Structure via PubChem · Public domain (PubChem)
Telomestatin
Sign in to saveTelomestatin is a macrocyclic chemical compound that acts by inhibiting the telomerase activity of in vitro cancer cells. It was first isolated from the bacteria Streptomyces anulatus. Telomestatin induces the formation of basket-type G-quadruplex (G4) structures from hybrid-type G-quadruplexes in the telomeric region. Upon formation of G4 structure there will be a decrease in the activity of the telomerase, which is involved in the replication of the telomeres and as a result the cell dies due to Hayflick type senescence.
Chemical data
- Formula
- C26H14N8O7S
- Molecular weight
- 582.5 g/mol
- IUPAC name
- (1R)-4,8-dimethyl-3,7,11,15,19,23,27-heptaoxa-31-thia-33,34,35,36,37,38,39,40-octazanonacyclo[28.2.1.12,5.16,9.110,13.114,17.118,21.122,25.126,29]tetraconta-2(40),4,6(39),8,10(38),12,14(37),16,18(36),20,22(35),24,26(34),28,30(33)-pentadecaene
- SMILES
- CC1=C2C3=NC(=C(O3)C)C4=NC(=CO4)C5=NC(=CO5)C6=NC(=CO6)C7=NC(=CO7)C8=NC(=CO8)C9=N[C@@H](CS9)C(=N2)O1
- InChIKey
- YVSQVYZBDXIXCC-INIZCTEOSA-N
- XLogP
- 2
- Polar surface area
- 220 Ų
- H-bond donors
- 0
- H-bond acceptors
- 16
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- alkaloid
- Mass
- 582.070615788
Show 4 more facts
- chemical formula
- C₂₆H₁₄N₈O₇S
- isomeric SMILES
- CC1=C(C2=NC(C3=NC(C4=NC(C5=NC(C6=NC(C7=NC(C8=N[C@@]9([H])CS8)=CO7)=CO6)=CO5)=CO4)=CO3)=C(C)O2)N=C9O1
- canonical SMILES
- N1=C2OC=C1C3=NC(=CO3)C4=NC(=CO4)C5=NC(C6=NC(C7=NC(C8=NC(=CO8)C9=NC2=CO9)=C(O7)C)=C(O6)C)CS5
- Commons category
- Telomestatin
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Telomestatin is a macrocyclic chemical compound that acts by inhibiting the telomerase activity of in vitro cancer cells. It was first isolated from the bacteria Streptomyces anulatus. Telomestatin induces the formation of basket-type G-quadruplex (G4) structures from hybrid-type G-quadruplexes in the telomeric region. Upon formation of G4 structure there will be a decrease in the activity of the telomerase, which is involved in the replication of the telomeres and as a result the cell dies due to Hayflick type senescence.
==References==
Excerpted from Wikipedia’s “Telomestatin” article, available under the CC BY-SA 4.0 licence.