diroleuton   Click here for help

GtoPdb Ligand ID: 9775

Synonyms: 8,11,14-Eicosatrienoic acid | DGLA | dihomo-gamma-linolenic acid | DS107 | Homo-gamma-linolenic acid
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Diroleuton (dihomo-gamma-linolenic acid; DGLA) is a 20-carbon-chain fatty acid that is structurally very similar to arachadonic acid (AA). It competes with AA for binding to the substrate binding sites of the COX and lipoxygenase enzymes, and this effect reduces the production of inflammatory mediators (eicosanoids) from AA. DGLA can be converted to PGE1 and eicosapentaenoic acid (EPA), the latter being a precursor for the synthesis of series-3 prostaglandins, series-5 leukotrienes and series-3 thromboxanes.

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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 2
Hydrogen bond donors 1
Rotatable bonds 15
Topological polar surface area 37.3
Molecular weight 306.26
XLogP 8.68
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 CCCCCC=CCC=CCC=CCCCCCCC(=O)O
Isomeric SMILES CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
InChI InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
InChI Key HOBAELRKJCKHQD-QNEBEIHSSA-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. Gani OABSM, Sylte I. (2009)
Molecular recognition of long chain fatty acids by peroxisome proliferator-activated receptor.
Med Chem Res, 18: 8-19.
2. Maltarollo VG, Honorio KM. (2013)
Molecular properties of fatty acids related to PPAR binding and metabolic diseases.
Med Chem Res, 22: 3126-3133.
3. Vakharia PP, Silverberg JI. (2018)
New therapies for atopic dermatitis: Additional treatment classes.
J Am Acad Dermatol, 78 (3S1): S76-S83. [PMID:29248520]