LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Adrenic Acid

Systematic Name

7Z,10Z,13Z,16Z-docosatetraenoic acid

Synonyms

C22:4n-6,9,12,15
22:4n6

LM ID

LMFA01030178

Formula

C₂₂H₃₆O₂

Exact Mass

Calculate m/z

332.27153

Sum Composition

FA 22:4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

View ion mobility data

Classification

Biological Context

Adrenic acid is a naturally occurring polyunsaturated fatty acid (PUFA) formed through a 2-carbon chain elongation of arachidonic acid. It is present in the adrenal glands, brain, testis, and kidney.¹ Although there is trace metabolism of adrenic acid in the forebrain, the renal medulla is the only tissue which readily metabolizes the acid through cyclooxygenase activity.^1,2 The primary metabolite of adrenic acid in the rabbit kidney is 1a,1b-dihomo prostaglandin E2.1

This information has been provided by Cayman Chemical

References

1. Ferretti, A., and Flanagan, V.P. Mass spectrometric evidence for the conversion of exogenous adrenate to dihomo-prostaglandins by seminal vesicle cyclo-oxygenase. A comparative study of two animal species. J. Chromatogr. 383(2), 241-250 (1986).

2. Sprecher, H., VanRollins, M., Sun, F., et al. Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney. J. Biol. Chem. 257(7), 3912-3918 (1982).

Reactions

Filter by species:

Click on an edge to display the reaction(s).

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

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

TWSWSIQAPQLDBP-DOFZRALJSA-N

InChi (Click to copy)

InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-

SMILES (Click to copy)

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