Clupanodonic acid
Formula: C22H34O2 (330.2559)
Chinese Name: 二十二碳五烯酸
BioDeep ID: BioDeep_00000003493
( View LC/MS Profile)
SMILES: C(CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)(=O)O
Found 96 Sample Hits
m/z | Adducts | Species | Organ | Scanning | Sample | |
---|---|---|---|---|---|---|
330.2789 | [M-H2O+NH4]+PPM:0.7 |
Homo sapiens | Liver | MALDI (DHB) |
20171107_FIT4_DHBpos_p70_s50 - Rappez et al (2021) SpaceM reveals metabolic states of single cellsResolution: 50μm, 70x70
|
|
330.2525 | [M]+PPM:8.5 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_3 - MTBLS385Resolution: 75μm, 121x68
|
|
331.2648 | [M+H]+PPM:5 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_3 - MTBLS385Resolution: 75μm, 121x68
|
|
330.2511 | [M]+PPM:12.8 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_4 - MTBLS385Resolution: 17μm, 82x80
|
|
331.2634 | [M+H]+PPM:0.8 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_4 - MTBLS385Resolution: 17μm, 82x80
|
|
295.2473 | [M+H-2H2O]+PPM:17.9 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_2 - MTBLS385Resolution: 17μm, 95x101
|
|
313.257 | [M+H-H2O]+PPM:14.1 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_2 - MTBLS385Resolution: 17μm, 95x101
|
|
330.2522 | [M]+PPM:9.4 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_2 - MTBLS385Resolution: 17μm, 95x101
|
|
331.2644 | [M+H]+PPM:3.8 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_2 - MTBLS385Resolution: 17μm, 95x101
|
|
353.2481 | [M+Na]+PPM:8.5 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_2 - MTBLS385Resolution: 17μm, 95x101
|
|
330.2517 | [M]+PPM:11 |
Homo sapiens | esophagus | DESI () |
TO42T - MTBLS385Resolution: 17μm, 69x81
|
|
331.264 | [M+H]+PPM:2.6 |
Homo sapiens | esophagus | DESI () |
TO42T - MTBLS385Resolution: 17μm, 69x81
|
|
353.2483 | [M+Na]+PPM:9.1 |
Homo sapiens | esophagus | DESI () |
TO42T - MTBLS385Resolution: 17μm, 69x81
|
|
295.2382 | [M+H-2H2O]+PPM:12.9 |
Mus musculus | Liver | MALDI (CHCA) |
Salmonella_final_pos_recal - MTBLS2671Resolution: 17μm, 691x430
A more complete and holistic view on host–microbe interactions is needed to understand the physiological and cellular barriers that affect the efficacy of drug treatments and allow the discovery and development of new therapeutics. Here, we developed a multimodal imaging approach combining histopathology with mass spectrometry imaging (MSI) and same section imaging mass cytometry (IMC) to study the effects of Salmonella Typhimurium infection in the liver of a mouse model using the S. Typhimurium strains SL3261 and SL1344. This approach enables correlation of tissue morphology and specific cell phenotypes with molecular images of tissue metabolism. IMC revealed a marked increase in immune cell markers and localization in immune aggregates in infected tissues. A correlative computational method (network analysis) was deployed to find metabolic features associated with infection and revealed metabolic clusters of acetyl carnitines, as well as phosphatidylcholine and phosphatidylethanolamine plasmalogen species, which could be associated with pro-inflammatory immune cell types. By developing an IMC marker for the detection of Salmonella LPS, we were further able to identify and characterize those cell types which contained S. Typhimurium.
[dataset] Nicole Strittmatter. Holistic Characterization of a Salmonella Typhimurium Infection Model Using Integrated Molecular Imaging, metabolights_dataset, V1; 2022. https://www.ebi.ac.uk/metabolights/MTBLS2671. |
|
353.2449 | [M+Na]+PPM:0.5 |
Mus musculus | Liver | MALDI (CHCA) |
Salmonella_final_pos_recal - MTBLS2671Resolution: 17μm, 691x430
A more complete and holistic view on host–microbe interactions is needed to understand the physiological and cellular barriers that affect the efficacy of drug treatments and allow the discovery and development of new therapeutics. Here, we developed a multimodal imaging approach combining histopathology with mass spectrometry imaging (MSI) and same section imaging mass cytometry (IMC) to study the effects of Salmonella Typhimurium infection in the liver of a mouse model using the S. Typhimurium strains SL3261 and SL1344. This approach enables correlation of tissue morphology and specific cell phenotypes with molecular images of tissue metabolism. IMC revealed a marked increase in immune cell markers and localization in immune aggregates in infected tissues. A correlative computational method (network analysis) was deployed to find metabolic features associated with infection and revealed metabolic clusters of acetyl carnitines, as well as phosphatidylcholine and phosphatidylethanolamine plasmalogen species, which could be associated with pro-inflammatory immune cell types. By developing an IMC marker for the detection of Salmonella LPS, we were further able to identify and characterize those cell types which contained S. Typhimurium.
[dataset] Nicole Strittmatter. Holistic Characterization of a Salmonella Typhimurium Infection Model Using Integrated Molecular Imaging, metabolights_dataset, V1; 2022. https://www.ebi.ac.uk/metabolights/MTBLS2671. |
|
330.253 | [M]+PPM:7 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_9 - MTBLS385Resolution: 75μm, 89x74
|
|
331.2652 | [M+H]+PPM:6.2 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_9 - MTBLS385Resolution: 75μm, 89x74
|
|
353.2495 | [M+Na]+PPM:12.5 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_9 - MTBLS385Resolution: 75μm, 89x74
|
|
330.252 | [M]+PPM:10 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_1 - MTBLS385Resolution: 17μm, 69x54
|
|
331.2643 | [M+H]+PPM:3.5 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_1 - MTBLS385Resolution: 17μm, 69x54
|
|
330.2518 | [M]+PPM:10.7 |
Homo sapiens | esophagus | DESI () |
TO39T - MTBLS385Resolution: 17μm, 69x81
|
|
331.264 | [M+H]+PPM:2.6 |
Homo sapiens | esophagus | DESI () |
TO39T - MTBLS385Resolution: 17μm, 69x81
|
|
353.2483 | [M+Na]+PPM:9.1 |
Homo sapiens | esophagus | DESI () |
TO39T - MTBLS385Resolution: 17μm, 69x81
|
|
330.2499 | [M]+PPM:16.4 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415Resolution: 17μm, 137x136
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
|
331.2579 | [M+H]+PPM:0.4 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415Resolution: 17μm, 137x136
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
|
353.2472 | [M+Na]+PPM:6 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415Resolution: 17μm, 137x136
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
|
330.2496 | [M]+PPM:17.3 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415Resolution: 17μm, 147x131
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
|
331.2653 | [M+H]+PPM:6.5 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415Resolution: 17μm, 147x131
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
|
331.2626 | [M+H]+PPM:1.6 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
439TopL, 409TopR, 429BottomL, 419BottomR-profile - MTBLS415Resolution: 17μm, 157x136
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
|
330.2502 | [M]+PPM:15.5 |
Homo sapiens | NA | DESI () |
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415Resolution: 17μm, 142x136
|
|
331.2682 | [M+H]+PPM:15.3 |
Homo sapiens | NA | DESI () |
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415Resolution: 17μm, 142x136
|
|
295.2471 | [M+H-2H2O]+PPM:17.2 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_3 - MTBLS385Resolution: 17μm, 108x107
|
|
313.2566 | [M+H-H2O]+PPM:12.8 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_3 - MTBLS385Resolution: 17μm, 108x107
|
|
330.2519 | [M]+PPM:10.3 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_3 - MTBLS385Resolution: 17μm, 108x107
|
|
331.2642 | [M+H]+PPM:3.2 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_3 - MTBLS385Resolution: 17μm, 108x107
|
|
353.2477 | [M+Na]+PPM:7.4 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_3 - MTBLS385Resolution: 17μm, 108x107
|
|
330.2526 | [M]+PPM:8.2 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_1 - MTBLS385Resolution: 17μm, 75x74
|
|
331.2649 | [M+H]+PPM:5.3 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_1 - MTBLS385Resolution: 17μm, 75x74
|
|
353.2491 | [M+Na]+PPM:11.4 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_1 - MTBLS385Resolution: 17μm, 75x74
|
|
330.253 | [M]+PPM:7 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_2 - MTBLS385Resolution: 17μm, 135x101
|
|
331.2653 | [M+H]+PPM:6.5 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_2 - MTBLS385Resolution: 17μm, 135x101
|
|
330.2524 | [M]+PPM:8.8 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_3 - MTBLS385Resolution: 75μm, 82x88
|
|
331.2647 | [M+H]+PPM:4.7 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_3 - MTBLS385Resolution: 75μm, 82x88
|
|
353.249 | [M+Na]+PPM:11.1 |
Homo sapiens | esophagus | DESI () |
LNTO26_7_3 - MTBLS385Resolution: 75μm, 82x88
|
|
331.2635 | [M+H]+PPM:1.1 |
Homo sapiens | esophagus | DESI () |
TO40T - MTBLS385Resolution: 17μm, 82x74
|
|
353.2476 | [M+Na]+PPM:7.1 |
Homo sapiens | esophagus | DESI () |
TO40T - MTBLS385Resolution: 17μm, 82x74
|
|
330.252 | [M]+PPM:10 |
Homo sapiens | esophagus | DESI () |
TO31T - MTBLS385Resolution: 75μm, 56x54
|
|
331.2643 | [M+H]+PPM:3.5 |
Homo sapiens | esophagus | DESI () |
TO31T - MTBLS385Resolution: 75μm, 56x54
|
|
353.2486 | [M+Na]+PPM:9.9 |
Homo sapiens | esophagus | DESI () |
TO31T - MTBLS385Resolution: 75μm, 56x54
|
|
330.2525 | [M]+PPM:8.5 |
Homo sapiens | esophagus | DESI () |
TO29T - MTBLS385Resolution: 75μm, 56x48
|
|
331.2648 | [M+H]+PPM:5 |
Homo sapiens | esophagus | DESI () |
TO29T - MTBLS385Resolution: 75μm, 56x48
|
|
353.2491 | [M+Na]+PPM:11.4 |
Homo sapiens | esophagus | DESI () |
TO29T - MTBLS385Resolution: 75μm, 56x48
|
|
330.2519 | [M]+PPM:10.3 |
Homo sapiens | esophagus | DESI () |
TO41T - MTBLS385Resolution: 75μm, 69x43
|
|
331.2643 | [M+H]+PPM:3.5 |
Homo sapiens | esophagus | DESI () |
TO41T - MTBLS385Resolution: 75μm, 69x43
|
|
330.2521 | [M]+PPM:9.7 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_2 - MTBLS385Resolution: 75μm, 108x68
|
|
331.2644 | [M+H]+PPM:3.8 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_2 - MTBLS385Resolution: 75μm, 108x68
|
|
330.252 | [M]+PPM:10 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_3 - MTBLS385Resolution: 75μm, 69x54
|
|
331.2643 | [M+H]+PPM:3.5 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_3 - MTBLS385Resolution: 75μm, 69x54
|
|
330.2523 | [M]+PPM:9.1 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_4 - MTBLS385Resolution: 75μm, 62x48
|
|
331.2646 | [M+H]+PPM:4.4 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_4 - MTBLS385Resolution: 75μm, 62x48
|
|
330.2523 | [M]+PPM:9.1 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_5 - MTBLS385Resolution: 75μm, 56x54
|
|
331.2645 | [M+H]+PPM:4.1 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_5 - MTBLS385Resolution: 75μm, 56x54
|
|
353.2483 | [M+Na]+PPM:9.1 |
Homo sapiens | esophagus | DESI () |
LNTO30_8M_5 - MTBLS385Resolution: 75μm, 56x54
|
|
330.2521 | [M]+PPM:9.7 |
Homo sapiens | esophagus | DESI () |
LNTO30_17_2 - MTBLS385Resolution: 75μm, 82x54
|
|
331.2644 | [M+H]+PPM:3.8 |
Homo sapiens | esophagus | DESI () |
LNTO30_17_2 - MTBLS385Resolution: 75μm, 82x54
|
|
330.2527 | [M]+PPM:7.9 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_5 - MTBLS385Resolution: 75μm, 135x94
|
|
331.2651 | [M+H]+PPM:5.9 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_5 - MTBLS385Resolution: 75μm, 135x94
|
|
330.2526 | [M]+PPM:8.2 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_7 - MTBLS385Resolution: 75μm, 69x54
|
|
331.2649 | [M+H]+PPM:5.3 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_7 - MTBLS385Resolution: 75μm, 69x54
|
|
353.2491 | [M+Na]+PPM:11.4 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_7 - MTBLS385Resolution: 75μm, 69x54
|
|
330.2524 | [M]+PPM:8.8 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_8 - MTBLS385Resolution: 75μm, 69x61
|
|
331.2647 | [M+H]+PPM:4.7 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_8 - MTBLS385Resolution: 75μm, 69x61
|
|
330.2525 | [M]+PPM:8.5 |
Homo sapiens | esophagus | DESI () |
LNTO22_2_1 - MTBLS385Resolution: 75μm, 89x88
|
|
331.2648 | [M+H]+PPM:5 |
Homo sapiens | esophagus | DESI () |
LNTO22_2_1 - MTBLS385Resolution: 75μm, 89x88
|
|
330.2527 | [M]+PPM:7.9 |
Homo sapiens | esophagus | DESI () |
LNTO22_2_2 - MTBLS385Resolution: 75μm, 135x94
|
|
331.265 | [M+H]+PPM:5.6 |
Homo sapiens | esophagus | DESI () |
LNTO22_2_2 - MTBLS385Resolution: 75μm, 135x94
|
|
330.2526 | [M]+PPM:8.2 |
Homo sapiens | esophagus | DESI () |
LNTO26_16_1 - MTBLS385Resolution: 75μm, 95x88
|
|
331.2649 | [M+H]+PPM:5.3 |
Homo sapiens | esophagus | DESI () |
LNTO26_16_1 - MTBLS385Resolution: 75μm, 95x88
|
|
353.2491 | [M+Na]+PPM:11.4 |
Homo sapiens | esophagus | DESI () |
LNTO26_16_1 - MTBLS385Resolution: 75μm, 95x88
|
|
295.2473 | [M+H-2H2O]+PPM:17.9 |
Homo sapiens | esophagus | DESI () |
LNTO29_18_2 - MTBLS385Resolution: 75μm, 62x68
|
|
330.2519 | [M]+PPM:10.3 |
Homo sapiens | esophagus | DESI () |
LNTO29_18_2 - MTBLS385Resolution: 75μm, 62x68
|
|
331.2642 | [M+H]+PPM:3.2 |
Homo sapiens | esophagus | DESI () |
LNTO29_18_2 - MTBLS385Resolution: 75μm, 62x68
|
|
353.2478 | [M+Na]+PPM:7.7 |
Homo sapiens | esophagus | DESI () |
LNTO29_18_2 - MTBLS385Resolution: 75μm, 62x68
|
|
330.2522 | [M]+PPM:9.4 |
Homo sapiens | esophagus | DESI () |
LNTO30_7_1 - MTBLS385Resolution: 75μm, 69x68
|
|
331.2644 | [M+H]+PPM:3.8 |
Homo sapiens | esophagus | DESI () |
LNTO30_7_1 - MTBLS385Resolution: 75μm, 69x68
|
|
330.252 | [M]+PPM:10 |
Homo sapiens | esophagus | DESI () |
LNTO30_7_2 - MTBLS385Resolution: 75μm, 82x68
|
|
331.2643 | [M+H]+PPM:3.5 |
Homo sapiens | esophagus | DESI () |
LNTO30_7_2 - MTBLS385Resolution: 75μm, 82x68
|
|
330.2518 | [M]+PPM:10.7 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176Resolution: 50μm, 142x141
|
|
331.2641 | [M+H]+PPM:2.9 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176Resolution: 50μm, 142x141
|
|
330.2521 | [M]+PPM:9.7 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176Resolution: 50μm, 132x126
|
|
331.2644 | [M+H]+PPM:3.8 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176Resolution: 50μm, 132x126
|
|
330.2517 | [M]+PPM:11 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176Resolution: 50μm, 142x136
|
|
331.264 | [M+H]+PPM:2.6 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176Resolution: 50μm, 142x136
|
|
330.252 | [M]+PPM:10 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176Resolution: 50μm, 132x136
|
|
331.2642 | [M+H]+PPM:3.2 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176Resolution: 50μm, 132x136
|
|
353.2484 | [M+Na]+PPM:9.4 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176Resolution: 50μm, 132x136
|
|
Docosapentaenoic acid (also known as clupanodonic acid) is an essential omega-3 fatty acid (EFA) which is prevalent in fish oils. Docosapentaenoic acid, commonly called DPA, is an intermediary between eicosapentaenoic acid (EPA, 20:5 ω-3) and docosahexaenoic acid (DHA, 22:6 ω-3). Seal oil is a rich source. There are three functions of docosapentaenoic acid. The most important is as part of phospholipids in all animal cellular membranes: a deficiency of docosapentaenoic acid leads to faulty membranes being formed. A second is in the transport and oxidation of cholesterol: clupanodonic acid tends to lower plasma cholesterol. A third function is as a precursor of prostanoids which are only formed from docosapentaenoic acid. Deficiency of this in experimental animals causes lesions mainly attributable to faulty cellular membranes: sudden failure of growth, lesions of skin and kidney and connective tissue, erythrocyte fragility, impaired fertility, uncoupling of oxidation and phosphorylation. In man pure deficiency of docosapentaenoic acid has been studied particularly in persons fed intravenously. A relative deficiency (that is, a low ratio in the body of docosapentaenoic to long-chain saturated fatty acids and isomers of docosapentaenoate) is common on Western diets and plays an important part in the causation of atherosclerosis, coronary thrombosis, multiple sclerosis, the triopathy of diabetes mellitus, hypertension and certain forms of malignant disease. Various factors affect the dietary requirement of docosapentaenoic acid. (PMID: 6469703) [HMDB]. 7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid is found in many foods, some of which are green zucchini, green bell pepper, green bean, and red bell pepper. Docosapentaenoic acid (22n-3) (also known as clupanodonic acid) is an essential omega-3 fatty acid (EFA) which is prevalent in fish oils. Docosapentaenoic acid, commonly called DPA, is an intermediary between eicosapentaenoic acid (EPA, 20:5 ω-3) and docosahexaenoic acid (DHA, 22:6 ω-3). Seal oil is a rich source of this metabolite. There are three functions of docosapentaenoic acid. Most importantly, it is a component of phospholipids found in all animal cell membranes, and a deficiency of docosapentaenoic acid leads to faulty membranes being formed. Secondly, it is involved in the transport and oxidation of cholesterol, and clupanodonic acid tends to lower plasma cholesterol. A third function is as a precursor of prostanoids which are only formed from docosapentaenoic acid. Deficiency of this in experimental animals causes lesions mainly attributable to faulty cellular membranes. Outcomes include sudden failure of growth, lesions of the skin, kidney, and connective tissue, erythrocyte fragility, impaired fertility, and the uncoupling of oxidation and phosphorylation. In humans, pure deficiency of docosapentaenoic acid has been studied particularly in persons fed intravenously. A relative deficiency (that is, a low ratio in the body of docosapentaenoic to long-chain saturated fatty acids and isomers of docosapentaenoate) is common in Western diets and plays an important part in the causation of atherosclerosis, coronary thrombosis, multiple sclerosis, the triopathy of diabetes mellitus, hypertension, and certain forms of malignant disease. Various factors affect the dietary requirement of docosapentaenoic acid (PMID: 6469703). Docosapentaenoic acid (22n-3) is a component of phospholipids found in all animal cell membranes.