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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (113)transporters (2) Show 115 proteins XML

enzymes (113)transporters (2) Show 115 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001043

Secondary Accession Numbers

HMDB0060102
HMDB01043
HMDB60102

Metabolite Identification

Common Name

Arachidonic acid

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 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0001043
     RDKit          3D
Arachidonic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    7.3727    1.2639   -0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0664    0.6156   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9514    1.5387   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    1.0743   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382    0.7661    1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260   -0.3409    1.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0148   -1.3744    2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991   -1.6286    1.8723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433   -2.8985    1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823   -3.1489    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2099   -2.2849   -0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1113   -0.8682   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9997   -0.1831   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -0.7727   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690   -0.4501    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0505    0.2643    0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7583    0.8001   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1590    0.2093   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9938    0.6645   -1.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2366    2.0972   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8528    2.5457   -2.4835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8675    3.0291   -0.5058 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0494    0.4283   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7379    1.9904   -0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0705    1.7923   -1.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9666   -0.4013   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2177    0.5977    0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407    2.5388   -0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179    1.8369   -1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3588    0.1150   -0.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8288    1.7895   -0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841    1.7426    1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0224    0.7851    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7914   -0.2886    2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5742   -2.1618    2.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1788   -1.8582    2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9727   -0.8004    1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8955   -3.7725    1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102   -4.2430   -0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -2.4850   -1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887   -2.7196   -1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539   -0.2861   -0.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834    0.9088   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388   -1.9022   -0.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9147   -0.4595   -1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496   -0.8428    1.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4643    0.4857    1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9475    1.9090   -0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2753    0.8090   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6198    0.5752    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1324   -0.8902   -0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4721    0.3477   -2.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9708    0.1143   -1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5346    3.4263    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 22 54  1  0
M  END


  Mrv1652303231821242D          

 22 21  0  0  0  0            999 V2000
   -1.2343    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4129    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6587    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6230   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3332    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0474   -0.2808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3332    0.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2258   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9359    0.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6501   -0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001043

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
YZXBAPSDXZZRGB-DOFZRALJSA-N

> <FORMULA>
C20H32O2

> <MOLECULAR_WEIGHT>
304.4669

> <EXACT_MASS>
304.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.19605148359834

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.80

> <JCHEM_LOGP>
6.587170811

> <ALOGPS_LOGS>
-6.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840522258

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
99.95399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arachidonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001043
     RDKit          3D
Arachidonic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    7.3727    1.2639   -0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0664    0.6156   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9514    1.5387   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    1.0743   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382    0.7661    1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260   -0.3409    1.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0148   -1.3744    2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991   -1.6286    1.8723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433   -2.8985    1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823   -3.1489    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2099   -2.2849   -0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1113   -0.8682   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9997   -0.1831   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -0.7727   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690   -0.4501    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0505    0.2643    0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7583    0.8001   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1590    0.2093   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9938    0.6645   -1.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2366    2.0972   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8528    2.5457   -2.4835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8675    3.0291   -0.5058 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0494    0.4283   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7379    1.9904   -0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0705    1.7923   -1.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9666   -0.4013   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2177    0.5977    0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407    2.5388   -0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179    1.8369   -1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3588    0.1150   -0.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8288    1.7895   -0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841    1.7426    1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0224    0.7851    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7914   -0.2886    2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5742   -2.1618    2.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1788   -1.8582    2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9727   -0.8004    1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8955   -3.7725    1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102   -4.2430   -0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -2.4850   -1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887   -2.7196   -1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539   -0.2861   -0.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834    0.9088   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388   -1.9022   -0.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9147   -0.4595   -1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496   -0.8428    1.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4643    0.4857    1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9475    1.9090   -0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2753    0.8090   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6198    0.5752    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1324   -0.8902   -0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4721    0.3477   -2.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9708    0.1143   -1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5346    3.4263    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 22 54  1  0
M  END

HEADER    PROTEIN                                 23-MAR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-18         0                                  
HETATM    1  C   UNK     0      -2.304   0.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.771   0.247   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.638  -0.524   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.563  -0.524   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.963   0.247   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.896   0.247   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.504   0.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.429   0.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.822  -0.524   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.762  -0.524   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.163   0.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.088   0.247   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.496  -0.524   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.629   0.247   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -11.822   0.247   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.963  -0.524   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -13.155  -0.524   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0     -11.822   1.780   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.288   0.247   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.622  -0.524   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.947   0.247   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.280  -0.524   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17   18                                                  
CONECT   16   14   19                                                       
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0001043
HETATM    1  C1  UNL     1       7.373   1.264  -0.879  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.066   0.616  -0.328  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.951   1.539  -0.669  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.609   1.074  -0.337  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.138   0.766   1.016  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.726  -0.341   1.740  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.015  -1.374   2.100  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.599  -1.629   1.872  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.443  -2.899   1.159  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.882  -3.149   0.038  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.210  -2.285  -0.913  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.111  -0.868  -0.697  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.000  -0.183  -0.533  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.383  -0.773  -0.541  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.969  -0.450   0.767  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.050   0.264   0.904  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.758   0.800  -0.259  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.159   0.209  -0.249  1.00  0.00           C  
HETATM   19  C19 UNL     1      -6.994   0.665  -1.392  1.00  0.00           C  
HETATM   20  C20 UNL     1      -7.237   2.097  -1.454  1.00  0.00           C  
HETATM   21  O1  UNL     1      -7.853   2.546  -2.483  1.00  0.00           O  
HETATM   22  O2  UNL     1      -6.868   3.029  -0.506  1.00  0.00           O  
HETATM   23  H1  UNL     1       8.049   0.428  -1.062  1.00  0.00           H  
HETATM   24  H2  UNL     1       7.738   1.990  -0.142  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.070   1.792  -1.799  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.967  -0.401  -0.676  1.00  0.00           H  
HETATM   27  H5  UNL     1       6.218   0.598   0.796  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.141   2.539  -0.158  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.018   1.837  -1.779  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.359   0.115  -0.961  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.829   1.790  -0.786  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.384   1.743   1.644  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.022   0.785   1.035  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.791  -0.289   2.016  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.574  -2.162   2.656  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.179  -1.858   2.931  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.973  -0.800   1.562  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.896  -3.772   1.699  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.910  -4.243  -0.278  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.766  -2.485  -1.920  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.789  -2.720  -1.161  1.00  0.00           H  
HETATM   42  H20 UNL     1       1.054  -0.286  -0.704  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.883   0.909  -0.379  1.00  0.00           H  
HETATM   44  H22 UNL     1      -2.339  -1.902  -0.626  1.00  0.00           H  
HETATM   45  H23 UNL     1      -2.915  -0.460  -1.429  1.00  0.00           H  
HETATM   46  H24 UNL     1      -2.450  -0.843   1.642  1.00  0.00           H  
HETATM   47  H25 UNL     1      -4.464   0.486   1.923  1.00  0.00           H  
HETATM   48  H26 UNL     1      -4.948   1.909  -0.034  1.00  0.00           H  
HETATM   49  H27 UNL     1      -4.275   0.809  -1.215  1.00  0.00           H  
HETATM   50  H28 UNL     1      -6.620   0.575   0.716  1.00  0.00           H  
HETATM   51  H29 UNL     1      -6.132  -0.890  -0.142  1.00  0.00           H  
HETATM   52  H30 UNL     1      -6.472   0.348  -2.329  1.00  0.00           H  
HETATM   53  H31 UNL     1      -7.971   0.114  -1.376  1.00  0.00           H  
HETATM   54  H32 UNL     1      -7.535   3.426   0.138  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7    7   34
CONECT    7    8   35
CONECT    8    9   36   37
CONECT    9   10   10   38
CONECT   10   11   39
CONECT   11   12   40   41
CONECT   12   13   13   42
CONECT   13   14   43
CONECT   14   15   44   45
CONECT   15   16   16   46
CONECT   16   17   47
CONECT   17   18   48   49
CONECT   18   19   50   51
CONECT   19   20   52   53
CONECT   20   21   21   22
CONECT   22   54
END

HMDB0001043
     RDKit          3D
Arachidonic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    7.3727    1.2639   -0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0664    0.6156   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9514    1.5387   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    1.0743   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382    0.7661    1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260   -0.3409    1.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0148   -1.3744    2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991   -1.6286    1.8723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433   -2.8985    1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823   -3.1489    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2099   -2.2849   -0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1113   -0.8682   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9997   -0.1831   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -0.7727   -0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690   -0.4501    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0505    0.2643    0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7583    0.8001   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1590    0.2093   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9938    0.6645   -1.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2366    2.0972   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8528    2.5457   -2.4835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8675    3.0291   -0.5058 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0494    0.4283   -1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7379    1.9904   -0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0705    1.7923   -1.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9666   -0.4013   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2177    0.5977    0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407    2.5388   -0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179    1.8369   -1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3588    0.1150   -0.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8288    1.7895   -0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841    1.7426    1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0224    0.7851    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7914   -0.2886    2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5742   -2.1618    2.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1788   -1.8582    2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9727   -0.8004    1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8955   -3.7725    1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102   -4.2430   -0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -2.4850   -1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887   -2.7196   -1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539   -0.2861   -0.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834    0.9088   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388   -1.9022   -0.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9147   -0.4595   -1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496   -0.8428    1.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4643    0.4857    1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9475    1.9090   -0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2753    0.8090   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6198    0.5752    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1324   -0.8902   -0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4721    0.3477   -2.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9708    0.1143   -1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5346    3.4263    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 22 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid	ChEBI
(5Z,8Z,11Z,14Z)-Icosatetraenoic acid	ChEBI
AA	ChEBI
all-cis-5,8,11,14-Eicosatetraenoic acid	ChEBI
ARA	ChEBI
Arachidonate	ChEBI
Arachidonsaeure	ChEBI
cis-5,8,11,14-Eicosatetraenoic acid	ChEBI
cis-Delta(5,8,11,14)-Eicosatetraenoic acid	ChEBI
5Z,8Z,11Z,14Z-Eicosatetraenoic acid	Kegg
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid	Kegg
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoate	Generator
(5Z,8Z,11Z,14Z)-Icosatetraenoate	Generator
all-cis-5,8,11,14-Eicosatetraenoate	Generator
cis-5,8,11,14-Eicosatetraenoate	Generator
cis-delta(5,8,11,14)-Eicosatetraenoate	Generator
cis-Δ(5,8,11,14)-eicosatetraenoate	Generator
cis-Δ(5,8,11,14)-eicosatetraenoic acid	Generator
5Z,8Z,11Z,14Z-Eicosatetraenoate	Generator
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoate	Generator
(all-Z)-5,8,11,14-Eicosatetraenoate	HMDB
(all-Z)-5,8,11,14-Eicosatetraenoic acid	HMDB
5,8,11,14-all-cis-Eicosatetraenoate	HMDB
5,8,11,14-all-cis-Eicosatetraenoic acid	HMDB
5,8,11,14-Eicosatetraenoate	HMDB
5,8,11,14-Eicosatetraenoic acid	HMDB
5-cis,8-cis,11-cis,14-cis-Eicosatetraenoate	HMDB
5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acid	HMDB
cis-D5,8,11,14-Eicosatetraenoate	HMDB
cis-D5,8,11,14-Eicosatetraenoic acid	HMDB
Immunocytophyte	HMDB
Arachidonate, sodium	HMDB
Arachidonic acid, (all-Z)-isomer, 3H-labeled	HMDB
Arachidonic acid, ammonium salt, (all-Z)-isomer	HMDB
Arachidonic acid, cerium salt, (all-Z)-isomer	HMDB
Arachidonic acid, sodium salt	HMDB
Arachidonic acid, sodium salt, (all-Z)-isomer	HMDB
Vitamin F	HMDB
Arachidonic acid, cesium salt, (all-Z)-isomer	HMDB
Arachidonic acid, lithium salt, (all-Z)-isomer	HMDB
Arachidonic acid, potassium salt, (all-Z)-isomer	HMDB
Sodium arachidonate	HMDB
Arachidonic acid, (all-Z)-isomer, 1-(14)C-labeled	HMDB
Arachidonic acid, zinc salt, (all-Z)-isomer	HMDB
FA(20:4(5Z,8Z,11Z,14Z))	HMDB
FA(20:4n6)	HMDB

Chemical Formula

C₂₀H₃₂O₂

Average Molecular Weight

304.4669

Monoisotopic Molecular Weight

304.240230268

IUPAC Name

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

Traditional Name

arachidonic acid

CAS Registry Number

506-32-1

SMILES

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

InChI Identifier

InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

InChI Key

YZXBAPSDXZZRGB-DOFZRALJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:15843 )
omega-6 fatty acid (CHEBI:15843 )
icosa-5,8,11,14-tetraenoic acid (CHEBI:15843 )
Unsaturated fatty acids (C00219 )
Polyunsaturated fatty acids (C00219 )
Unsaturated fatty acids (LMFA01030001 )

Ontology

Physiological effect

Health effect

Schizophrenia (HMDB: HMDB0001043)
Essential hypertension (HMDB: HMDB0001043)
Gestational diabetes (HMDB: HMDB0001043)

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0001043)

Disposition

Biological location

Biofluid or Excreta

Cerebrospinal fluid (HMDB: HMDB0001043)

Non-excretory biofluid

Cerebrospinal Fluid (CSF) (PMID: 2835791)
Blood (PMID: 14634727)
Saliva (PMID: 24421258)

Excreta

Urine (PMID: 14643447)
Feces (PMID: 19636438)

Cellular element

Platelet (HMDB: HMDB0001043)

Tissue substructure

Cell

Hematocyte

Platelet (HMDB: HMDB0001043)

Fibroblast

Fibroblast (HMDB: HMDB0001043)

Organ

Gland

Endocrine gland

Thyroid gland (HMDB: HMDB0001043)

Thyroid Gland (HMDB: HMDB0001043)

Tissue

Nervous tissue

Nervous tissue (HMDB: HMDB0001043)

Connective tissue

Adipose Tissue (HMDB: HMDB0001043)

Epithelium

Epidermis (HMDB: HMDB0001043)

Muscle tissue

Skeletal Muscle (HMDB: HMDB0001043)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0001043)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001043)

Source

Endogenous

Endogenous (HMDB: HMDB0001043)

Plant

Animal

Animal (HMDB: HMDB0001043)

Exogenous

Food

Food (HMDB: HMDB0001043)

Animal origin

Poultry

Chicken (FooDB: FOOD00329)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Lagomorph

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Oilseed crop

Aquatic origin

Fish

Anchovy (FooDB: FOOD00566)
Blue whiting (FooDB: FOOD00567)
Carp bream (FooDB: FOOD00568)
Clupeinae (Herring, Sardine, Sprat) (FooDB: FOOD00520)
Burbot (FooDB: FOOD00313)
Sturgeon (FooDB: FOOD00570)
Charr (FooDB: FOOD00571)
Gadus (Common cod) (FooDB: FOOD00515)
Common dab (FooDB: FOOD00574)
Spiny dogfish (FooDB: FOOD00575)
Anguilliformes (FooDB: FOOD00577)
Flatfish (FooDB: FOOD00535)
Garfish (FooDB: FOOD00579)
Haddock (FooDB: FOOD00374)
Gadiformes (FooDB: FOOD00580)
Atlantic halibut (FooDB: FOOD00516)
Greenland halibut/turbot (FooDB: FOOD00370)
Lake trout (FooDB: FOOD00582)
Lemon sole (FooDB: FOOD00583)
Common ling (FooDB: FOOD00397)
Lumpsucker (FooDB: FOOD00585)
Scombridae (Bonito, Mackerel, Tuna) (FooDB: FOOD00586)
Norway haddock (FooDB: FOOD00588)
Norway pout (FooDB: FOOD00590)
Perciformes (FooDB: FOOD00527)
Northern pike (FooDB: FOOD00431)
Pikeperch (FooDB: FOOD00595)
Pleuronectidae (Dab, Halibut, Plaice) (FooDB: FOOD00596)
Pollock (FooDB: FOOD00513)
Rainbow trout (FooDB: FOOD00444)
Pacific ocean perch (FooDB: FOOD00598)
Salmonidae (Salmon, Trout) (FooDB: FOOD00493)
True sole (FooDB: FOOD00604)
Catfish (FooDB: FOOD00605)
Thunnus (FooDB: FOOD00607)
Turbot (FooDB: FOOD00364)
Whitefish (FooDB: FOOD00503)
Whiting (FooDB: FOOD00504)
Atlantic wolffish (FooDB: FOOD00296)
Coho salmon (FooDB: FOOD00452)

Crustacean

Fish product

Other fish product (FooDB: FOOD00665)

Amphibian

True frog (FooDB: FOOD00578)

Mollusk

Pinniped

True seal (FooDB: FOOD00600)

Seaweed

Red algae (FooDB: FOOD00601)
Kombu (FooDB: FOOD00602)
Agar (FooDB: FOOD00284)

Cetacean

Cetacea (Dolphin, Porpoise, Whale) (FooDB: FOOD00609)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Fruit product

Other fruit product (FooDB: FOOD00765)
Fruit preserve (FooDB: FOOD00660)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)

Other vegetable

Okra (FooDB: FOOD00420)

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Beverage

Distilled beverage

Spirit (FooDB: FOOD00276)
Gin (FooDB: FOOD00625)
Liquor (FooDB: FOOD00616)
Rum (FooDB: FOOD00629)
Vodka (FooDB: FOOD00622)
Whisky (FooDB: FOOD00623)

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Other beverage

Fortified wines

Water

Water (FooDB: FOOD00664)

Alcoholic beverage

Other alcoholic beverage (FooDB: FOOD00278)

Baby food

Baby food (FooDB: FOOD00668)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Chickpea (FooDB: FOOD00047)
Common pea (FooDB: FOOD00141)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Leavened bread

Wheat bread (FooDB: FOOD00808)
Rye bread (FooDB: FOOD00809)

Cereal

Barley (FooDB: FOOD00088)
Common buckwheat (FooDB: FOOD00079)
Corn (FooDB: FOOD00205)
Millet (FooDB: FOOD00126)
Oat (FooDB: FOOD00022)
Rice (FooDB: FOOD00125)
Rye (FooDB: FOOD00169)
Wheat (FooDB: FOOD00561)
Hard wheat (FooDB: FOOD00242)
White bread (FooDB: FOOD00987)

Cereal product

Bread products

Other bread product (FooDB: FOOD00805)

Flat bread

Crisp bread (FooDB: FOOD00640)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Miso (FooDB: FOOD00695)
Soy milk (FooDB: FOOD00736)
Soy sauce (FooDB: FOOD00694)
Tofu (FooDB: FOOD00696)

Baking good

Sugar

Sugar (FooDB: FOOD00651)

Dressing

Salad dressing (FooDB: FOOD00645)

Condiment

Substitute

Sugar substitute (FooDB: FOOD00656)

Seasoning

Salt (FooDB: FOOD00647)
Vinegar (FooDB: FOOD00628)

Sauce

Sauce (FooDB: FOOD00646)

Unclassified food or beverage

Unclassified food or beverage (FooDB: FOOD00672)

Dish

Ground meat

Sausage (FooDB: FOOD00652)
Meatball (FooDB: FOOD00653)
Pate (FooDB: FOOD00655)
Cold cut (FooDB: FOOD00770)

Other dish

Dumpling (FooDB: FOOD00669)
Other dish (FooDB: FOOD00836)
Pizza (FooDB: FOOD00637)
Soup (FooDB: FOOD00670)

Sandwich

Hamburger (FooDB: FOOD00705)
Other sandwich (FooDB: FOOD00755)

Fat and oil

Vegetable fat

Margarine-like spread (FooDB: FOOD00844)
Margarine (FooDB: FOOD00843)

Animal fat

Fish oil (FooDB: FOOD00990)

Milk and milk product

Other milk product

Butter (FooDB: FOOD00648)
Casein (FooDB: FOOD00659)
Whey (FooDB: FOOD00658)
Cream (FooDB: FOOD00650)
Dried milk (FooDB: FOOD00689)

Fermented milk product

Cheese (FooDB: FOOD00617)
Yogurt (FooDB: FOOD00620)
Ymer (FooDB: FOOD00638)

Unfermented milk

Fermented milk

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Confectionery

Candy

Dessert

Pastry (FooDB: FOOD00641)
Gelatin dessert (FooDB: FOOD00725)

Other confectionery

Honey (FooDB: FOOD00626)
Marzipan (FooDB: FOOD00644)
Toffee (FooDB: FOOD00635)
Meringue (FooDB: FOOD00680)

Frozen dessert

Ice cream (FooDB: FOOD00624)
Other frozen dessert (FooDB: FOOD00729)

Spread

Chocolate spread (FooDB: FOOD00676)

Cocoa and cocoa product

Cocoa product

Coffee and coffee product

Coffee

Snack

Cracker (FooDB: FOOD00787)
Other snack food (FooDB: FOOD00639)

Egg

Eggs (FooDB: FOOD00619)

Tea

Process

Naturally occurring process

Biological process

Biochemical pathway

Magnesium salicylate Action Pathway (HMDB: HMDB0001043)

Drug action pathway

Acetaminophen Action Pathway (PathBank: SMP0000710)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-Sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium Salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-Choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)

Metabolic pathway

Alpha Linolenic Acid and Linoleic Acid Metabolism (PathBank: SMP0000018)
Arachidonic Acid Metabolism (PathBank: SMP0000075)

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0000353)

Protein pathway

Fc Epsilon Receptor I Signaling in Mast Cells (PathBank: SMP0000358)
GnRH Signaling Pathway (PathBank: SMP0063811)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0001043)

Cellular process

Cell signaling (HMDB: HMDB0001043)

Chemical reaction

Lipid peroxidation (HMDB: HMDB0001043)

anti dermatitic (HMDB: HMDB0001043)
anti eczemic (HMDB: HMDB0001043)
anti leukotriene-B4 (HMDB: HMDB0001043)
anti psoriatic (HMDB: HMDB0001043)
cancer preventive (HMDB: HMDB0001043)
coagulant (HMDB: HMDB0001043)
hepatoprotective (HMDB: HMDB0001043)
immunological adjuvant (HMDB: HMDB0001043)
insulinogenic (HMDB: HMDB0001043)
myocontractant (HMDB: HMDB0001043)
pyrogenic (HMDB: HMDB0001043)
Membrane stabilizer (HMDB: HMDB0001043)

Nutrient

Nutrient (HMDB: HMDB0001043)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

immunological adjuvant (HMDB: HMDB0001043)

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001043)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001043)

Biomarker

Diabetes mellitus type 2 (MarkerDB: MDB00029993)
Schizophrenia (MarkerDB: MDB00029993)
Isovaleric acidemia (MarkerDB: MDB00029993)
Hypertension (MarkerDB: MDB00029993)

Emulsifier (HMDB: HMDB0001043)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	6.98	SANGSTER (1993)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	180.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000233

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	6.8	ALOGPS
logP	6.59	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	99.95 m³·mol⁻¹	ChemAxon
Polarizability	37.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	186.319	31661259
DarkChem	[M+H]+	186.319	31661259
DarkChem	[M-H]-	186.871	31661259
DarkChem	[M-H]-	186.871	31661259
AllCCS	[M+H]+	182.834	32859911
AllCCS	[M-H]-	183.125	32859911
DeepCCS	[M+H]+	184.659	30932474
DeepCCS	[M-H]-	182.301	30932474
DeepCCS	[M-2H]-	215.187	30932474
DeepCCS	[M+Na]+	190.753	30932474
AllCCS	[M+H]+	182.8	32859911
AllCCS	[M+H-H2O]+	179.9	32859911
AllCCS	[M+NH4]+	185.6	32859911
AllCCS	[M+Na]+	186.4	32859911
AllCCS	[M-H]-	183.1	32859911
AllCCS	[M+Na-2H]-	184.9	32859911
AllCCS	[M+HCOO]-	186.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arachidonic acid	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	3706.3	Standard polar	33892256
Arachidonic acid	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	2124.7	Standard non polar	33892256
Arachidonic acid	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	2320.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Arachidonic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2368.7	Semi standard non polar	33892256
Arachidonic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2615.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Arachidonic acid GC-MS (1 TMS)	splash10-005c-9800000000-87c290971fc8a628fb23	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Arachidonic acid GC-MS (Non-derivatized)	splash10-005c-9800000000-87c290971fc8a628fb23	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Arachidonic acid GC-EI-TOF (Non-derivatized)	splash10-0006-6900000000-6870df266b6c73f2a4a1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arachidonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7390000000-7004b9cd28a9b3d9c991	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arachidonic acid GC-MS (1 TMS) - 70eV, Positive	splash10-05i9-9252000000-475d13959ee8ce889646	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arachidonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arachidonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0nmi-0913000000-95846e8d5e8afd29664b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 10V, Negative-QTOF	splash10-005l-0902100000-6fc8730bd28daa779b66	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 20V, Negative-QTOF	splash10-005l-0902100000-6fc8730bd28daa779b66	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid ESI-TOF , Negative-QTOF	splash10-005l-0902100000-6fc8730bd28daa779b66	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 10V, Negative-QTOF	splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 30V, Negative-QTOF	splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 10V, Negative-QTOF	splash10-0udi-0009000000-6bd9d0477c122d3eed94	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 20V, Negative-QTOF	splash10-0udi-0009000000-510ea33e558fa238a1d2	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid ESI-TOF , Negative-QTOF	splash10-0udi-0009000000-73a6b21464acba15463c	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 10V, Negative-QTOF	splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 30V, Negative-QTOF	splash10-0udi-0049000000-102d050109d3c78b1a25	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid LC-ESI-IT , negative-QTOF	splash10-0a4i-0090000000-2fb9003e782ec3d05e20	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid LC-ESI-QTOF , negative-QTOF	splash10-0nmi-0913000000-95846e8d5e8afd29664b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid LC-ESI-TOF , negative-QTOF	splash10-0udi-0009000000-6bd9d0477c122d3eed94	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid LC-ESI-TOF , negative-QTOF	splash10-0udi-0009000000-510ea33e558fa238a1d2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid LC-ESI-TOF , negative-QTOF	splash10-0udi-0049000000-102d050109d3c78b1a25	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid 10V, Positive-QTOF	splash10-0udi-0009000000-6bd9d0477c122d3eed94	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid 20V, Positive-QTOF	splash10-0udi-0009000000-510ea33e558fa238a1d2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Arachidonic acid 6V, Positive-QTOF	splash10-0a4i-1934000000-3fb5938d1b4795217a97	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonic acid 10V, Positive-QTOF	splash10-0a4r-1196000000-a42ea66033eb9771d36d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonic acid 20V, Positive-QTOF	splash10-0a4j-5691000000-2bc7b1ae5487233dfce8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonic acid 40V, Positive-QTOF	splash10-0007-7950000000-b15a8d382a4b3ad62d08	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonic acid 10V, Negative-QTOF	splash10-0udi-0029000000-28a9bbfed5fabd10c0c2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonic acid 20V, Negative-QTOF	splash10-0zfr-2079000000-3f6e64ef7522a793e9a9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonic acid 40V, Negative-QTOF	splash10-0a4i-9130000000-9c0c8bb5fc8e30bf53c7	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Adipose Tissue
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Lung
Neuron
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen
Testis
Thyroid Gland

Pathways

Name	SMPDB/PathBank	KEGG
alpha-Linolenic acid metabolism	Not Available
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.94 +/- 0.058 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	14 +/- 12 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	31.6 +/- 21.7 uM	Adult (>18 years old)	Both	Normal	18633173	details
Blood	Detected and Quantified	55.4 +/- 4.48 uM	Adult (>18 years old)	Both	Normal	25004141	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected and Quantified	31.5 +/- 25.8 uM	Adult (>18 years old)	Male	Normal	18633173	details
Blood	Detected and Quantified	31.7 +/- 30.4 uM	Adult (>18 years old)	Female	Normal	18633173	details
Blood	Detected and Quantified	5.263 +/- 2.072 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	594.5 +/- 144.9 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20143319	details
Blood	Detected and Quantified	348.150 +/- 52.551 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	344.865 +/- 55.835 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	312.0208 +/- 62.404 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	348.150 +/- 49.266 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	12 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	15 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	16 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	17 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	19 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	20 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	66 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	82 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	86 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	132 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	134 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	158 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	475.750 +/- 136.599 uM	Adult (>18 years old)	Both	Normal	17313719	details
Blood	Detected and Quantified	349.398 +/- 84.476 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	8.50 +/- 1.58 uM	Adult (>18 years old)	Female	Normal	14634727	details
Blood	Detected and Quantified	660 +/- 130 uM	Adult (>18 years old)	Female	Normal	14608088	details
Blood	Detected and Quantified	590 +/- 120 uM	Adult (>18 years old)	Male	Normal	14608088	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.35 (0.03 - 0.66) uM	Adult (>18 years old)	Not Specified	Normal	2835791	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	2.45 +/- 1.63 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	14643447	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	34.3 +/- 27.8 uM	Adult (>18 years old)	Both	Hypertension	18633173	details
Blood	Detected and Quantified	38.5 +/- 2.18 uM	Adult (>18 years old)	Both	Schizophrenia	25004141	details
Blood	Detected and Quantified	34.0 +/- 28.6 uM	Adult (>18 years old)	Male	Essential hypertension	18633173	details
Blood	Detected and Quantified	34.9 +/- 26.4 uM	Adult (>18 years old)	Female	Essential hypertension	18633173	details
Blood	Detected and Quantified	415.6 +/- 114.3 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Pancreatic ductal adenocarcinoma	20143319	details
Blood	Detected and Quantified	10.27 +/- 2.11 uM	Adult (>18 years old)	Female	Gestational diabetes mellitus (GDM)	14634727	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Interstitial cystitis	27188581	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Gestational diabetes
Min Y, Ghebremeskel K, Lowy C, Thomas B, Crawford MA: Adverse effect of obesity on red cell membrane arachidonic and docosahexaenoic acids in gestational diabetes. Diabetologia. 2004 Jan;47(1):75-81. Epub 2003 Nov 22. [PubMed:14634727 ]
Hypertension
Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Essential hypertension
Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Schizophrenia
Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Bladder infections
Braundmeier-Fleming A, Russell NT, Yang W, Nas MY, Yaggie RE, Berry M, Bachrach L, Flury SC, Marko DS, Bushell CB, Welge ME, White BA, Schaeffer AJ, Klumpp DJ: Stool-based biomarkers of interstitial cystitis/bladder pain syndrome. Sci Rep. 2016 May 18;6:26083. doi: 10.1038/srep26083. [PubMed:27188581 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

145500 (Hypertension)
181500 (Schizophrenia)
243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB04557

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15843

Food Biomarker Ontology

Not Available

VMH ID

ARACHD

MarkerDB ID

MDB00029993

Good Scents ID

Not Available

References

Synthesis Reference

Dai, Chuanchao; Yuan, Zhilin; Wang, Anqi. Production of arachidonic acid and eicosapentaenoic acid with organic wastewater of soybean products. Zhongguo Youzhi (2004), 29(5), 31-33.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 115 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Enzyme Details

2. Calcium-dependent phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:: PLA2G5
Uniprot ID:: P39877
Molecular weight:: 15674.065

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid	details

Enzyme Details

3. Group IIF secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:: PLA2G2F
Uniprot ID:: Q9BZM2
Molecular weight:: 23256.29

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid	details

Enzyme Details

4. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid	details

Enzyme Details

5. Phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G1B
Uniprot ID:: P04054
Molecular weight:: 16359.535

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid	details

Enzyme Details

6. Group XIIB secretory phospholipase A2-like protein

General function:: Involved in phospholipase A2 activity
Specific function:: Not known; does not seem to have catalytic activity.
Gene Name:: PLA2G12B
Uniprot ID:: Q9BX93
Molecular weight:: Not Available

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid	details

Enzyme Details

7. Group 10 secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:: PLA2G10
Uniprot ID:: O15496
Molecular weight:: 18153.04

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid	details

Enzyme Details

8. Galactoside-binding soluble lectin 13

General function:: Involved in sugar binding
Specific function:: Has lysophospholipase activity.
Gene Name:: LGALS13
Uniprot ID:: Q9UHV8
Molecular weight:: 16118.44

Enzyme Details

9. Group IIE secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:: PLA2G2E
Uniprot ID:: Q9NZK7
Molecular weight:: 15988.525

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid	details

Enzyme Details

10. Group XIIA secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:: PLA2G12A
Uniprot ID:: Q9BZM1
Molecular weight:: 21066.99

Reactions

Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid	details

Transporters

Enzyme Details

1. Long-chain fatty acid transport protein 1

General function:: Lipid transport and metabolism
Specific function:: Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:: SLC27A1
Uniprot ID:: Q6PCB7
Molecular weight:: 71107.5

Enzyme Details

2. Solute carrier organic anion transporter family member 2A1

General function:: Not Available
Specific function:: May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, as well as PGE1, PGE2 and PGF2A
Gene Name:: SLCO2A1
Uniprot ID:: Q92959
Molecular weight:: 70117.0

References

Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. [PubMed:7754369 ]

Only showing the first 10 proteins. There are 115 proteins in total.

Show all enzymes and transporters

Showing metabocard for Arachidonic acid (HMDB0001043)

MOL for HMDB0001043 (Arachidonic acid)

3D MOL for HMDB0001043 (Arachidonic acid)

3D SDF for HMDB0001043 (Arachidonic acid)

3D-SDF for HMDB0001043 (Arachidonic acid)

PDB for HMDB0001043 (Arachidonic acid)

3D PDB for HMDB0001043 (Arachidonic acid)

SMILES for HMDB0001043 (Arachidonic acid)

INCHI for HMDB0001043 (Arachidonic acid)

Structure for HMDB0001043 (Arachidonic acid)

3D Structure for HMDB0001043 (Arachidonic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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Reactions

Transporters

References