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
LM ID
LMFA02020003
Formula
Exact Mass
Calculate m/z
210.125595
Sum Composition
Status
Curated


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

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

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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