Structure Database (LMSD)

Common Name
DHA
Systematic Name
4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid
Synonyms
  • Cervonic acid
  • Docosahexaenoic acid
  • C22:6n-3,6,9,12,15,18
LM ID
LMFA01030185
Formula
Exact Mass
Calculate m/z
328.24023
Sum Composition
Status
Curated




Classification

Biological Context

Docosahexaenoic acid (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 DHA MaxSpec® standard is a quantitative grade standard of DHA that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. The verified concentration is provided on the certificate of analysis. This DHA MaxSpec® standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.

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).

Reactions

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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

String Representations

InChiKey (Click to copy)
MBMBGCFOFBJSGT-KUBAVDMBSA-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-
SMILES (Click to copy)
C(=C/C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)/CCC(=O)O

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
DFA0224
PubChem CID
PlantFA ID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 388.26
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 6.55
Molar Refractivity 105.09

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Created at
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Updated at
25th Apr 2022