MI-3   Click here for help

GtoPdb Ligand ID: 8103

Compound class: Synthetic organic
Comment: MI-3 inhibits the interaction between MLL oncoproteins (re-arranged lysine (K)-specific methyltransferases) and the tumour suppressor protein menin (MEN1, O00255) [1]. MI-3 represents a novel molecular mechanism with potential application in the treatment of aggressive leukemias with MLL rearrangements.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 98.16
Molecular weight 375.16
XLogP 3.42
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CC(c1sc2c(c1)c(ncn2)N1CCN(CC1)C1=NCC(S1)(C)C)C
Isomeric SMILES CC(c1sc2c(c1)c(ncn2)N1CCN(CC1)C1=NCC(S1)(C)C)C
InChI InChI=1S/C18H25N5S2/c1-12(2)14-9-13-15(20-11-21-16(13)24-14)22-5-7-23(8-6-22)17-19-10-18(3,4)25-17/h9,11-12H,5-8,10H2,1-4H3
InChI Key FUGQNAUKABUDQI-UHFFFAOYSA-N
References
1. Grembecka J, He S, Shi A, Purohit T, Muntean AG, Sorenson RJ, Showalter HD, Murai MJ, Belcher AM, Hartley T et al.. (2012)
Menin-MLL inhibitors reverse oncogenic activity of MLL fusion proteins in leukemia.
Nat Chem Biol, 8 (3): 277-84. [PMID:22286128]
2. Hughes CM, Rozenblatt-Rosen O, Milne TA, Copeland TD, Levine SS, Lee JC, Hayes DN, Shanmugam KS, Bhattacharjee A, Biondi CA et al.. (2004)
Menin associates with a trithorax family histone methyltransferase complex and with the hoxc8 locus.
Mol Cell, 13 (4): 587-97. [PMID:14992727]
3. Yokoyama A, Wang Z, Wysocka J, Sanyal M, Aufiero DJ, Kitabayashi I, Herr W, Cleary ML. (2004)
Leukemia proto-oncoprotein MLL forms a SET1-like histone methyltransferase complex with menin to regulate Hox gene expression.
Mol Cell Biol, 24 (13): 5639-49. [PMID:15199122]