Structure Database (LMSD)

Common Name
trans-gondoic acid
Systematic Name
11E-eicosenoic acid
Synonyms
  • trans-11-eicosenoic acid
  • trans-11-icosenoic acid
  • C20:1n-9
LM ID
LMFA01030086
Formula
C20H38O2
Exact Mass
Calculate m/z
310.28718
Sum Composition
FA 20:1
Status
Curated
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Classification

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

Biological Context

11(E)-Eicosenoic acid is a very long-chain ω-9 fatty acid that is a trans monounsaturated isomer of arachidic acid . 11(E)-Eicosenoic acid is one of several monounsaturated 20-carbon fatty acids.1 The combined C20:1 isomers constitute 70% of the total fatty acid pool in jojoba seed oil isolated from plants in the Arizona desert. Unlike other eicosenoic fatty acids, 11(E)-eicosenoic acid does not inhibit leukotriene B4 (Ki = 1,150 µM in a radioligand binding assay in pig neutrophil membranes) or affect telomerase activity.2,3

This information has been provided by Cayman Chemical

References

1. Yagaloff, K.A., Franco, L., Simko, B., et al. Essential fatty acids are antagonists of the leukotriene B4 receptor. Prostaglandins, Leukot. Essent. Fatty Acids 52(5), 293-297 (1995).
2. Miwa, T.K. Jojoba oil wax esters and derived fatty acids and alcohols: Gas chromatographic analyses. J. Am. Chem. Soc. 48(6), 259-264 (1971).
3. Eitsuka, T., Nakagawa, K., Suzuki, T., et al. Polyunsaturated fatty acids inhibit telomerase activity in DLD-1 human colorectal adenocarcinoma cells: A dual mechanism approach. Biochim. Biophys. Acta 1737(1), 1-10 (2005).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
BITHHVVYSMSWAG-MDZDMXLPSA-N
InChi (Click to copy)
InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10H,2-8,11-19H2,1H3,(H,21,22)/b10-9+
SMILES (Click to copy)
C(/C=C/CCCCCCCC)CCCCCCCCC(=O)O

Other Databases

CHEBI ID
180275
LIPIDBANK ID
DFA0125
PubChem CID
5282769
Cayman ID
22578

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 0
Aromatic Rings 0
Rotatable Bonds 17
Van der Waals Molecular Volume 366.86
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 6.89
Molar Refractivity 96.32

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Created at
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Updated at
25th Apr 2022