chaetocin   

GtoPdb Ligand ID: 8388

Comment: Chaetocin is a fungal mycotoxin specifically inhibiting the histone methyltransferase (HMT), suppressor of variegation 3-9 homolog 1 (SUV39H1) [2-3]. SUV39H1 is the main enzyme responsible for the trimethylation of lysine 9 in histone H3.
We show the chemical structure here without any stereochemical specification. PubChem records various stereoisomers of this naturally ocurring metabolite.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 12
Hydrogen bond donors 4
Rotatable bonds 3
Topological polar surface area 246.96
Molecular weight 696.1
XLogP -1.21
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES OCC12SSC3(N(C1=O)C1Nc4c(C1(C3)C13CC56N(C3Nc3c1cccc3)C(=O)C(SS5)(N(C6=O)C)CO)cccc4)C(=O)N2C
Isomeric SMILES OCC12SSC3(N(C1=O)C1Nc4c(C1(C3)C13CC56N(C3Nc3c1cccc3)C(=O)C(SS5)(N(C6=O)C)CO)cccc4)C(=O)N2C
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
InChI Key PZPPOCZWRGNKIR-UHFFFAOYSA-N
References
1. Chaib H, Nebbioso A, Prebet T, Castellano R, Garbit S, Restouin A, Vey N, Altucci L, Collette Y. (2012)
Anti-leukemia activity of chaetocin via death receptor-dependent apoptosis and dual modulation of the histone methyl-transferase SUV39H1.
Leukemia, 26 (4): 662-74. [PMID:21979880]
2. Cherblanc FL, Chapman KL, Brown R, Fuchter MJ. (2013)
Chaetocin is a nonspecific inhibitor of histone lysine methyltransferases.
Nat. Chem. Biol., 9 (3): 136-7. [PMID:23416387]
3. Greiner D, Bonaldi T, Eskeland R, Roemer E, Imhof A. (2005)
Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9.
Nat. Chem. Biol., 1 (3): 143-5. [PMID:16408017]
4. Isham CR, Tibodeau JD, Jin W, Xu R, Timm MM, Bible KC. (2007)
Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress.
Blood, 109 (6): 2579-88. [PMID:17090648]