compound 21b [PMID: 31944697]   Click here for help

GtoPdb Ligand ID: 10640

Compound class: Synthetic organic
Comment: Compound 21b is reported as a selective inhibitor of acid sphingomyelinase (ASM; SMPD1) [1]. It crosses the blood-brain-barrier in a rat model and has predicted value as an antidepressant based on outcomes from in vivo behavioural models of depression.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 84.59
Molecular weight 344.06
XLogP 3.97
No. Lipinski's rules broken 0
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Canonical SMILES ONC(=O)c1onc(c1)OCc1ccc(cc1)c1ccc(cc1)Cl
Isomeric SMILES ONC(=O)c1onc(c1)OCc1ccc(cc1)c1ccc(cc1)Cl
InChI InChI=1S/C17H13ClN2O4/c18-14-7-5-13(6-8-14)12-3-1-11(2-4-12)10-23-16-9-15(24-20-16)17(21)19-22/h1-9,22H,10H2,(H,19,21)
Bioactivity Comments
Compound 21b does not inhibit neutral sphingomyelinase [1].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
sphingomyelin phosphodiesterase 1 Hs Inhibitor Inhibition 6.5 pIC50 - 1
pIC50 6.5 (IC50 3.2x10-7 M) [1]
Description: Inhibition of sphingomyelin phosphodiesterase 1 (ASM) in an extract from hepatocellular carcinoma (Huh 7) cells.