Structure Database (LMSD)

Common Name
10E,12Z-octadecadienoic acid
Systematic Name
10E,12Z-octadecadienoic acid
Synonyms
  • trans-10, cis-12-octadecadienoic acid
  • C18:2n-6,8
  • 10(E),12(Z)-ODE
LM ID
LMFA01030125
Formula
C18H32O2
Exact Mass
Calculate m/z
280.240231
Sum Composition
FA 18:2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Octadecanoids [FA02]

Biological Context

10(E),12(Z)-Conjugated linoleic acid is an isomer of linoleic acid that has been found in bovine milk products.1 It binds to peroxisome proliferator-activated receptor α (PPARα; IC50 = 200 nM) and activates PPARα in a reporter assay using COS-1 cells expressing the mouse receptor.2 10(E),12(Z)-Conjugated linoleic acid also inhibits stearoyl-CoA desaturase activity in mouse liver microsomes and tartrate-resistant acid phosphatase (TRAP) activity in media from primary human CD14+ monocytes.3,4 It induces apoptosis in LoVo and HT-29 colon cancer cells when used at a concentration of 100 µM.5 10(E),12(Z)-Conjugated linoleic acid reduces epididymal, perirenal, and subcutaneous white adipose tissue weights in hamsters fed an atherogenic diet.6

This information has been provided by Cayman Chemical

References

1. Houseknecht, K.L., Vanden Heuvel, J.P., Moya-Camarena, S.Y., et al. Dietary conjugated linoleic acid normalizes impaired glucose tolerance in the Zucker diabetic fatty fa/fa rat. Biochem. Biophys. Res. Commun. 244(3), 678-682 (1998).
2. Shultz, T.D., Chew, B.P., Seaman, W.R., et al. Inhibitory effect of conjugated dienoic derivatives of linoleic acid and β-carotene on the in vitro growth of human cancer cells. Cancer Lett. 63(2), 125-133 (1992).

Reactions

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References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Lactiplantibacillus plantarum (#1590)
Bacilli (#91061)
Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition.,
Proc Natl Acad Sci U S A, 2013
Pubmed ID: 24127592

String Representations

InChiKey (Click to copy)
GKJZMAHZJGSBKD-NMMTYZSQSA-N
InChi (Click to copy)
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-9H,2-5,10-17H2,1H3,(H,19,20)/b7-6-,9-8+
SMILES (Click to copy)
C(=C/C=C\CCCCC)\CCCCCCCCC(=O)O

Other Databases

CHEBI ID
44526
LIPIDBANK ID
DFA0164
PubChem CID
5282800
PlantFA ID
10783
Cayman ID
90145
PDB ID
ODD

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 329.62
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.88
Molar Refractivity 86.99

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Created at
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Updated at
5th Jan 2023