Structure Database (LMSD)

Common Name
DHA (d5)
Systematic Name
4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid (d5)
Synonyms
LM ID
LMFA01030762
Formula
Exact Mass
Calculate m/z
333.271615
Status
Curated

Classification

Biological Context

Docosahexaenoic acid-d5 (DHA-d5) is intended for use as an internal standard for the quantification of DHA by GC- or LC-MS. DHA is a long-chain ω-3 polyunsaturated fatty acid (PUFA) found in fish and algal oils.1 It comprises approximately 40% of total brain PUFAs and is abundant in grey matter and retinal membranes.2 DHA typically represents 0.52-7.5% of human total plasma fatty acids. It is produced from α-linolenic acid (ALA) via a series of desaturase- and elongase-catalyzed reactions, resulting in a docosapentaenoic acid (DPA) intermediate, which is elongated, desaturated, and β-oxidized to produce DHA.3 DHA can be liberated from cellular membranes by phospholipase A2 (PLA2) and converted to numerous oxylipins, including specialized pro-resolving mediators (SPMs), which are produced by lipoxygenases and include D-series protectins and resolvins, as well as maresins, that regulate host defense and the resolution of inflammation.4 DHA has roles in several physiological and pathological processes, including neural development, cardiovascular diseases, obesity, and inflammation.3,5

This information has been provided by Cayman Chemical

References

1.Kuratko, C.N., and Salem, N., Jr. Biomarkers of DHA status. Prostaglandins Leukot. Essent. Fatty Acids 81(2-3), 111-118 (2009).
2.Lacombe, R.J.S., Chouinard-Watkins, R., and Bazinet, R.P. Brain docosahexaenoic acid uptake and metabolism. Mol. Aspects Med. 64, 109-134 (2018).
3.Calder, P.C. Docosahexaenoic acid. Ann. Nutr. Metab. 69(Suppl 1), 7-21 (2016).
4.Basil, B.C., and Levy, B.D. Specialized pro-resolving mediators: Endogenous regulators of infection and inflammation. Nat. Rev. Immunol. 16(1), 51-67 (2016).
5.Arnoldussen, I.A.C., and Kiliaan, A.J. Impact of DHA on metabolic diseases from womb to tomb. Mar. Drugs 12(12), 6190-6212 (2014).

References

Comments
Synthetic deuterated standard

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
MBMBGCFOFBJSGT-RPBOKJFVSA-N
InChi (Click to copy)
InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-/i1D3,2D2
SMILES (Click to copy)
C(=C/C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C([2H])([2H])C([2H])([2H])[2H])/CCC(=O)O

Other Databases

Wikipedia
HMDB ID
PubChem CID
Cayman ID

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Created at
-
Updated at
29th Jan 2021