Structure Database (LMSD)
Common Name
12-oxo-PDA
Systematic Name
(1S,2S)-3-oxo-2-(2'Z-pentenyl)cyclopent-4-eneoctanoic acid
Synonyms
- (9S,13S)-12-oxo-phytodienoic acid
3D model of 12-oxo-PDA
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
12-oxo Phytodienoic acid (OPDA) is a biologically active, immediate precursor of 7-epi jasmonic acid.1 In addition to its link with jasmonic acid activity, OPDA appears to play an independent role in mediating resistance to pathogens and pests. As an endogenous signal transducer, OPDA has been shown to increase alkaloid biosynthesis in E. californica cell cultures, increase tendril coiling of B. dioica, and suppress jasmonic acid-induced programmed cell death in a conditional A. flu mutant.2
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. Böttcher, C., and Pollmann, S. Plant oxylipins: Plant responses to 12-oxo-phytodienoic acid are governed by its specific structural and functional properties. FEBS J. 276(17), 4693-4704 (2009).
String Representations
InChiKey (Click to copy)
PMTMAFAPLCGXGK-JMTMCXQRSA-N
InChi (Click to copy)
InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-/t15-,16-/m0/s1
SMILES (Click to copy)
C(CCCCCCC(=O)O)[C@H]1C=CC(=O)[C@H]1C/C=C\CC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
1
Aromatic Rings
0
Rotatable Bonds
11
Van der Waals Molecular Volume
323.41
Topological Polar Surface Area
54.37
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
3
logP
4.53
Molar Refractivity
85.13
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