Structure Database (LMSD)

Common Name
9Z-traumatiin
Systematic Name
12-oxo-9Z-dodecenoic acid
Synonyms
LM ID
LMFA01060167
Formula
C12H20O3
Exact Mass
Calculate m/z
212.141245
Sum Composition
FA 12:2;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Oxo fatty acids [FA0106]
Unsaturated fatty acids [FA0103]

Biological Context

12-oxo-9(Z)-Dodecenoic acid is an ω-oxoacid and a metabolite of the ω-6 PUFA linoleic acid and the ω-3 PUFA α-linolenic acid .1 It is formed from these PUFAs via lipoxygenase-produced 13-hydroperoxy intermediates by hydroperoxide lyase in plants. 12-oxo-9(Z)-Dodecenoic acid (100 µM) is active against the plant pathogenic oomycete P. parasitica.2

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. Vick, B.A., and Zimmerman, D.C. Oxidative systems for modification of fatty acids: The lipoxygenase pathway. The biochemistry of plants: A comprehensive treatise 9, 53-90 (1987).

Reactions

Filter by species:
ⓘ Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Psidium guajava (#120290)
Magnoliopsida (#3398)
The "heterolytic hydroperoxide lyase" is an isomerase producing a short-lived fatty acid hemiacetal.,
Biochim Biophys Acta, 2004
Pubmed ID: 14984738

String Representations

InChiKey (Click to copy)
KIHXTOVLSZRTHJ-ALCCZGGFSA-N
InChi (Click to copy)
InChI=1S/C12H20O3/c13-11-9-7-5-3-1-2-4-6-8-10-12(14)15/h5,7,11H,1-4,6,8-10H2,(H,14,15)/b7-5-
SMILES (Click to copy)
C(CCCCCCC/C=C\CC=O)(=O)O

Other Databases

KEGG ID
C16311
CHEBI ID
19143
PubChem CID
9548789
Cayman ID
37713

Calculated Physicochemical Properties

Heavy Atoms 15
Rings 0
Aromatic Rings 0
Rotatable Bonds 10
Van der Waals Molecular Volume 234.61
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 2.95
Molar Refractivity 59.78

Admin

Created at
-
Updated at
2nd Jan 2025