NBI-74330   Click here for help

GtoPdb Ligand ID: 839

Synonyms: (±)-NBI 74330 | NBI74330
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: NBI-74330 is a potent and selective CXCR3 antagonist [1]. CXCR3 is predominantly expressed on T helper type 1 (Th1) cells that are involved in inflammatory diseases. The endogenous ligands for CXCR3 are CXCL9, CXCL10, and CXCL11 that are produced at inflammatory sites and are pro-chemoattractant towards pathological Th1 cells.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 11
Topological polar surface area 89.69
Molecular weight 605.21
XLogP 5.69
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCOc1ccc(cc1)n1c(nc2c(c1=O)cccn2)C(N(C(=O)Cc1ccc(c(c1)C(F)(F)F)F)Cc1cccnc1)C
Isomeric SMILES CCOc1ccc(cc1)n1c(nc2c(c1=O)cccn2)C(N(C(=O)Cc1ccc(c(c1)C(F)(F)F)F)Cc1cccnc1)C
InChI InChI=1S/C32H27F4N5O3/c1-3-44-24-11-9-23(10-12-24)41-30(39-29-25(31(41)43)7-5-15-38-29)20(2)40(19-22-6-4-14-37-18-22)28(42)17-21-8-13-27(33)26(16-21)32(34,35)36/h4-16,18,20H,3,17,19H2,1-2H3
InChI Key XMRGQUDUVGRCBS-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[1-[3-(4-ethoxyphenyl)-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-2-[4-fluoro-3-(trifluoromethyl)phenyl]-N-(pyridin-3-ylmethyl)acetamide
Synonyms Click here for help
(±)-NBI 74330 | NBI74330
Database Links Click here for help
GtoPdb PubChem SID 135650695
PubChem CID 10167713
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Tocris
(±)-NBI 74330
Cat. No. 4528