palmoxiric acid   Click here for help

GtoPdb Ligand ID: 2683

Synonyms: (±) acid 3 [1] | 2-tetradecylglycidic acid | MCN-3802 | MCN-3802-21-98
Compound class: Metabolite
Comment: Palmoxiric acid is an orally active inhibitor of long-chain fatty acid oxidation with hypoglycemic activity. The major activity of this compound is as a carnitine palmitoyl transferase (CPT) inhibitor. The majority of the biological activity resides with the R enantiomer, which is converted to its CoA ester in vivo [1].
The INN-assigned compound palmoxiric acid is a racemic mixture of two enantiomers. The structure shown here does not specify stereochemistry and represents the mixture.
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 3
Hydrogen bond donors 1
Rotatable bonds 14
Topological polar surface area 49.83
Molecular weight 284.24
XLogP 6.59
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCCCCCCCCCCC1(CO1)C(=O)O
Isomeric SMILES CCCCCCCCCCCCCCC1(CO1)C(=O)O
InChI InChI=1S/C17H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(15-20-17)16(18)19/h2-15H2,1H3,(H,18,19)
InChI Key FGIJQXGDQVNWKH-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Ho W, Tarhan O, Kiorpes TC, Tutwiler GF, Mohrbacher RJ. (1987)
Resolution of (+/-)-2-tetradecyloxiranecarboxylic acid. Absolute configuration and chiral synthesis of the hypoglycemic R enantiomer and biological activity of enantiomers.
J Med Chem, 30 (6): 1094-7. [PMID:3585906]