Arachidonic acid

(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid

Formula: C20H32O2 (304.2402)
Chinese Name: 花生四烯酸(AA), 花生四烯酸
BioDeep ID: BioDeep_00000002208 ( View LC/MS Profile)
SMILES: C(CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)C(=O)O



Found 90 Sample Hits

m/z Adducts Species Organ Scanning Sample
305.2519 [M+H]+
PPM:14.4		 Marker Pen NA DESI (None)
3ul_0.8Mpa_RAW_20241016-PAPER PNMK - MEMI_test
Resolution: 30μm, 315x42

Description

By writing the four English letters “PNMK” on white paper with a marker pen, and then scanning with a DESI ion source to obtain the scanning result. The signal of the chemical substances on the marker pen used appears on the channel with an m/z value of 322.1918, 323.1953, 546.4010, and etc, from the single cell deconvolution sampling layer class_4. This test data was tested by chuxiaoping from PANOMIX’s R&D laboratory.
305.2424 [M+H]+
PPM:16.7		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_17 - MTBLS58
Resolution: 17μm, 208x108

Description

1 male adult wild-type rat was obtained from Inserm U1085 - Irset Research Institute (University of Rennes1, France). Animals were age 60 days and were reared under ad-lib conditions. Care and handling of all animals complied with EU directive 2010/63/EU on the protection of animals used for scientific purposes. The whole epididymis was excised from each animal immediately post-mortem, loosely wrapped rapidly in an aluminum foil and a 2.5% (w/v) carboxymethylcellulose (CMC) solution was poured to embed the epididymis to preserve their morphology. To remove air bubbles, the filled aluminum molds was gently freezed by depositing it on isopentane or dry ice, then on the nitrogen vapors and finally by progressively dipping the CMC/sample coated with aluminum foil into liquid nitrogen (or only flush with liquid nitrogen). Frozen tissues were stored at -80 °C until use to avoid degradation.
269.2214 [M+H-2H2O]+
PPM:18.4		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_18 - MTBLS58
Resolution: 17μm, 208x104

Description

305.2426 [M+H]+
PPM:16		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_18 - MTBLS58
Resolution: 17μm, 208x104

Description

305.2426 [M+H]+
PPM:16		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_43 - MTBLS58
Resolution: 17μm, 298x106

Description

305.2427 [M+H]+
PPM:15.7		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_44 - MTBLS58
Resolution: 17μm, 299x111

Description

305.2429 [M+H]+
PPM:15		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_46 - MTBLS58
Resolution: 17μm, 298x106

Description

304.2611 [M-H2O+NH4]+
PPM:7.8		 Vitis vinifera Fruit MALDI (DHB)
grape_dhb_164_1 - Grape Database
Resolution: 17μm, 136x122

Description

Grape berries fruit, condition: Late
304.2612 [M-H2O+NH4]+
PPM:7.5		 Vitis vinifera Fruit MALDI (DHB)
grape_dhb_163_1 - Grape Database
Resolution: 17μm, 132x115

Description

Grape berries fruit, condition: Late
322.2749 [M+NH4]+
PPM:2.7		 Vitis vinifera Fruit MALDI (DHB)
grape_dhb_163_1 - Grape Database
Resolution: 17μm, 132x115

Description

Grape berries fruit, condition: Late
269.2218 [M+H-2H2O]+
PPM:17		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_04 - MTBLS58
Resolution: 17μm, 178x91

Description

305.2427 [M+H]+
PPM:15.7		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_04 - MTBLS58
Resolution: 17μm, 178x91

Description

269.2218 [M+H-2H2O]+
PPM:17		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_03 - MTBLS58
Resolution: 17μm, 159x110

Description

269.2217 [M+H-2H2O]+
PPM:17.3		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_06 - MTBLS58
Resolution: 17μm, 183x103

Description

305.2428 [M+H]+
PPM:15.4		 Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_14 - MTBLS58
Resolution: 17μm, 205x103

Description

322.2739 [M+NH4]+
PPM:0.4		 Posidonia oceanica root MALDI (CHCA)
MS1_20180404_PO_1200 - MTBLS1746
Resolution: 17μm, 193x208

Description

304.2368 [M]+
PPM:9.4		 Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

305.2491 [M+H]+
PPM:5.3		 Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

304.2355 [M]+
PPM:13.7		 Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

305.2478 [M+H]+
PPM:1		 Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

304.2365 [M]+
PPM:10.4		 Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

305.2487 [M+H]+
PPM:4		 Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

304.236 [M]+
PPM:12.1		 Homo sapiens esophagus DESI ()
TO42T - MTBLS385
Resolution: 17μm, 69x81

Description

305.2483 [M+H]+
PPM:2.6		 Homo sapiens esophagus DESI ()
TO42T - MTBLS385
Resolution: 17μm, 69x81

Description

304.2372 [M]+
PPM:8.1		 Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

305.2495 [M+H]+
PPM:6.6		 Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

304.2363 [M]+
PPM:11.1		 Homo sapiens esophagus DESI ()
LNTO30_8M_1 - MTBLS385
Resolution: 17μm, 69x54

Description

305.2486 [M+H]+
PPM:3.6		 Homo sapiens esophagus DESI ()
LNTO30_8M_1 - MTBLS385
Resolution: 17μm, 69x54

Description

304.2361 [M]+
PPM:11.7		 Homo sapiens esophagus DESI ()
TO39T - MTBLS385
Resolution: 17μm, 69x81

Description

305.2483 [M+H]+
PPM:2.6		 Homo sapiens esophagus DESI ()
TO39T - MTBLS385
Resolution: 17μm, 69x81

Description

304.2345 [M]+
PPM:17		 Homo sapiens colorectal adenocarcinoma DESI ()
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415
Resolution: 17μm, 137x136

Description

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).
305.2468 [M+H]+
PPM:2.3		 Homo sapiens colorectal adenocarcinoma DESI ()
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415
Resolution: 17μm, 137x136

Description

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).
304.2343 [M]+
PPM:17.6		 Homo sapiens colorectal adenocarcinoma DESI ()
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415
Resolution: 17μm, 147x131

Description

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).
305.2451 [M+H]+
PPM:7.8		 Homo sapiens colorectal adenocarcinoma DESI ()
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415
Resolution: 17μm, 147x131

Description

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).
304.2353 [M]+
PPM:14.4		 Homo sapiens colorectal adenocarcinoma DESI ()
439TopL, 409TopR, 429BottomL, 419BottomR-profile - MTBLS415
Resolution: 17μm, 157x136

Description

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).
305.2523 [M+H]+
PPM:15.7		 Homo sapiens colorectal adenocarcinoma DESI ()
439TopL, 409TopR, 429BottomL, 419BottomR-profile - MTBLS415
Resolution: 17μm, 157x136

Description

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).
304.2345 [M]+
PPM:17		 Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

305.2518 [M+H]+
PPM:14.1		 Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

327.228 [M+Na]+
PPM:4.4		 Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

304.2363 [M]+
PPM:11.1		 Homo sapiens esophagus DESI ()
LNTO29_16_3 - MTBLS385
Resolution: 17μm, 108x107

Description

305.2486 [M+H]+
PPM:3.6		 Homo sapiens esophagus DESI ()
LNTO29_16_3 - MTBLS385
Resolution: 17μm, 108x107

Description

304.2368 [M]+
PPM:9.4		 Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

305.2491 [M+H]+
PPM:5.3		 Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

304.2372 [M]+
PPM:8.1		 Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

305.2495 [M+H]+
PPM:6.6		 Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

304.2367 [M]+
PPM:9.8		 Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

305.249 [M+H]+
PPM:4.9		 Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

304.2356 [M]+
PPM:13.4		 Homo sapiens esophagus DESI ()
TO40T - MTBLS385
Resolution: 17μm, 82x74

Description

305.2479 [M+H]+
PPM:1.3		 Homo sapiens esophagus DESI ()
TO40T - MTBLS385
Resolution: 17μm, 82x74

Description

304.2364 [M]+
PPM:10.7		 Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

305.2486 [M+H]+
PPM:3.6		 Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

304.2368 [M]+
PPM:9.4		 Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

305.2491 [M+H]+
PPM:5.3		 Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

304.2363 [M]+
PPM:11.1		 Homo sapiens esophagus DESI ()
TO41T - MTBLS385
Resolution: 75μm, 69x43

Description

305.2486 [M+H]+
PPM:3.6		 Homo sapiens esophagus DESI ()
TO41T - MTBLS385
Resolution: 75μm, 69x43

Description

304.2364 [M]+
PPM:10.7		 Homo sapiens esophagus DESI ()
LNTO30_8M_2 - MTBLS385
Resolution: 75μm, 108x68

Description

305.2487 [M+H]+
PPM:4		 Homo sapiens esophagus DESI ()
LNTO30_8M_2 - MTBLS385
Resolution: 75μm, 108x68

Description

304.2364 [M]+
PPM:10.7		 Homo sapiens esophagus DESI ()
LNTO30_8M_3 - MTBLS385
Resolution: 75μm, 69x54

Description

305.2486 [M+H]+
PPM:3.6		 Homo sapiens esophagus DESI ()
LNTO30_8M_3 - MTBLS385
Resolution: 75μm, 69x54

Description

304.2366 [M]+
PPM:10.1		 Homo sapiens esophagus DESI ()
LNTO30_8M_4 - MTBLS385
Resolution: 75μm, 62x48

Description

305.2489 [M+H]+
PPM:4.6		 Homo sapiens esophagus DESI ()
LNTO30_8M_4 - MTBLS385
Resolution: 75μm, 62x48

Description

304.2365 [M]+
PPM:10.4		 Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

305.2488 [M+H]+
PPM:4.3		 Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

304.2365 [M]+
PPM:10.4		 Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

305.2487 [M+H]+
PPM:4		 Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

304.237 [M]+
PPM:8.8		 Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

305.2493 [M+H]+
PPM:5.9		 Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

304.2369 [M]+
PPM:9.1		 Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

304.2367 [M]+
PPM:9.8		 Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

305.249 [M+H]+
PPM:4.9		 Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

304.2368 [M]+
PPM:9.4		 Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

305.2491 [M+H]+
PPM:5.3		 Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

304.237 [M]+
PPM:8.8		 Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

305.2493 [M+H]+
PPM:5.9		 Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

304.2369 [M]+
PPM:9.1		 Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

305.2492 [M+H]+
PPM:5.6		 Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

304.2363 [M]+
PPM:11.1		 Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description

305.2486 [M+H]+
PPM:3.6		 Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description

304.2365 [M]+
PPM:10.4		 Homo sapiens esophagus DESI ()
LNTO30_7_1 - MTBLS385
Resolution: 75μm, 69x68

Description

305.2488 [M+H]+
PPM:4.3		 Homo sapiens esophagus DESI ()
LNTO30_7_1 - MTBLS385
Resolution: 75μm, 69x68

Description

304.2364 [M]+
PPM:10.7		 Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description

305.2486 [M+H]+
PPM:3.6		 Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description

304.2361 [M]+
PPM:11.7		 Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

305.2484 [M+H]+
PPM:3		 Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

304.2364 [M]+
PPM:10.7		 Homo sapiens colorectal adenocarcinoma DESI ()
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176
Resolution: 50μm, 132x126

Description

305.2487 [M+H]+
PPM:4		 Homo sapiens colorectal adenocarcinoma DESI ()
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176
Resolution: 50μm, 132x126

Description

304.2361 [M]+
PPM:11.7		 Homo sapiens colorectal adenocarcinoma DESI ()
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176
Resolution: 50μm, 142x136

Description

305.2484 [M+H]+
PPM:3		 Homo sapiens colorectal adenocarcinoma DESI ()
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176
Resolution: 50μm, 142x136

Description

304.2363 [M]+
PPM:11.1		 Homo sapiens colorectal adenocarcinoma DESI ()
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176
Resolution: 50μm, 132x136

Description

305.2486 [M+H]+
PPM:3.6		 Homo sapiens colorectal adenocarcinoma DESI ()
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176
Resolution: 50μm, 132x136

Description


Arachidonic acid is a polyunsaturated, essential fatty acid that has a 20-carbon chain as a backbone and four cis-double bonds at the C5, C8, C11, and C14 positions. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is synthesized from dietary linoleic acid. Arachidonic acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids. Arachidonic acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes. These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function. Arachidonic acid can be metabolized by cytochrome p450 (CYP450) enzymes into 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosatrienoic acids (DHETs), and 20-hydroxyeicosatetraenoic acid (20-HETE). The production of kidney CYP450 arachidonic acid metabolites is altered in diabetes, pregnancy, hepatorenal syndrome, and in various models of hypertension, and it is likely that changes in this system contribute to the abnormalities in renal function that are associated with many of these conditions. Phospholipase A2 (PLA2) catalyzes the hydrolysis of the sn-2 position of membrane glycerophospholipids to liberate arachidonic acid (PMID: 12736897, 12736897, 12700820, 12570747, 12432908). The beneficial effects of omega-3 fatty acids are believed to be due in part to selective alteration of arachidonate metabolism that involves cyclooxygenase (COX) enzymes (PMID: 23371504). 9-Oxononanoic acid (9-ONA), one of the major products of peroxidized fatty acids, was found to stimulate the activity of phospholipase A2 (PLA2), the key enzyme to initiate the arachidonate cascade and eicosanoid production (PMID: 23704812). Arachidonate lipoxygenase (ALOX) enzymes metabolize arachidonic acid to generate potent inflammatory mediators and play an important role in inflammation-associated diseases (PMID: 23404351). Essential fatty acid. Constituent of many animal phospholipids Arachidonic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=506-32-1 (retrieved 2024-07-15) (CAS RN: 506-32-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Arachidonic acid is an essential fatty acid and a major constituent of biomembranes. Arachidonic acid is an essential fatty acid and a major constituent of biomembranes.