Structure Database (LMSD)

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
330.25588
Sum Composition
FA 22:5
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Docosanoids [FA04]
Other Docosanoids [FA0400]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

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

Other Databases

HMDB ID
HMDB0001976
CHEBI ID
65136
PubChem CID
6441454
SwissLipids ID
SLM:000001208
Cayman ID
10008335

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 390.90
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 6.77
Molar Refractivity 105.18

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Updated at
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