compound 14a [PMID: 34795866]   Click here for help

GtoPdb Ligand ID: 11837

Compound class: Synthetic organic
Comment: This compound is a small molecule, orally active apelin receptor agonist [1]. Its pharmacodynamic effects are similar to those produced by the peptide agonist (Pyr1)apelin-13 in a rat heart failure model.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 106.26
Molecular weight 512.18
XLogP 6.36
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCCCc1nc(=O)c(c(n1c1c(OC)cccc1OC)O)C(=O)N1CC[C@H](C1)c1ccc(cn1)Cl
Isomeric SMILES C(CCC)c1n(c(c(c(=O)n1)C(=O)N1C[C@@H](CC1)c1ncc(cc1)Cl)O)c1c(cccc1OC)OC
InChI InChI=1S/C26H29ClN4O5/c1-4-5-9-21-29-24(32)22(26(34)31(21)23-19(35-2)7-6-8-20(23)36-3)25(33)30-13-12-16(15-30)18-11-10-17(27)14-28-18/h6-8,10-11,14,16,34H,4-5,9,12-13,15H2,1-3H3/t16-/m1/s1
InChI Key KSQCOKRJNWPXJJ-MRXNPFEDSA-N
References
1. Pi Z, Johnson JA, Meng W, Phillips M, Schumacher WA, Bostwick JS, Gargalovic PS, Onorato JM, Generaux CN, Wang T et al.. (2021)
Identification of 6-Hydroxypyrimidin-4(1H)-one-3-carboxamides as Potent and Orally Active APJ Receptor Agonists.
ACS Med Chem Lett, 12 (11): 1766-1772. [PMID:34795866]