Structure Database (LMSD)

Common Name
dinor-12-oxo PDA
Systematic Name
(1S,2S)-3-oxo-2-(2'Z-pentenyl) cyclopent-4-enehexanoic acid
Synonyms
  • Dinor-12-oxophytodienoic acid
  • dn-OPDA
LM ID
LMFA02010018
Formula
C16H24O3
Exact Mass
Calculate m/z
264.172545
Sum Composition
FA 16:4;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Octadecanoids [FA02]
12-oxophytodienoic acid metabolites [FA0201]

Biological Context

In plants, certain unsaturated fatty acids are oxygenated and then further modified along the jasmonate pathway to produce plant hormones that are involved in senescence, flower development, mechanotransduction, and the response to herbivory.1 dinor-12-oxo-Phytodienoic acid (dinor-OPDA) is an intermediate in the synthesis of jasmonic acid from hexadecatrienoic acid.2,3 It can also be incorporated into glycerolipids and galactolipids, including certain arabidopsides.4,5

This information has been provided by Cayman Chemical

References

1. Schaller, A., and Stintzi, A. Enzymes in jasmonate biosynthesis - Structure, function, regulation. Phytochemistry 70(13-14), 1532-1538 (2009).
2. Snoeren, T.A.L., Van Poecke, R.M.P., and Dicke, M. Multidisciplinary approach to unravelling the relative contribution of different oxylipins in indirect defense of Arabidopsis thaliana. J. Chem. Ecol. 35(9), 1021-1031 (2009).
3. Kourtchenko, O., Andersson, M.A., Hamberg, M., et al. Oxo-phytodienoic acid-containing galactolipids in Arabidopsis: Jasmonate signaling dependence. Plant Physiol. 145(4), 1658-1669 (2007).
4. Gfeller, A., Dubugnon, L., Liechti, R., et al. Jasmonate biochemical pathway. Sci. Signal. 3(109), (2010).
5. Buseman, S.M., Tamura, P., Sparks, A.A., et al. Wounding stimulates the accumulation of glycerolipids containing oxophytodienoic acid and dinor-oxophytodienoic acid in Arabidopsis leaves. Plant Physiol. 142(1), 28-39 (2006).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Arabidopsis thaliana (#3702)
Magnoliopsida (#3398)
Dinor-oxo-phytodienoic acid: a new hexadecanoid signal in the jasmonate family.,
Proc Natl Acad Sci U S A, 1997
Pubmed ID: 9294235

String Representations

InChiKey (Click to copy)
SZVNKXCDJUBPQO-DWMAKUKJSA-N
InChi (Click to copy)
InChI=1S/C16H24O3/c1-2-3-5-9-14-13(11-12-15(14)17)8-6-4-7-10-16(18)19/h3,5,11-14H,2,4,6-10H2,1H3,(H,18,19)/b5-3-/t13-,14-/m0/s1
SMILES (Click to copy)
OC(CCCCC[C@H]1C=CC(=O)[C@H]1C/C=C\CC)=O

Other Databases

CHEBI ID
138434
PubChem CID
91746127
Cayman ID
10710

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 1
Aromatic Rings 0
Rotatable Bonds 9
Van der Waals Molecular Volume 288.81
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 3.75
Molar Refractivity 75.90

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Created at
29th Jul 2020
Updated at
29th Jul 2020