ISA-2011B   Click here for help

GtoPdb Ligand ID: 8444

Compound class: Synthetic organic
Comment: Patent search with this structure reveals SCHEMBL10020974 ID matching a structure (Analogue 1) in patent WO2010149944 [3]. ISA-2011B is being evaluated pre-clinically as a potential anti-prostate cancer therapeutic [5].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 74.87
Molecular weight 423.1
XLogP 2.08
No. Lipinski's rules broken 0
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Canonical SMILES Clc1ccc2c(c1)c(c[nH]2)C1N2C(=O)CN(C(=O)C2Cc2c1cc1OCOc1c2)C
Isomeric SMILES Clc1ccc2c(c1)c(c[nH]2)[C@H]1N2C(=O)CN(C(=O)[C@@H]2Cc2c1cc1OCOc1c2)C
InChI InChI=1S/C22H18ClN3O4/c1-25-9-20(27)26-17(22(25)28)4-11-5-18-19(30-10-29-18)7-13(11)21(26)15-8-24-16-3-2-12(23)6-14(15)16/h2-3,5-8,17,21,24H,4,9-10H2,1H3/t17-,21-/m0/s1
No information available.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
PIP5K1A is responsible for the production of PIP2 (phosphatidylinositol 4,5-bisphosphate, PtdIns-4,5-P2) [2], which is subsequently converted to PIP3 (phosphatidylinositol 3,4,5-trisphosphate, PtdIns(3,4,5)P3), an activator of the AKT family of serine/threonine kinases [1,4]. Elevated AKT activity is frequently observed in human cancer cells. Inhibition of PIP5K1A would therefore be expected to reduce PIP2 levels and AKT activity, with potential anti-cancer effects.