LIPID MAPS

Structure Database (LMSD)

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Common Name

22:5(4Z,7Z,10Z,13Z,16Z)

Systematic Name

4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid

Synonyms

C22:5n-6,9,12,15,18

LM ID

LMFA04000064

Formula

C₂₂H₃₄O₂

Exact Mass

Calculate m/z

330.255881

Sum Composition

FA 22:5

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

all-cis-4,7,10,13,16-DPA, also known as osbond acid, is an isomer of DPA. It is an ω-6 fatty acid formed by the elongation and desaturation of arachidonic acid . Levels of this fatty acid may be diminished during fatty acid desaturase syndrome and this may affect development.¹ Upregulated expression of hepatic elongation of very long fatty acids protein 6 and increased levels of very long chain fatty acids, including all-cis-4,7,10,13,16-DPA, are characteristic of non-alcoholic steatohepatitis, a preneoplastic condition of hepatocellular carcinoma.²

This information has been provided by Cayman Chemical

References

1. Steer, C.D., Lattka, E., Koletzko, B., et al. Maternal fatty acids in pregnancy, FADS polymorphisms, and child intelligence quotient at 8 y of age. Am. J. Clin. Nutr. 98(6), 1575-1582 (2013).

2. Muir, K., Hazim, A., He, Y., et al. Proteomic and lipidomic signatures of lipid metabolism in NASH-associated hepatocellular carcinoma. Cancer Res. 73(15), 4722-4731 (2013).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Abyssogena phaseoliformis (#1871145)

Bivalvia (#6544)

Identification of novel n-4 series polyunsaturated fatty acids in a deep-sea clam, Calyptogena phaseoliformis.,
J Chromatogr A, 2007

Pubmed ID: 17604037

String Representations

InChiKey (Click to copy)

AVKOENOBFIYBSA-WMPRHZDHSA-N

InChi (Click to copy)

InChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16,18-19H,2-5,8,11,14,17,20-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-,19-18-

SMILES (Click to copy)

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