rimacalib   Click here for help

GtoPdb Ligand ID: 9364

Synonyms: SMP-114
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Rimacalib (SMP-114) is an isoxazole derivative inhibitor of Ca2+/calmodulin-dependent protein kinase II (CaMKII) [2], CAMKII being an established pharmacological target for chronic inflammatory pain [1], as well as being involved in modulating synaptic plasticity and learning and memory processes.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 76.88
Molecular weight 394.18
XLogP 4.27
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NC(=Nc1onc(c1)C(c1ccc(c(c1)F)c1ccccc1)C)N1CCOCC1
Isomeric SMILES N/C(=N\c1onc(c1)[C@H](c1ccc(c(c1)F)c1ccccc1)C)/N1CCOCC1
InChI InChI=1S/C22H23FN4O2/c1-15(17-7-8-18(19(23)13-17)16-5-3-2-4-6-16)20-14-21(29-26-20)25-22(24)27-9-11-28-12-10-27/h2-8,13-15H,9-12H2,1H3,(H2,24,25)/t15-/m0/s1
InChI Key MYTIJGWONQOOLC-HNNXBMFYSA-N
References
1. Luo F, Yang C, Chen Y, Shukla P, Tang L, Wang LX, Wang ZJ. (2008)
Reversal of chronic inflammatory pain by acute inhibition of Ca2+/calmodulin-dependent protein kinase II.
J Pharmacol Exp Ther, 325: 267-75. [PMID:18178903]
2. Westra J, Brouwer E, Bouwman E, Doornbos-van der Meer B, Posthumus MD, van Leeuwen MA, Limburg PC, Ueda Y, Kallenberg CG. (2009)
Role for CaMKII inhibition in rheumatoid arthritis: effects on HIF-1-induced VEGF production by rheumatoid synovial fibroblasts.
Ann N Y Acad Sci, 1173: 706-11. [PMID:19758219]