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Chaetocin

CAS No.:
28097-03-2
Catalog Number:
AG00BEA7
Molecular Formula:
C30H28N6O6S4
Molecular Weight:
696.8399
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$291
- +
5mg
98%
1 week
United States
$807
- +
10mg
99+%
1 week
United States
$1007
- +
Product Description
Catalog Number:
AG00BEA7
Chemical Name:
Chaetocin
CAS Number:
28097-03-2
Molecular Formula:
C30H28N6O6S4
Molecular Weight:
696.8399
MDL Number:
MFCD00133163
IUPAC Name:
(1S,3R,11R,14S)-14-(hydroxymethyl)-3-[(1S,3R,11R,14S)-14-(hydroxymethyl)-18-methyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-trien-3-yl]-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione
InChI:
InChI=1S/C30H28N6O6S4/c1-33-21(39)27-11-25(15-7-3-5-9-17(15)31-19(25)35(27)23(41)29(33,13-37)45-43-27)26-12-28-22(40)34(2)30(14-38,46-44-28)24(42)36(28)20(26)32-18-10-6-4-8-16(18)26/h3-10,19-20,31-32,37-38H,11-14H2,1-2H3/t19-,20-,25+,26+,27+,28+,29+,30+/m1/s1
InChI Key:
PZPPOCZWRGNKIR-PNVYSBBASA-N
SMILES:
OCC12SSC3(N(C1=O)C1Nc4c(C1(C3)C13CC56N(C3Nc3c1cccc3)C(=O)C(SS5)(N(C6=O)C)CO)cccc4)C(=O)N2C
Properties
Complexity:
1400  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
0
Exact Mass:
696.095g/mol
Formal Charge:
0
Heavy Atom Count:
46  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
696.83g/mol
Monoisotopic Mass:
696.095g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
247A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2  
Literature
Title Journal
Arsenic silences hepatic PDK4 expression through activation of histone H3K9 methylatransferase G9a. Toxicology and applied pharmacology 20160801
Chaetocin inhibits IBMX-induced melanogenesis in B16F10 mouse melanoma cells through activation of ERK. Chemico-biological interactions 20160205
Oncoepigenomics: making histone lysine methylation count. European journal of medicinal chemistry 20121001
Histone methyltransferase inhibitors induce HIV-1 recovery in resting CD4(+) T cells from HIV-1-infected HAART-treated patients. AIDS (London, England) 20120731
Inhibition of histone H3K9 methyltransferases by gliotoxin and related epipolythiodioxopiperazines. The Journal of antibiotics 20120501
Anti-leukemia activity of chaetocin via death receptor-dependent apoptosis and dual modulation of the histone methyl-transferase SUV39H1. Leukemia 20120401
The anticancer effects of chaetocin are independent of programmed cell death and hypoxia, and are associated with inhibition of endothelial cell proliferation. British journal of cancer 20120117
The Suv39H1 methyltransferase inhibitor chaetocin causes induction of integrated HIV-1 without producing a T cell response. FEBS letters 20111116
Epigenetic regulation of HIV-1 transcription. Epigenomics 20110801
Hypoxia-inducible factor inhibitors: a survey of recent patented compounds (2004 - 2010). Expert opinion on therapeutic patents 20110201
Antihepatoma activity of chaetocin due to deregulated splicing of hypoxia-inducible factor 1α pre-mRNA in mice and in vitro. Hepatology (Baltimore, Md.) 20110101
General approach to epipolythiodiketopiperazine alkaloids: total synthesis of (+)-chaetocins A and C and (+)-12,12'-dideoxychetracin A. Journal of the American Chemical Society 20101020
Unnatural enantiomer of chaetocin shows strong apoptosis-inducing activity through caspase-8/caspase-3 activation. Bioorganic & medicinal chemistry letters 20100901
Remodeling of nuclear architecture by the thiodioxoxpiperazine metabolite chaetocin. Experimental cell research 20100610
Assessing the trypanocidal potential of natural and semi-synthetic diketopiperazines from two deep water marine-derived fungi. Bioorganic & medicinal chemistry 20100401
Total synthesis of (+)-chaetocin and its analogues: their histone methyltransferase G9a inhibitory activity. Journal of the American Chemical Society 20100331
The anticancer agent chaetocin is a competitive substrate and inhibitor of thioredoxin reductase. Antioxidants & redox signaling 20090501
Chemical probes for histone-modifying enzymes. Nature chemical biology 20081001
Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress. Blood 20070315
Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9. Nature chemical biology 20050801
Properties