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

仕様

同義語

仕様と純度

10mM in DMSO

生化学的・生理学的メカニズム

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 )

保管条件

Protected from light,Store at -80°C

入荷

Dry ice packs + Cold packs

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名前と識別子

パブケム・シド

528774155

パブケム・シド・ウル

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

カノニカル・スマイル

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-

異性体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ドイツ

RTECS

XN6300100

分子量

1664.89

Reaxy-Rn

24868543

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24868543&ln=

ドキュメント

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詳細データ

Taxonomic Classification

Taxonomy Tree

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

Kingdom	Organic compounds
Superclass	Organic acids and derivatives
分類	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
説明	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

3 D構造

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レビュー

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感度	Light sensitive;Moisture sensitive
融点（°C）	246-256°C
分子量	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

保管・配送

品質書類

文献的裏付け

概要

仕様