Structure Database (LMSD)

Common Name
Docebenone
Systematic Name
2-(12-hydroxydodeca-5,10-diyn-1-yl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
Synonyms
  • 2,3,5-trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-1,4-benzoquinone
  • 2-(12-Hydroxy-5,10-dodecadiynyl)-3,5,6-trimethyl-p-benzoquinone
  • 2-(12-hydroxydodeca-5,10-diynyl)-3,5,6-trimethyl-1,4-benzoquinone
  • 6-(12-hydroxydodeca-5,10-diyn-1-yl)-2,3,5-trimethyl-1,4-benzoquinone
  • AA-861
  • AA861
LM ID
LMFA05000652
Formula
C21H26O3
Exact Mass
Calculate m/z
326.188195
Sum Composition
FOH 21:9;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Phenolic lipids [PK15]
Alkyl hydroquinones and derivatives [PK1505]
Fatty Acyls [FA]
Fatty alcohols [FA05]

Biological Context

AA-861 is an inhibitor of 5-lipoxygenase (5-LO; IC50 = 0.8 µM).1 It is greater than 100-fold selective for 5-LO over 12-LO and cyclooxygenase (COX). AA-861 inhibits the production of 5-HETE and leukotriene B4 (LTB4) induced by A23187 with IC50 values of 0.03 and 0.08 µM, respectively, in isolated rat peritoneal macrophages.2 It reduces paw edema, pleurisy, and cell infiltration induced by carrageenan in rats when administered at a dose of 80 mg/kg. AA-861 (20 mg/kg) reduces ovalbumin-induced bronchoconstriction in an ovalbumin-sensitized guinea pig model of experimental allergic asthma.

This information has been provided by Cayman Chemical

References

1. Ashida, Y., Saijo, T., Kuriki, H., et al. Pharmacological profile of AA-861, a 5-lipoxygenase inhibitor. Prostaglandins 26(6), 955-972 (1983).
2. Yoshimoto, T., Yokoyama, C., Ochi, K., et al. 2,3,5-Trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-l,4-benzoquinone (AA861), a selective inhibitor of the 5-lipoxygenase reaction and the biosynthesis of slow-reacting substance of anaphylaxis. Biochim. Biophys. Acta 713(2), 470-473 (1982).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
2,3,5-Trimethyl-6-(12-hydroxy-5,10-dodecadiynyl)-1,4-benzoquinone (AA861), a selective inhibitor of the 5-lipoxygenase reaction and the biosynthesis of slow-reacting substance of anaphylaxis.,
Biochim Biophys Acta, 1982
Pubmed ID: 6817808

String Representations

InChiKey (Click to copy)
WDEABJKSGGRCQA-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C21H26O3/c1-16-17(2)21(24)19(18(3)20(16)23)14-12-10-8-6-4-5-7-9-11-13-15-22/h22H,5,7-10,12,14-15H2,1-3H3
SMILES (Click to copy)
C(CCCC#CCCCC#CCO)C1=C(C)C(=O)C(C)=C(C)C1=O

Other Databases

KEGG ID
C01349
CHEBI ID
2340
PubChem CID
1967
Cayman ID
13263

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 1
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 364.75
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 3.81
Molar Refractivity 96.53

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Created at
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Updated at
27th Jan 2025