LIPID MAPS

Structure Database (LMSD)

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Common Name

32:6(14Z,17Z,20Z,23Z,26Z,29Z)

Systematic Name

14Z,17Z,20Z,23Z,26Z,29Z-dotriacontahexaenoic acid

Synonyms

32:6(w3)
32:6n3

LM ID

LMFA01030841

Formula

C₃₂H₅₂O₂

Exact Mass

Calculate m/z

468.396731

Sum Composition

FA 32:6

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Very long chain polyunsaturated fatty acids (VLCPUFA) are present in retina, sperm, and brain.^1,2,3 Though little is known of their biosynthesis or functional roles in these tissues, recent studies using the elongation of very long-chain FA-4 protein suggest a unique role for VLCPUFA in retinal development and macular degeneration.^4,5 CAY10632 is a C32:6 VLCPUFA whose specific biological actions are largely unknown, but are thought to involve normal photoreceptor cell function in the retina.^4,6

This information has been provided by Cayman Chemical

References

1. Robinson, B.S., Johnson, D.W., and Poulos, A. Novel molecular species of spingomyelin containing 2-hydroxylated polyenoic very-long-chain fatty acids in mammalian testes and spermatozoa. The Journal of Biological Chemisty 267(3), 1746-1751 (1992).

2. McMahon, A., Jackson, S.N., Woods, A.S., et al. A Stargardt disease-3 mutation in the mouse Elovl4 gene causes retinal deficiency of C32-C36 acyl phosphatidylcholines. FEBS Lett. 581(28), 5459-5463 (2007).

3. Agbaga, M.P., Mandal, M.N.A., and Anderson, R.E. Retinal very long-chain PUFAs: New insights from studies on ELOVL4 protein. J. Lipid Res. 51(7), 1624-1642 (2010).

4. Aveldaño, M.I. Phospholipid species containing long and very long polyenoic fatty acids remain with rhodopsin after hexane extraction of photoreceptor membranes. Biochemistry 27(4), 1229-1239 (1988).

5. Robinson, B.S., Johnson, D.W., and Poulos, A. Unique molecular species of phophatidylcholine containing very-long-chain (C24-C38) polyenoic fatty acids in rat brain. Biochem. J. 265(3), 763-767 (1990).

6. Agbada, M.P., Brush, R.S., Mandal, N.A., et al. Role of Stargardt-3 macular dystrophy protein (ELOVL4) in the biosynthesis of very long chain fatty acids. Proc. Natl. Acad. Sci. USA 105(35), 12843-12848 (2008).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Long-chain and very long-chain polyunsaturated fatty acids in ocular aging and age-related macular degeneration,
J. Lipid Res, 2010

Pubmed ID: 20688753

DOI: 10.1194/jlr.M007518

String Representations

InChiKey (Click to copy)

HIKGLCYKBLODNY-KUBAVDMBSA-N

InChi (Click to copy)

InChI=1S/C32H52O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-32(33)34/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-31H2,1H3,(H,33,34)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

SMILES (Click to copy)

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