CRX-555

Ligand id: 10091

Name: CRX-555

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 21
Hydrogen bond donors 6
Rotatable bonds 73
Topological polar surface area 315.96
Molecular weight 1402.97
XLogP 22.5
No. Lipinski's rules broken 4

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
(2S)-3-[(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-[[(3R)-3-octanoyloxytetradecanoyl]amino]-4-[(3R)-3-octanoyloxytetradecanoyl]oxy-5-phosphonooxyoxan-2-yl]oxy-2-[[(3R)-3-octanoyloxytetradecanoyl]amino]propanoic acid
Synonyms
CRX555 | N-[(3R)-3-(Octanoyloxy)myristoyl]-O-[2-[[(3R)-3-(octanoyloxy)myristoyl]amino]-3-O-[(3R)-3-(octanoyloxy)myristoyl]-4-O-phosphono-2-deoxy-beta-D-glucopyranosyl]-L-serine
Comments
CRX-555 is a synthetic Toll-like receptor 4 (TLR4) partial agonist from the Corixa Corporation [9]. It is one of a series of lipid A mimetic aminoalkyl glucosaminide phosphate compounds that were synthesised with different length secondary acyl chains. CRX-555 has 8 carbon atoms in each of its 3 secondary acyl chains. The chemical structures for aminoalkyl glucosaminide phosphate lipid A mimetics including CRX-555 were originally claimed in patent US6303347B1 (now expired) TLR4 as potential adjuvants and immunoeffectors [8]. A later patent (WO2008128997A1 [4]) claims these compounds for prophylactic and therapeutic applications in autoimmune diseases. The partial agonist effect of CRX-555 was demonstrated in HeLa cells transfected with TLR4/MD-2/CD14 and an IL-8 luciferase promoter construct. While CRX-527 gave a maximum stimulation of almost 60-fold (at 10μg/ml), the maximum stimulation by CRX-555 at this concentration was only ~25-fold [9].
Database Links
GtoPdb PubChem SID 381118801
PubChem CID 87596969
Search Google for chemical match using the InChIKey WNFNQTGQGFHQLU-NRBIUWCVSA-N
Search Google for chemicals with the same backbone WNFNQTGQGFHQLU
Search UniChem for chemical match using the InChIKey WNFNQTGQGFHQLU-NRBIUWCVSA-N
Search UniChem for chemicals with the same backbone WNFNQTGQGFHQLU