compound 1b [PMID: 18078750]   Click here for help

GtoPdb Ligand ID: 8627

Compound class: Synthetic organic
Comment: Compound 1b was synthesised in a medicinal chemisrty study aiming to discover novel angiotensin-converting enzyme 2 inhibitors (ACE2) [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 105.2
Molecular weight 405.14
XLogP 4.88
No. Lipinski's rules broken 0
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Canonical SMILES SC(C(=O)NC(C(=O)O)Cc1ccc(cc1)c1ccccc1)Cc1ccccc1
Isomeric SMILES S[C@@H](C(=O)N[C@H](C(=O)O)Cc1ccc(cc1)c1ccccc1)Cc1ccccc1
InChI InChI=1S/C24H23NO3S/c26-23(22(29)16-17-7-3-1-4-8-17)25-21(24(27)28)15-18-11-13-20(14-12-18)19-9-5-2-6-10-19/h1-14,21-22,29H,15-16H2,(H,25,26)(H,27,28)/t21-,22+/m0/s1
Bioactivity Comments
Of the enxymes tested, compound 1b has weakest inhibitory activity against ACE2 (Ki 1400nM) and is most potent against neprilysin (MME) [1]. Angiotensin-converting enzyme (ACE) and pancreatic carboxypeptidase A1 (CPA1) are inhibited moderately [1].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Neutral endopeptidase Primary target of this compound Hs Inhibitor Inhibition 8.9 pKi - 1
pKi 8.9 (Ki 1.3x10-9 M) [1]
Carboxypeptidase A1 (pancreatic) Hs Inhibitor Inhibition 6.5 pKi - 1
pKi 6.5 (Ki 3.1x10-7 M) [1]