Structure Database (LMSD)

Common Name
9-KOT
Systematic Name
9-oxo-10E,12Z,15Z-octadecatrienoic acid
Synonyms
LM ID
LMFA02000371
Formula
C18H28O3
Exact Mass
Calculate m/z
292.203845
Sum Composition
FA 18:4;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]
Other Octadecanoids [FA0200]

Biological Context

9-OxoOTrE is produced by the oxidation of 9-HpOTrE.1 9-OxoOTrE exhibits antimicrobial activity against plant pathogenic microorganisms including bacteria and fungi.2

This information has been provided by Cayman Chemical

References

1. Koch, T., Hoskovec, M., and Boland, W. Efficient syntheses of (10E, 12Z,15Z)-9-oxo- and (9Z,11E,15E)-13-oxo-octadecatrienoic acids; Two stress metabolites of wounded plants. Tetrahedron 58, 3271-3274 (2002).
2. 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).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Glechoma hederacea (#28509)
Magnoliopsida (#3398)
Occurrence of free and esterified lipoxygenase products in leaves of Glechoma hederacea L. and other Labiatae.,
Eur J Biochem, 1989
Pubmed ID: 2598926

String Representations

InChiKey (Click to copy)
ACHDMUPTZYZIGR-CUHSZNQNSA-N
InChi (Click to copy)
InChI=1S/C18H28O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3-,8-6-,14-11+
SMILES (Click to copy)
C(CCCCCCCC(=O)/C=C/C=C\C/C=C\CC)(=O)O

Other Databases

CHEBI ID
142251
PubChem CID
11380794
Cayman ID
10009215

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 0
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 333.13
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 4.84
Molar Refractivity 87.29

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Created at
21st Jul 2020
Updated at
21st Jul 2020