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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
SMILES / InChI / InChIKey
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
International Nonproprietary Names Click here for help
INN number INN
10359 diroleuton
Synonyms Click here for help
8,11,14-Eicosatrienoic acid | DGLA | dihomo-gamma-linolenic acid | DS107 | Homo-gamma-linolenic acid
Database Links Click here for help
CAS Registry No. 1783-84-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL465183
GtoPdb PubChem SID 354702248
PubChem CID 5280581
RCSB PDB Ligand LAX
Search Google for chemical match using the InChIKey HOBAELRKJCKHQD-QNEBEIHSSA-N
Search Google for chemicals with the same backbone HOBAELRKJCKHQD
Search PubMed clinical trials diroleuton
Search PubMed titles diroleuton
Search PubMed titles/abstracts diroleuton
Search UniChem for chemical match using the InChIKey HOBAELRKJCKHQD-QNEBEIHSSA-N
Search UniChem for chemicals with the same backbone HOBAELRKJCKHQD