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Preuve documentaire

Cité dans 3 publications à comité de lecture couvrant la chromatographie, la synthèse organique et les réactions de couplage croisé.

Vue d’ensemble

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

Spécifications

Synonymes

Spécifications et pureté

10mM in DMSO

Mécanismes biochimiques et physiologiques

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 )

Conditions de stockage de stockage

Protected from light,Store at -80°C

Expédié en

Dry ice packs + Cold packs

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

Pubchem Sid

528774155

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/528774155

Sourires canoniques

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-

Isomères 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 Allemagne

RTECS

XN6300100

Poids moléculaire

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

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Document complet couvrant les dangers, la manipulation, le stockage et la conformité réglementaire.

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Données avancées

Taxonomic Classification

Taxonomy Tree

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

Kingdom	Organic compounds
Superclass	Organic acids and derivatives
Classe	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
Description	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

Structure 3D

Cibles associées (humaines)

A498 (42825 Activities)

Sensibilité	Light sensitive;Moisture sensitive
Point de fusion (°C)	246-256°C
Poids moléculaire	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 - 10mM in DMSO , CAS No.1393-48-2

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