navamepent   Click here for help

GtoPdb Ligand ID: 9463

Synonyms: RX-10045
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Navamepent (RX-10045) is a stable resolvin E1 analogue, that is being investigated for clinical efficacy in occular inflammation [3]. Chemically this is an isopropyl ester prodrug of resolvin E1 (an agonist of the chemerin receptor). The chemical structure is claimed in patent US20140275247A1 (as Example 1001) [2]. Findings from animal studies are reported in [1] and [4].
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 2
Rotatable bonds 9
Topological polar surface area 66.76
Molecular weight 304.17
XLogP 2.51
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 C#CCC(C=CC=CC#CC(CCCC(=O)OC(C)C)O)O
Isomeric SMILES C#CC[C@H](/C=C/C=C/C#C[C@H](CCCC(=O)OC(C)C)O)O
InChI InChI=1S/C18H24O4/c1-4-10-16(19)11-7-5-6-8-12-17(20)13-9-14-18(21)22-15(2)3/h1,5-7,11,15-17,19-20H,9-10,13-14H2,2-3H3/b6-5+,11-7+/t16-,17-/m1/s1
InChI Key ZVOCIIHCJJEFRQ-BHXBHYJPSA-N
References
1. Cholkar K, Gilger BC, Mitra AK. (2016)
Topical delivery of aqueous micellar resolvin E1 analog (RX-10045).
Int J Pharm, 498 (1-2): 326-34. [PMID:26706439]
2. Gjorstrup P, Schwartz CE. (2016)
Compositions and methods for the treatment of inflammation.
Patent number: US20140275247A1. Assignee: ANIDA PHARMA Inc. Priority date: 13/04/2013. Publication date: 19/04/2016.
3. Hesselink JM, Chiosi F, Costagliola C. (2016)
Resolvins and aliamides: lipid autacoids in ophthalmology - what promise do they hold?.
Drug Des Devel Ther, 10: 3133-3141. [PMID:27729772]
4. Torricelli AA, Santhanam A, Agrawal V, Wilson SE. (2014)
Resolvin E1 analog RX-10045 0.1% reduces corneal stromal haze in rabbits when applied topically after PRK.
Mol Vis, 20: 1710-6. [PMID:25558174]