8CSC(=N8)/C(=C/C)/NC(=O)[C@@H](NC(=O)C9=CSC3=N9)[C@@H](C)O)[C@@](C)([C@@H](C)O)O)C1=NC(=CS1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C)C
InChIKey: NSFFHOGKXHRQEW-GLAXDNAISA-N
XLogP: 0.6
Polar surface area: 701 Å²
H-bond donors: 17
H-bond acceptors: 31
Formal charge: 0

via PubChem

Research

687 papers

Thiostrepton induces ferroptosis in pancreatic cancer cells through STAT3/GPX4 signalling.Cell death & disease · 2022
Thiostrepton: multifaceted biological activities and its applications in treatment of inflammatory diseases.Inflammopharmacology · 2025
Thiostrepton suppresses triple-negative breast cancer through downregulating c-FLIP/SMAD2/3 signaling pathway.Journal of Asian natural products research · 2024
Thiostrepton, a natural compound that triggers heat shock response and apoptosis in human cancer cells: a proteomics investigation.Advances in experimental medicine and biology · 2014
How thiostrepton was made in the laboratory.Angewandte Chemie (International ed. in English) · 2012

via PubMed

Wikidata facts

Mass: 1663.492351879999
Has use: medication

Show 6 more facts

chemical formula: C₇₂H₈₅N₁₉O₁₈S₅
canonical SMILES: CCC(C)C1C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)NC23CCC(=NC2C4=CSC(=N4)C(C(OC(=O)C5=NC6=C(C=CC(C6O)N1)C(=C5)C(C)O)C)NC(=O)C7=CSC(=N7)C(NC(=O)C8CSC(=N8)C(=CC)NC(=O)C(NC(=O)C9=CSC3=N9)C(C)O)C(C)(C(C)O)O)C1=NC(=CS1)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C)C
isomeric SMILES: CC[C@H](C)[C@@H]1N[C@@H]2C=CC3=C(N=C(C=C3[C@H](C)O)C(=O)O[C@H](C)[C@@H]4NC(=O)C5=CSC(=N5)[C@@H](NC(=O)[C@H]6CSC(=N6)\C(NC(=O)[C@@H](NC(=O)C7=CSC(=N7)[C@]8(CCC(=N[C@@H]8C9=CSC4=N9)C%10=NC(=CS%10)C(=O)NC(=C)C(=O)NC(=C)C(N)=O)NC(=O)[C@H](C)NC(=O)C(=C)NC(=O)[C@H](C)NC1=O)[C@@H](C)O)=C\C)[C@](C)(O)[C@@H](C)O)[C@H]2O
subject has role: antibiotic
medical condition treated: dermatitis
Commons category: Thiostrepton

Sources (4)

via Wikidata · CC0

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