Structure Database (LMSD)

Common Name
8Z,11Z,14Z-heptadecatrienal
Systematic Name
8Z,11Z,14Z-heptadecatrienal
Synonyms
LM ID
LMFA06000111
Formula
C17H28O
Exact Mass
Calculate m/z
248.214015
Sum Composition
FAL 17:3
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]
Fatty aldehydes [FA06]

Biological Context

8(Z),11(Z),14(Z)-Heptadecatrienal is a polyunsaturated fatty aldehyde. It is formed from α-linolenic acid via a 2(R)-hydroperoxy-9(Z),12(Z),15(Z)-octadecatrienoic acid intermediate.1 It is also a degradation product of 2(R)-hydroperoxy linolenic acid. 8(Z),11(Z),14(Z)-Heptadecatrienal (100 µM) is active against the plant pathogenic bacteria P. syringae.2 It protects Arabidopsis plants against infection by the bacteria Pst DC3000 when injected into the leaves at a concentration of 150 µM prior to bacterial inoculation.3

This information has been provided by Cayman Chemical

References

1. Prost, I., Dhondt, S., Rothe, G., et al. Evaluation of the antimicrobial activities of plant oxylipins supports their involvement in defense against pathogens. Plant Physiol. 139(4), 1902-1913 (2005).
2. Hamberg, M., Sanz, A., and Castresana, C. α-Oxidation of fatty acids in higher plants. Identification of a pathogen-inducible oxygenase (PIOX) as an α-dioxygenase and biosynthesis of 2-hydroperoxylinolenic acid. The Journal of Biological Chemisty 274(35), 24503-24513 (1999).
3. Vicente, J., Cascón, T., Vicedo, B., et al. Role of 9-lipoxygenase and α-dioxygenase oxylipin pathways as modulators of local and systemic defense. Mol. Plant 5(4), 914-928 (2012).

String Representations

InChiKey (Click to copy)
NIPNNUONNZABRE-PDBXOOCHSA-N
InChi (Click to copy)
InChI=1S/C17H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18/h3-4,6-7,9-10,17H,2,5,8,11-16H2,1H3/b4-3-,7-6-,10-9-
SMILES (Click to copy)
C(CCCCCC/C=C\C/C=C\C/C=C\CC)=O

Other Databases

KEGG ID
C16343
CHEBI ID
76151
PubChem CID
6430107
Cayman ID
10005154

Calculated Physicochemical Properties

Heavy Atoms 18
Rings 0
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 300.89
Topological Polar Surface Area 17.07
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 1
logP 5.38
Molar Refractivity 80.71

Admin

Created at
-
Updated at
-