Structure Database (LMSD)
Common Name
Etheroleic acid
Systematic Name
12-(1'E-Hexaenyloxy)-9Z,11E-dodecadienoic acid
Synonyms
3D model of Etheroleic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Etheroleic acid is a divinyl ether oxylipin.1,2 It is a metabolite of linolenic acid that is formed in plants via 13-lipoxygenase-mediated formation of 13(S)-HpODE or (±)13-HpODE followed by conversion to the divinyl ether by divinyl ether synthase. Etheroleic acid (30 µM) is fungicidal against the powdery mildew B. graminis on the second leaves of barley seedlings.3
This information has been provided by Cayman Chemical
References
1. Grechkin, A.N., Ilyasov, A.V., and Hamberg, M. On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs. Eur. J. Biochem. 245(1), 137-142 (1997).
2. Hamberg, M. Biosynthesis of new divinyl ether oxylipins in Ranunculus plants. Lipids 37(4), 427-433 (2002).
3. Cowley, T., and Walters, D. Local and systemic effects of oxylipins on powdery mildew infection in barley. Pest Manag. Sci. 61(6), 572-576 (2005).
References
String Representations
InChiKey (Click to copy)
NQNHRHWFZHFAAH-XSWVPMOFSA-N
InChi (Click to copy)
InChI=1S/C18H30O3/c1-2-3-4-13-16-21-17-14-11-9-7-5-6-8-10-12-15-18(19)20/h9,11,13-14,16-17H,2-8,10,12,15H2,1H3,(H,19,20)/b11-9-,16-13+,17-14+
SMILES (Click to copy)
C(CCCCCCC/C=C\C=C\O/C=C/CCCC)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
335.77
Topological Polar Surface Area
46.53
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
3
logP
5.59
Molar Refractivity
87.98
Admin
Created at
10th Aug 2020
Updated at
9th Jun 2022