HSD1590   

GtoPdb Ligand ID: 10424

Compound class: Synthetic organic
Comment: HSD1590 is a boronic acid-containing Rho-associated kinase (ROCK) inhibitor [1]. In vitro, it is more potent than netarsudil at binding to or inhibiting ROCK enzymatic activities.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 91.26
Molecular weight 359.14
XLogP 3.9
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1c(cccc1B(O)O)c1nc2ccc3c(c2c2c1CCC2)cn[nH]3
Isomeric SMILES COc1c(cccc1B(O)O)c1nc2ccc3c(c2c2c1CCC2)cn[nH]3
InChI InChI=1S/C20H18BN3O3/c1-27-20-13(6-3-7-15(20)21(25)26)19-12-5-2-4-11(12)18-14-10-22-24-16(14)8-9-17(18)23-19/h3,6-10,25-26H,2,4-5H2,1H3,(H,22,24)
InChI Key WTZMCUOBQPTERK-UHFFFAOYSA-N
Bioactivity Comments
HSD1590 inhibits migration of MDA-MB-231 triple negative breast cancer cells in vitro, whereas netarsudil does not [1]. HSD1590 is also less cytotoxic (even at high concentration) towards MDA-MB-231 cells than netarsudi, suggesting potential anti-metastatic action.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Rho associated coiled-coil containing protein kinase 1 Hs Inhibitor Inhibition 8.8 pKd - 1
pKd 8.8 (Kd 1.65x10-9 M) [1]
Rho associated coiled-coil containing protein kinase 2 Hs Inhibitor Inhibition 7.9 pKd - 1
pKd 7.9 (Kd 1.125x10-8 M) [1]
Rho associated coiled-coil containing protein kinase 2 Hs Inhibitor Inhibition 9.3 pIC50 - 1
pIC50 9.3 (IC50 5.1x10-10 M) [1]
Rho associated coiled-coil containing protein kinase 1 Hs Inhibitor Inhibition 8.9 pIC50 - 1
pIC50 8.9 (IC50 1.22x10-9 M) [1]