LIPID MAPS

Structure Database (LMSD)

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Common Name

omega-3-Arachidonic acid

Systematic Name

8Z,11Z,14Z,17Z-eicosatetraenoic acid

Synonyms

C20:4n-3,6,9,12
Bishomostearidonic acid

LM ID

LMFA01030818

Formula

C₂₀H₃₂O₂

Exact Mass

Calculate m/z

304.24023

Sum Composition

FA 20:4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

ω-3 Arachidonic acid is a rare PUFA found in trace amounts in dietary sources. ω-3 Fatty acids are now known to be essential for infant growth and development and protect against heart disease, thrombosis, hypertension, and inflammatory and autoimmune disorders.¹ In human platelet membranes, ω-3 arachidonic acid inhibits arachidonoyl-CoA synthetase with a Ki of 14 µM. It also inhibits arachidonoyl-CoA synthetase in calf brain extracts with an IC50 value of about 5 µM.²

This information has been provided by Cayman Chemical

References

1. Simopoulos, A.P. Omega-3 Fatty acids in health and disease and in growth and development. Am. J. Clin. Nutr. 54(3), 438-463 (1991).

2. Neufeld, E.J., Sprecher, H., Evans, R.W., et al. Fatty acid structural requirements for activity of arachidonoyl-CoA synthetase. J. Lipid Res. 25(3), 288-293 (1984).

Reactions

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References

Reference

Medicinal and aromatic plants, Volume 8 Y. P. S. Bajaj 1995 (Springer)

String Representations

InChiKey (Click to copy)

HQPCSDADVLFHHO-LTKCOYKYSA-N

InChi (Click to copy)

InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13H,2,5,8,11,14-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-

SMILES (Click to copy)

C(CCCCCC/C=C\C/C=C\C/C=C\C/C=C\CC)(=O)O