olesoxime   Click here for help

GtoPdb Ligand ID: 8542

Synonyms: cholest-4-en-3-one, oxime | TRO-19622 | TRO19622
Compound class: Synthetic organic
Comment: Olesoxime is an investigational cholesterol-like compound with potential as a therapeutic for amyotrophic lateral sclerosis (ALS) [2,4] or spinal muscular atrophy (SMA).
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 0
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 32.59
Molecular weight 399.35
XLogP 10.75
No. Lipinski's rules broken 1
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 ON=C1CCC2(C(=C1)CCC1C2CCC2(C1CCC2C(CCCC(C)C)C)C)C
Isomeric SMILES O/N=C\1/CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCCC(C)C)C)C)C
InChI InChI=1S/C27H45NO/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28-29)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25,29H,6-16H2,1-5H3/b28-21-/t19-,22+,23-,24+,25+,26+,27-/m1/s1
InChI Key QNTASHOAVRSLMD-FCARAQADSA-N
References
1. Bernardi P, Bonaldo P. (2008)
Dysfunction of mitochondria and sarcoplasmic reticulum in the pathogenesis of collagen VI muscular dystrophies.
Ann N Y Acad Sci, 1147: 303-11. [PMID:19076452]
2. Bordet T, Buisson B, Michaud M, Drouot C, Galéa P, Delaage P, Akentieva NP, Evers AS, Covey DF, Ostuni MA et al.. (2007)
Identification and characterization of cholest-4-en-3-one, oxime (TRO19622), a novel drug candidate for amyotrophic lateral sclerosis.
J Pharmacol Exp Ther, 322 (2): 709-20. [PMID:17496168]
3. Lemasters JJ, Theruvath TP, Zhong Z, Nieminen AL. (2009)
Mitochondrial calcium and the permeability transition in cell death.
Biochim Biophys Acta, 1787 (11): 1395-401. [PMID:19576166]
4. Martin LJ. (2010)
Olesoxime, a cholesterol-like neuroprotectant for the potential treatment of amyotrophic lateral sclerosis.
IDrugs, 13 (8): 568-80. [PMID:20721828]