S-4048   Click here for help

GtoPdb Ligand ID: 8845

Synonyms: S 4048
Compound class: Synthetic organic
Comment: S-4048 is a chlorogenic acid (PubChem CID 1794427) derivative which acts as a very potent inhibitor of glucose-6-phosphate translocase (G6P T1; SLC37A4). SLC37A4 acts as a gatekeeper to transport glucose 6-phosphate into the endoplasmic reticulum and therefore plays an important role in the regulation of blood glucose levels.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 144
Molecular weight 603.18
XLogP 4.55
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C(C=C(n1cnc2c1cccn2)c1ccccc1)OC1CC(OCC2CC2c2ccc(cc2)Cl)(CC(C1O)O)C(=O)O
Isomeric SMILES O=C(/C=C(\n1cnc2c1cccn2)/c1ccccc1)O[C@@H]1C[C@@](OC[C@@H]2C[C@@H]2c2ccc(cc2)Cl)(C[C@H]([C@H]1O)O)C(=O)O
InChI InChI=1S/C32H30ClN3O7/c33-22-10-8-19(9-11-22)23-13-21(23)17-42-32(31(40)41)15-26(37)29(39)27(16-32)43-28(38)14-25(20-5-2-1-3-6-20)36-18-35-30-24(36)7-4-12-34-30/h1-12,14,18,21,23,26-27,29,37,39H,13,15-17H2,(H,40,41)/b25-14-/t21-,23+,26+,27+,29+,32-/m0/s1
InChI Key MYXPHMOLFCUDIL-MLFVSVOESA-N
References
1. Charkoudian LK, Farrella BP, Khosla C. (2012)
Natural product inhibitors of glucose-6-phosphate translocase.
Medchemcomm, 3 (8): 926-931.