AB680   Click here for help

GtoPdb Ligand ID: 10707

Synonyms: AB-680
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AB680 is a reversible, slow-onset competitive inhibitor of CD73 (ecto-5'-nucleotidase) [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 6
Rotatable bonds 9
Topological polar surface area 216.11
Molecular weight 580.07
XLogP 0.19
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES O[C@@H]1[C@H](O)[C@H](O[C@H]1n1ncc2c1nc(Cl)cc2N[C@H](c1ccccc1F)C)COP(=O)(CP(=O)(O)O)O
Isomeric SMILES O[C@@H]1[C@H](O)[C@H](O[C@H]1n1ncc2c1nc(Cl)cc2N[C@H](c1ccccc1F)C)COP(=O)(CP(=O)(O)O)O
InChI InChI=1S/C20H24ClFN4O9P2/c1-10(11-4-2-3-5-13(11)22)24-14-6-16(21)25-19-12(14)7-23-26(19)20-18(28)17(27)15(35-20)8-34-37(32,33)9-36(29,30)31/h2-7,10,15,17-18,20,27-28H,8-9H2,1H3,(H,24,25)(H,32,33)(H2,29,30,31)/t10-,15+,17+,18+,20+/m0/s1
InChI Key MFYLCAMJNGIULC-KCVUFLITSA-N
Immunopharmacology Comments
CD73 hydrolyzes AMP to adenosine, and thus regulates the extracellular concentration of adenosine. It is expressed by lymphocytes, endothelial, and epithelial cells, and expression is upregulated under hypoxic or inflammatory conditions, and in various cancers. Elevated CD73 in tumours leads to increased levels of adenosine which impairs antitumour immunity and promotes tumour growth and metastasis. Mechanisms to inhibit CD73 activity are being exploited for immuno-oncology potential, and are exemplified by the progress of the anti-CD73 monoclonal oleclumab and the small molecule inhibitor AB680 into clinical trials as treatments for solid tumours.