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
C12H18O3
Exact Mass
Calculate m/z
210.125595
Sum Composition
FA 12:3;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Octadecanoids [FA02]
Jasmonic acids [FA0202]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Oxo fatty acids [FA0106]
Carbocyclic fatty acids [FA0114]

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

1. Hamberg, M., and Gardner, H.W. Oxylipin pathway to jasmonates: Biochemistry and biological significance. Biochim. Biophys. Acta 1165(1), 1-18 (1992).
2. Wasternack, C., and Parthier, B. Jasmonate-signalled plant gene expression. Trends in Plant Sci. 2, 302-307 (1997).
3. Holbrook, L., Tung, P., Ward, K., et al. Importance of the chiral centers of jasmonic acid in the responses of plants. Activities and antagonism between natural and synthetic analogs. Plant Physiol. 114(2), 419-428 (1997).
4. Browse, J., and Howe, G.A. New weapons and a rapid response against insect attack. Plant Physiol. 146(3), 832-838 (2008).

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
C16317
CHEBI ID
18435
PubChem CID
7251183
Cayman ID
88320

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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