Structure Database (LMSD)

Common Name
Rumenic acid
Systematic Name
9Z,11E-octadecadienoic acid
Synonyms
  • cis-9, trans-11-octadecadienoic acid
  • bovinic acid
  • C18:2n-7,9
  • 9(Z)-11(E)-ODE
LM ID
LMFA01030118
Formula
Exact Mass
Calculate m/z
280.24023
Sum Composition
Status
Curated



Classification

Biological Context

9(Z),11(E)-Conjugated linoleic acid is an isomer of linoleic acid that has been found in beef and milk fat.1 It binds to peroxisome proliferator-activated receptor α (PPARα; IC50 = 140 nM) and activates the receptor in a reporter assay using COS-1 cells expressing mouse PPARα when used at a concentration of 100 µM.2 9(Z),11(E)-Conjugated linoleic acid inhibits TNF-α-induced GLUT4 expression and increases insulin-stimulated glucose transport in 3T3-L1 adipocytes.3 Dietary administration of 9(Z)11(E)-conjugated linoleic acid reduces serum fasting glucose, insulin, and triglyceride levels and decreases white adipose tissue macrophage infiltration in ob/ob mice. It also increases body weight gain and body fat in weanling mice.4 [Matreya, LLC. Catalog No. 1245]

This information has been provided by Cayman Chemical

References

2. Pariza, M.W., Park, Y., and Cook, M.E. The biologically active isomers of conjugated linoleic acid. Prog. Lipid Res. 40(4), 283-298 (2001).
3. Moya-Camarena, S.Y., Heuvel, J.P.V., Blanchard, S.G., et al. Conjugated linoleic acid is a potent naturally occurring ligand and activator of PPARα. J. Lipid Res. 40(8), 1426-1433 (1999).
4. Moloney, F., Toomey, S., Noone, E., et al. Antidiabetic effects of cis-9, trans-11-conjugated linoleic acid may be mediated via anti-inflammatory effects in white adipose tissue. Diabetes 56(3), 574-582 (2007).

Reactions

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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Bos taurus (#9913)
Mammalia (#40674)
Rumenic acid: a proposed common name for the major conjugated linoleic acid isomer found in natural products.,
Lipids, 1998
Pubmed ID: 9727617
Lactiplantibacillus plantarum (#1590)
Bacilli (#91061)
Production of conjugated fatty acids by lactic acid bacteria.,
J Biosci Bioeng, 2005
Pubmed ID: 16310724

String Representations

InChiKey (Click to copy)
JBYXPOFIGCOSSB-GOJKSUSPSA-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/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9-
SMILES (Click to copy)
C(/C=C\C=C\CCCCCC)CCCCCCC(=O)O

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
DFA0157
PubChem CID
SwissLipids ID
Cayman ID

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