Structure Database (LMSD)
Common Name
(3R,7S)-iso-jasmonic acid
Systematic Name
(1R,2S)-3-oxo-2-(2'Z-pentenyl)-cyclopentaneacetic acid
Synonyms
- (3R,7S)-epi-jasmonic acid
- (+)-7-iso-jasmonic acid
3D model of (3R,7S)-iso-jasmonic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
(±)-7-epi Jasmonic acid is the major metabolite of the 12-oxo phytodienoic acid pathway of the metabolism of 13(S)-hydroperoxy linolenic acid in plants. Initially synthesized as (+)-7-epi jasmonic acid, this more active and biologically relevant form of the hormone quickly epimerizes to the more stable isomer (−)-7-jasmonic acid.1,2 (±)-7-epi Jasmonic acid is a plant growth regulator that activates various signal transduction pathways with both growth promoting and inhibitory functions, perhaps in response to stress.3,4
This information has been provided by Cayman Chemical
References
2. Wasternack, C., and Parthier, B. Jasmonate-signalled plant gene expression. Trends in Plant Sci. 2, 302-307 (1997).
String Representations
InChiKey (Click to copy)
ZNJFBWYDHIGLCU-QKMQQOOLSA-N
InChi (Click to copy)
InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10+/m1/s1
SMILES (Click to copy)
C(C[C@@H]1[C@H](C/C=C\CC)C(=O)CC1)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
15
Rings
1
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
222.25
Topological Polar Surface Area
54.37
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
3
logP
2.41
Molar Refractivity
57.52
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Updated at
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