Structure Database (LMSD)

Common Name
Jasmonic acid
Systematic Name
(1R,2R)-3-oxo-2-(pent-2Z-enyl)-cyclopentaneacetic acid
Synonyms
  • (-)-Jasmonic acid
  • (3R,7R)-Jasmonic acid
LM ID
LMFA02020001
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 BMRB ID(NMR) spectrum
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

(±)-Jasmonic acid is a plant growth regulator and a derivative of α-linolenic acid .1 It decreases chlorophyll levels in green and etiolated barley leaf segments when used at concentrations of 10 and 50 µM.2 (±)-Jasmonic acid (10-1,000 µM) inhibits elongation of rice seedlings.3 It increases germination of S. hermonthica seeds by 26% when used at a concentration of 1,000 µM.4

This information has been provided by Cayman Chemical

References

1. Creelman, R.A., and Mullet, J.E. Biosynthesis and action of jasmonates in plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 48, 355-381 (1997).
2. Miersch, O., Herrmann, H., Kramell, H.-M., et al. Biological activity of jasmonic acid glucosyl ester. Biochem. Physiol. Pflanz. 182(5), 425-428 (1987).
3. Yamane, H., Sugawara, J., Suzuki, Y., et al. Synthesis of jasmonic acid related compounds and their structure-activity relationships on the growth of rice seedings. Agr. Biol. Chem. 44(12), 2857-2864 (1980).
4. Yoneyama, K., Ogasawara, M., Takeuchi, Y., et al. Effect of jasmonates and related copmonuds on seed germination of Orobanche minor smith and Striga hermonthica (del.) benth. Biosci. Biotechnol. Biochem. 62(7), 1448-1450 (1998).

String Representations

InChiKey (Click to copy)
ZNJFBWYDHIGLCU-HWKXXFMVSA-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)
C1C(=O)[C@H](C/C=C\CC)[C@@H](CC(O)=O)C1

Other Databases

Wikipedia
Jasmonic_acid
KEGG ID
C08491
HMDB ID
HMDB0032797
CHEBI ID
18292
PubChem CID
5281166
Cayman ID
88300
PDB ID
JAA

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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