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
Bioactivity Comments
Chaetocin is reported to inhibit SUV39H1 both directly, and indirectly via a reactive oxygen species (ROS)-dependent mechanism [4]. In acute myeloid leukemia (AML) cells the outcome of chaetocin exposure is death receptor-dependent apoptosis [1].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
suppressor of variegation 3-9 homolog 1 Hs Inhibitor Inhibition 6.1 – 7.0 pIC50 - 2-3
pIC50 6.1 – 7.0 (IC50 8x10-7 – 1.1x10-7 M) [2-3]