SML1603 Sigma-Aldrich


≥98% (HPLC)

Synonym: (S)-N-[1-{N′-Cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-1H-pyrazol-4-yl]-N-ethyl-2-hydroxyacetamide

  • Empirical Formula (Hill Notation) C22H20Cl2F2N6O3

  • Molecular Weight 525.34

  •  PubChem Substance ID 329825489



Related Categories B, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
optical activity   [α]/D -85 to -95°, c = 1 in methanol
color   white to beige
solubility   DMSO: 25 mg/mL, clear
storage temp.   2-8°C
SMILES string   ClC1=C(Cl)C=C(C2=NN(C(NC3=CC=CC(OC(F)F)=C3)=NC#N)C[C@@H]2[C@H](CC)C(CO)=O)C=C1
InChI   1S/C23H21Cl2F2N5O3/c1-2-16(20(34)11-33)17-10-32(31-21(17)13-6-7-18(24)19(25)8-13)23(29-12-28)30-14-4-3-5-15(9-14)35-22(26)27/h3-9,16-17,22,33H,2,10-11H2,1H3,(H,29,30)/t16?,17-/m1/s1



5, 25 mg in glass bottle

Biochem/physiol Actions

BAY-598 is a potent, peptide-competitive chemical probe for SET and MYND domain-containing protein 2 (SMYD2), a lysine methyl transferase inhibitor that dimethylates histone H3K36 and methylates histone H3K4. SMYD2 also methylates Lys-370 of p53, leading to decreased DNA-binding activity. SMYD2 is over-expressed in several cancers with poor prognosis. BAY-598 inhibits in vitro methylation of p53K370 with an IC50 value of 27 nM and in cells with an IC50 value < 1 μM. BAY-598 is more than 100-fold selective over other histone methyltransferases and non-epigenetic targets. BAY-598 can be used with in vivo experiments. For full characterization details, please visit the BAY-598 probe summary on the Structural Genomics Consortium (SGC) website.

BAY-369 is the negative control for the active probe, BAY-598. To request a sample of the negative control from the SGC, click here.

To learn about other SGC chemical probes for epigenetic targets, visit

Features and Benefits

BAY-598 is an epigenetic chemical probe available through a partnership with the Structural Genomics Consortium (SGC). To learn more and view other SGC epigenetic probes, visit

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at

Other Notes

BAY-598 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the BAY-598 probe summary on the Chemical Probes Portal website.

Safety & Documentation

Safety Information

GHS07  GHS07
Signal word 
Hazard statements 
Precautionary statements 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Protocols & Articles


Discover Bioactive Small Molecules for Gene Regulation

The loss of regulation of gene expression is a key component to many human disease states, including neurodegenerative disorders, autoimmune conditions and, most prominently, cancers. Regulation of g...
Keywords: Acetylations, Epigenetics, Gene expression, Genomics, Methylations, PAGE, Post translational modifications, Transcription

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