compound 19a [PMID: 26506089]   Click here for help

GtoPdb Ligand ID: 9842

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 19a is the most potent of a series of STAT6 inhibitors reported by Mandal et al. (2015) [1]. STAT6 inhibitors are being developed for their potential to inhibit the expression of genes contributing to asthma. Compound 19a is a phosphopeptide mimic that blocks interaction of the IL-4 and IL-13 receptors with the SH2 domain of STAT6, thereby preventing the downstream transcriptional sequelae of STAT6 activation. The structure is claimed in patent WO2014182928 [2].
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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 13
Topological polar surface area 146.29
Molecular weight 745.14
XLogP 5.27
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES Ic1ccc(cc1)N(C(=O)C1CCCN1C(=O)C(C(C)(C)C)NC(=O)C=C(c1ccc(cc1)OP(=O)(O)O)C)c1ccccc1
Isomeric SMILES Ic1ccc(cc1)N(C(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)(C)C)NC(=O)/C=C(/c1ccc(cc1)OP(=O)(O)O)\C)c1ccccc1
InChI InChI=1S/C33H37IN3O7P/c1-22(23-12-18-27(19-13-23)44-45(41,42)43)21-29(38)35-30(33(2,3)4)32(40)36-20-8-11-28(36)31(39)37(25-9-6-5-7-10-25)26-16-14-24(34)15-17-26/h5-7,9-10,12-19,21,28,30H,8,11,20H2,1-4H3,(H,35,38)(H2,41,42,43)/b22-21+/t28-,30+/m0/s1
InChI Key CGLGRSOJPUXNFA-YVXBOAIISA-N
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Compound class Synthetic organic
IUPAC Name Click here for help
[4-[(E)-4-[[(2S)-1-[(2S)-2-[(4-iodophenyl)-phenylcarbamoyl]pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]amino]-4-oxobut-2-en-2-yl]phenyl] dihydrogen phosphate
Database Links Click here for help
ChEMBL Ligand CHEMBL3741938
GtoPdb PubChem SID 363894136
PubChem CID 86292328
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