Thiostrepton is a cyclic peptide antibiotic, densely packed with thiazoles and other structurally intriguing moieties. Thiostrepton exhibits antibiotic activity through blockade of ribosome turnover after an elongation step in protein synthesis by inhibiting both the dissociation of elongation factor G (EF-G) from the ribosome and the release of inorganic phosphate from EF-G following GTP hydrolysis. Thiostrepton is also described to show efficacy against cancer cell growth through downregulation of the forkhead box M1 (FOXM1) transcription factor, commonly overexpressed in many malignancies. Thiostrepton is an inhibitor of FOXM1
A protein synthesis-inhibiting antibiotic

Specifications

Sinónimos

Especificaciones y pureza

≥98%, from Streptomyces laurentii

Mecanismos bioquímicos y fisiológicos

Peptide antibiotic that prevents the binding of elongation factor G (EF-G) and GTP to the 50S ribosomal subunit.Potent Gram-positive antibiotic. Protein synthesis inhibitor. Inhibits FOXM1. Shows antitumor effects in vivo. Enhances cisplatin ( Asc 1398 )

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C, Desiccated

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one week. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Nombres e identificadores

Pubchem Sid	504768412
Pubchem Sid Url	https://pubchem.ncbi.nlm.nih.gov/substance/504768412
Sonrisas canónicas	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
IUPAC Name	N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-2-[(11Z)-37-butan-2-yl-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,31-bis(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
InChIKey	NSFFHOGKXHRQEW-BXVAPQLOSA-N
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-
Isómeros 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(=C/C)/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
WGK Alemania	3
RTECS	XN6300100
Peso molecular	1664.89
Reaxy-Rn	24868543
Reaxys-RN_link_address	https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24868543&ln=

Documentation

📋 Safety Data Sheet (SDS)

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Advanced Data

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Organic acids and derivatives
  - Clase Carboxylic acids and derivatives
    - Subclass Amino acids, peptides, and analogues
      - Level5 Peptides
        Level6 Cyclic peptides

Kingdom	Organic compounds
Superclass	Organic acids and derivatives
Clase	Carboxylic acids and derivatives
Subclass	Amino acids, peptides, and analogues
Intermediate Tree Nodes	Peptides
Direct Parent	Cyclic peptides
Alternative Parents	Pyridinecarboxylic acids Tetrahydropyridines 2,4-disubstituted thiazoles Aralkylamines Imidothiolactones Thiazolines Tertiary alcohols Cyclic carboximidic acids Heteroaromatic compounds Secondary alcohols Amino acids and derivatives Carboxylic acid esters Ketimines Lactones Dialkylamines Polyols Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Organic oxides Aromatic alcohols
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Cyclic alpha peptide - Pyridine carboxylic acid - 2,4-disubstituted 1,3-thiazole - Tetrahydropyridine - Aralkylamine - Pyridine - Imidothiolactone - Azole - Tertiary alcohol - Heteroaromatic compound - Thiazole - Meta-thiazoline - Cyclic carboximidic acid - Carboxylic acid ester - Ketimine - Lactone - Secondary alcohol - Amino acid or derivatives - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidic acid - Carboximidic acid derivative - Azacycle - Secondary aliphatic amine - Organoheterocyclic compound - Oxacycle - Polyol - Secondary amine - Imine - Aromatic alcohol - Amine - Organonitrogen compound - Organooxygen compound - Alcohol - Organic oxide - Hydrocarbon derivative - Organic nitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
Descripción	This compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
External Descriptors	Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

Estructura 3D

Objetivos asociados (humanos)

A498 (42825 Activities)

Lot Number	Certificate Type	Fecha	Articulo
G2209391	Certificate of Analysis	Apr 07, 2026	T102394
G2209389	Certificate of Analysis	Apr 07, 2026	T102394
L2103291	Certificate of Analysis	Sep 09, 2025	T102394
I2403008	Certificate of Analysis	Jun 18, 2022	T102394

Solubilidad	Soluble in DMSO (10 mg/ml), chloroform (10 mg/ml), dioxane, pyridine, glacial acetic acid, and DMF. Insoluble in water
Sensibilidad	Light sensitive;Moisture sensitive
Punto de fusión (°C)	246-256°C
Peso molecular	1664.900 g/mol
XLogP3	0.600
Hydrogen Bond Donor Count	17
Hydrogen Bond Acceptor Count	31
Rotatable Bond Count	12
Exact Mass	1663.49 Da
Monoisotopic Mass	1663.49 Da
Topological Polar Surface Area	701.000 Å²
Heavy Atom Count	114
Formal Charge	0
Complexity	3940.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	17
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	1
Covalently-Bonded Unit Count	1

Thiostrepton - ≥98%, from Streptomyces laurentii , CAS No.1393-48-2

Why this grade

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Quality documents

Literature proof

Descripción general

Specifications

Documentation

📋 Safety Data Sheet (SDS)

✅ Certificate of Analysis (COA)

📊 Datasheet

🔬 Specification Sheet

Advanced Data

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