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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001193

Secondary Accession Numbers

HMDB01193

Metabolite Identification

Common Name

5(S)-Hydroperoxyeicosatetraenoic acid

Description

5(S)-Hydroperoxyeicosatetraenoic acid is a lipid hydroperoxide precursor of leukotrienes. The first step of biosynthesis of leukotrienes is conversion of arachidonic acid into 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid [5(S)-HpETE] by 5- lipoxygenases (5-LOX). Lipid hydroperoxides undergo homolytic decomposition into bifunctional electrophiles, which react with DNA bases to form DNA adducts. These DNA modifications are proposed to be involved in the etiology of cancer, cardiovascular disease, and neurodegeneration. 5-LOX, the enzyme responsible for the formation of 5(S)-HpETE in vivo, is expressed primarily in leukocytes, including monocytes and macrophages. Studies have implicated the 5-LOX pathway as an important mediator in the pathology of atherosclerosis. (PMID: 15777099 ). Endogenously generated 5-hydroperoxyeicosatetraenoic acid is the preferred substrate for human leukocyte leukotriene A4 synthase activity. Thus, the arachidonic acid moiety is preferentially converted to LTA4 in a concerted reaction without dissociation of a 5-HPETE intermediate. (PMID: 3036580 ).

Structure

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

HMDB0001193
     RDKit          3D
5(S)-Hydroperoxyeicosatetraenoic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
   -8.5095    0.5801    1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4083   -0.3590    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1929   -0.0210    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9888   -0.8512    1.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5168   -0.7172   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1652    0.6836   -0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9827    1.1152   -1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333    0.2162   -1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760    0.2065   -2.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916    0.5720   -2.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9778    1.0800   -2.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    1.3116   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5404    0.7322    0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5697   -0.2648    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338   -0.8133    1.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2888   -1.8332    0.8405 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6422   -1.1400    0.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7020   -0.0457   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9790    0.7283   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2499    1.4109    1.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5283    1.3992    2.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4373    2.1454    1.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2163   -2.3607   -0.4280 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -3.6802   -0.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2771    1.6030    0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4924    0.3032    0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5679    0.5018    2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2620   -0.1541   -0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7838   -1.3856    0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5189   -0.1324    2.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0131    1.0682    1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904   -0.5404    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2323   -1.9215    1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334   -1.4985   -0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4611   -0.9234   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9470    1.4810   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8445    2.1944   -1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1485    0.2325   -0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2480   -0.8697   -1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9779   -0.1599   -3.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226    0.4704   -4.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    2.0283   -2.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8577    0.3728   -2.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1207    2.0800   -0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3034    1.0390    1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089   -0.5727   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549   -0.4701    2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001   -2.6463    1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6495   -0.7390    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4671   -1.8673    0.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.5098   -1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8550    0.6461    0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404    1.4549   -0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433    0.0221   -0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7053    2.8045    0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6181   -4.0064    0.3319 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  2  0
 15 16  1  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
 16 23  1  0
 23 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  1
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 24 56  1  0
M  END

  Mrv0541 02231218592D          

 24 23  0  0  1  0            999 V2000
   -0.2098    1.0678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0373    1.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4996    0.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288    2.3760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544    0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2128    1.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5836    2.8413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4751    1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9260    0.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2952    1.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    1.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0045   -0.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3562    0.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    1.8916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486   -1.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5209   -1.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8116   -1.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946   -1.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784   -1.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272   -1.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326   -1.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8383   -1.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5476   -1.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2532   -1.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  8 10  2  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
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001193

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1

> <INCHI_KEY>
JNUUNUQHXIOFDA-JGKLHWIESA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.53405647352225

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid

> <ALOGPS_LOGP>
5.92

> <JCHEM_LOGP>
5.805695121333333

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712375181179874

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.3904738868948

> <JCHEM_PKA_STRONGEST_BASIC>
-4.236807969194996

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
102.81970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-HpETE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001193
     RDKit          3D
5(S)-Hydroperoxyeicosatetraenoic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
   -8.5095    0.5801    1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4083   -0.3590    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1929   -0.0210    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9888   -0.8512    1.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5168   -0.7172   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1652    0.6836   -0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9827    1.1152   -1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333    0.2162   -1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760    0.2065   -2.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916    0.5720   -2.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9778    1.0800   -2.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    1.3116   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5404    0.7322    0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5697   -0.2648    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338   -0.8133    1.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2888   -1.8332    0.8405 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6422   -1.1400    0.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7020   -0.0457   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9790    0.7283   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2499    1.4109    1.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5283    1.3992    2.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4373    2.1454    1.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2163   -2.3607   -0.4280 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -3.6802   -0.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2771    1.6030    0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4924    0.3032    0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5679    0.5018    2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2620   -0.1541   -0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7838   -1.3856    0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5189   -0.1324    2.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0131    1.0682    1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904   -0.5404    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2323   -1.9215    1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334   -1.4985   -0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4611   -0.9234   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9470    1.4810   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8445    2.1944   -1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1485    0.2325   -0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2480   -0.8697   -1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9779   -0.1599   -3.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226    0.4704   -4.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    2.0283   -2.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8577    0.3728   -2.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1207    2.0800   -0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3034    1.0390    1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089   -0.5727   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549   -0.4701    2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001   -2.6463    1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6495   -0.7390    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4671   -1.8673    0.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.5098   -1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8550    0.6461    0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404    1.4549   -0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433    0.0221   -0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7053    2.8045    0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6181   -4.0064    0.3319 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  2  0
 15 16  1  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
 16 23  1  0
 23 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  1
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.392   1.993   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.936   1.986   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.933   1.218   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.427   4.435   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.275   1.196   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.264   1.993   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.089   5.304   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.620   1.972   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.595   1.218   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.151   1.965   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.926   1.993   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.475  -0.634   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.265   1.224   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.926   3.531   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -6.251  -3.282   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.706  -3.275   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.382  -2.492   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.043  -3.254   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.520  -3.246   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.797  -2.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.114  -3.232   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.431  -2.463   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.756  -3.225   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.073  -2.449   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    9                                                       
CONECT    7    4                                                            
CONECT    8    5   10                                                       
CONECT    9    6   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13   14                                                  
CONECT   12   10   15                                                       
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0001193
HETATM    1  C1  UNL     1      -8.509   0.580   1.022  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.408  -0.359   0.550  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.193  -0.021   1.384  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.989  -0.851   1.074  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.517  -0.717  -0.373  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.165   0.684  -0.688  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.983   1.115  -1.067  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.833   0.216  -1.225  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.276   0.207  -2.578  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.092   0.572  -2.904  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.978   1.080  -2.075  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.850   1.312  -0.668  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.540   0.732   0.297  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.570  -0.265   0.048  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.234  -0.813   1.071  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.289  -1.833   0.840  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.642  -1.140   0.989  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.702  -0.046  -0.043  1.00  0.00           C  
HETATM   19  C19 UNL     1       6.979   0.728  -0.023  1.00  0.00           C  
HETATM   20  C20 UNL     1       7.250   1.411   1.253  1.00  0.00           C  
HETATM   21  O1  UNL     1       6.528   1.399   2.266  1.00  0.00           O  
HETATM   22  O2  UNL     1       8.437   2.145   1.333  1.00  0.00           O  
HETATM   23  O3  UNL     1       4.216  -2.361  -0.428  1.00  0.00           O  
HETATM   24  O4  UNL     1       4.063  -3.680  -0.413  1.00  0.00           O  
HETATM   25  H1  UNL     1      -8.277   1.603   0.719  1.00  0.00           H  
HETATM   26  H2  UNL     1      -9.492   0.303   0.581  1.00  0.00           H  
HETATM   27  H3  UNL     1      -8.568   0.502   2.126  1.00  0.00           H  
HETATM   28  H4  UNL     1      -7.262  -0.154  -0.536  1.00  0.00           H  
HETATM   29  H5  UNL     1      -7.784  -1.386   0.733  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.519  -0.132   2.443  1.00  0.00           H  
HETATM   31  H7  UNL     1      -6.013   1.068   1.255  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.190  -0.540   1.779  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.232  -1.921   1.209  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.833  -1.498  -0.659  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.461  -0.923  -0.978  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.947   1.481  -0.611  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.845   2.194  -1.276  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.149   0.232  -0.378  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.248  -0.870  -1.133  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.978  -0.160  -3.385  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.123   0.470  -4.025  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.438   2.028  -2.591  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.858   0.373  -2.252  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.121   2.080  -0.340  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.303   1.039   1.336  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.809  -0.573  -0.931  1.00  0.00           H  
HETATM   47  H23 UNL     1       2.955  -0.470   2.052  1.00  0.00           H  
HETATM   48  H24 UNL     1       4.200  -2.646   1.605  1.00  0.00           H  
HETATM   49  H25 UNL     1       5.649  -0.739   2.021  1.00  0.00           H  
HETATM   50  H26 UNL     1       6.467  -1.867   0.860  1.00  0.00           H  
HETATM   51  H27 UNL     1       5.601  -0.510  -1.040  1.00  0.00           H  
HETATM   52  H28 UNL     1       4.855   0.646   0.176  1.00  0.00           H  
HETATM   53  H29 UNL     1       6.940   1.455  -0.864  1.00  0.00           H  
HETATM   54  H30 UNL     1       7.843   0.022  -0.192  1.00  0.00           H  
HETATM   55  H31 UNL     1       8.705   2.805   0.601  1.00  0.00           H  
HETATM   56  H32 UNL     1       4.618  -4.006   0.332  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7   36
CONECT    7    8   37
CONECT    8    9   38   39
CONECT    9   10   10   40
CONECT   10   11   41
CONECT   11   12   42   43
CONECT   12   13   13   44
CONECT   13   14   45
CONECT   14   15   15   46
CONECT   15   16   47
CONECT   16   17   23   48
CONECT   17   18   49   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   21   22
CONECT   22   55
CONECT   23   24
CONECT   24   56
END

HMDB0001193
     RDKit          3D
5(S)-Hydroperoxyeicosatetraenoic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
   -8.5095    0.5801    1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4083   -0.3590    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1929   -0.0210    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9888   -0.8512    1.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5168   -0.7172   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1652    0.6836   -0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9827    1.1152   -1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333    0.2162   -1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760    0.2065   -2.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916    0.5720   -2.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9778    1.0800   -2.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    1.3116   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5404    0.7322    0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5697   -0.2648    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338   -0.8133    1.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2888   -1.8332    0.8405 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6422   -1.1400    0.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7020   -0.0457   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9790    0.7283   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2499    1.4109    1.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5283    1.3992    2.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4373    2.1454    1.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2163   -2.3607   -0.4280 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -3.6802   -0.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2771    1.6030    0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4924    0.3032    0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5679    0.5018    2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2620   -0.1541   -0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7838   -1.3856    0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5189   -0.1324    2.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0131    1.0682    1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1904   -0.5404    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2323   -1.9215    1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334   -1.4985   -0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4611   -0.9234   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9470    1.4810   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8445    2.1944   -1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1485    0.2325   -0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2480   -0.8697   -1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9779   -0.1599   -3.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226    0.4704   -4.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    2.0283   -2.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8577    0.3728   -2.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1207    2.0800   -0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3034    1.0390    1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089   -0.5727   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549   -0.4701    2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001   -2.6463    1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6495   -0.7390    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4671   -1.8673    0.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007   -0.5098   -1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8550    0.6461    0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404    1.4549   -0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433    0.0221   -0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7053    2.8045    0.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6181   -4.0064    0.3319 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  2  0
 15 16  1  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
 16 23  1  0
 23 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  1
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid	ChEBI
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoate	ChEBI
(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoate	ChEBI
(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid	ChEBI
(S)-5-HPETE	ChEBI
5(S)-Hydroperoxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acid	ChEBI
5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid	ChEBI
5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-eicosatetraenoic acid	ChEBI
5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-icosatetraenoic acid	ChEBI
5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate	ChEBI
5S-HpETE	ChEBI
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoate	Generator
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acid	Generator
5(S)-Hydroperoxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoate	Generator
5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate	Generator
5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-eicosatetraenoate	Generator
5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-icosatetraenoate	Generator
5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid	Generator
5(S)-Hydroperoxyeicosatetraenoate	Generator
5-HPETE	HMDB
5-Hydroperoxy-6,8,11,14-eicosatetraenoic acid	HMDB
6,8,11,14-Eicosatetraenoic acid 5-hydroperoxide	HMDB
Arachidonic acid 5-hydroperoxide	HMDB
cis,trans-5-Hydroperoxy-6,8,11,14-eicosatetraenoic acid	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid

Traditional Name

5-HpETE

CAS Registry Number

71774-08-8

SMILES

CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1

InChI Key

JNUUNUQHXIOFDA-JGKLHWIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroperoxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroperoxyeicosatetraenoic acid
Long-chain fatty acid
Hydroperoxy fatty acid
Fatty acid
Unsaturated fatty acid
Allylic hydroperoxide
Hydroperoxide
Carboxylic acid derivative
Alkyl hydroperoxide
Carboxylic acid
Peroxol
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

HPETE (CHEBI:15632 )
Hydroperoxy fatty acids (C05356 )
Leukotrienes (C05356 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C05356 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060012 )

Ontology

Not Available

Exogenous (FooDB: )

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Oilseed crop

Other seed

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
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)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)

Mushroom

Tuber

Onion-family vegetable

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Heart of palm (FooDB: FOOD00718)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Juniperus communis (FooDB: FOOD00895)
Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Albizia gummifera (FooDB: FOOD00896)

Cereal and cereal product

Leavened bread

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)
Bulgur (FooDB: FOOD00741)

Flat bread

Sweet bread

Raisin bread (FooDB: FOOD00817)

Other bread

Potato bread (FooDB: FOOD00811)

Dough

Sourdough (FooDB: FOOD00275)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Green lentil (FooDB: FOOD00970)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Miso (FooDB: FOOD00695)
Soy milk (FooDB: FOOD00736)
Soy sauce (FooDB: FOOD00694)
Tofu (FooDB: FOOD00696)
Soy cream (FooDB: FOOD00784)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012870)

Role

Not Available

Physical Properties

State

Solid

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	5.92	ALOGPS
logP	5.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	102.82 m³·mol⁻¹	ChemAxon
Polarizability	39.53 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]+	194.634	31661259
DarkChem	[M-H]-	190.767	31661259
AllCCS	[M+H]+	190.551	32859911
AllCCS	[M-H]-	188.14	32859911
DeepCCS	[M+H]+	190.024	30932474
DeepCCS	[M-H]-	187.666	30932474
DeepCCS	[M-2H]-	221.076	30932474
DeepCCS	[M+Na]+	196.353	30932474
AllCCS	[M+H]+	190.6	32859911
AllCCS	[M+H-H2O]+	187.7	32859911
AllCCS	[M+NH4]+	193.2	32859911
AllCCS	[M+Na]+	193.9	32859911
AllCCS	[M-H]-	188.1	32859911
AllCCS	[M+Na-2H]-	190.0	32859911
AllCCS	[M+HCOO]-	192.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5(S)-Hydroperoxyeicosatetraenoic acid	CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO	4173.3	Standard polar	33892256
5(S)-Hydroperoxyeicosatetraenoic acid	CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO	2413.6	Standard non polar	33892256
5(S)-Hydroperoxyeicosatetraenoic acid	CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO	2675.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5(S)-Hydroperoxyeicosatetraenoic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)OO	2761.3	Semi standard non polar	33892256
5(S)-Hydroperoxyeicosatetraenoic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)OO	3004.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ufv-7293000000-1f097659cf0dcff9bef9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00bl-9145000000-04747e5703a025ef8f4f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 10V, Positive-QTOF	splash10-014i-0119000000-5146d59d15dbfb1648ac	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 20V, Positive-QTOF	splash10-000l-5895000000-636edd63bf1c315085fb	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 40V, Positive-QTOF	splash10-0f96-7970000000-59e419db47612aac9e21	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 10V, Negative-QTOF	splash10-000i-0029000000-27b34dc78df443e7b2e7	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 20V, Negative-QTOF	splash10-0fri-4189000000-4d5ecf358e00eaff1450	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 40V, Negative-QTOF	splash10-0a4l-9160000000-7865a2863663a5eb39ab	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 10V, Negative-QTOF	splash10-000i-0009000000-4313d8567d98daeec5be	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 20V, Negative-QTOF	splash10-0k9i-2069000000-56e8fbe6c944c9901664	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 40V, Negative-QTOF	splash10-052f-9330000000-a6266812ce67a6e4e4f6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 10V, Positive-QTOF	splash10-000i-1369000000-fdc7ed645955c857b4f6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 20V, Positive-QTOF	splash10-00li-6924000000-769a1698f7fc3038abd9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5(S)-Hydroperoxyeicosatetraenoic acid 40V, Positive-QTOF	splash10-05nf-9300000000-13e0c97d67ef1cdf5fc0	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022480

KNApSAcK ID

Not Available

Chemspider ID

4444340

KEGG Compound ID

C05356

BioCyc ID

Not Available

BiGG ID

45650

Wikipedia Link

Not Available

METLIN ID

6070

PubChem Compound

5280778

PDB ID

Not Available

ChEBI ID

15632

Food Biomarker Ontology

Not Available

VMH ID

5HPET

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Dussault, Patrick; Lee, In Quen. A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE. Journal of Organic Chemistry (1995), 60(1), 218-26.

Material Safety Data Sheet (MSDS)

Not Available

General References

Jian W, Lee SH, Arora JS, Silva Elipe MV, Blair IA: Unexpected formation of etheno-2'-deoxyguanosine adducts from 5(S)-hydroperoxyeicosatetraenoic acid: evidence for a bis-hydroperoxide intermediate. Chem Res Toxicol. 2005 Mar;18(3):599-610. [PubMed:15777099 ]
Puustinen T, Scheffer MM, Samuelsson B: Endogenously generated 5-hydroperoxyeicosatetraenoic acid is the preferred substrate for human leukocyte leukotriene A4 synthase activity. FEBS Lett. 1987 Jun 15;217(2):265-8. [PubMed:3036580 ]

Enzymes

Enzyme Details

1. Glutathione peroxidase 7

General function:: Involved in glutathione peroxidase activity
Specific function:: It protects esophageal epithelia from hydrogen peroxide-induced oxidative stress. It suppresses acidic bile acid-induced reactive oxigen species (ROS) and protects against oxidative DNA damage and double-strand breaks.
Gene Name:: GPX7
Uniprot ID:: Q96SL4
Molecular weight:: 20995.88

Reactions

Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Water	details

Enzyme Details

2. Epididymal secretory glutathione peroxidase

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione. May constitute a glutathione peroxidase-like protective system against peroxide damage in sperm membrane lipids.
Gene Name:: GPX5
Uniprot ID:: O75715
Molecular weight:: 25202.14

Reactions

Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Water	details

Enzyme Details

3. Glutathione peroxidase 6

General function:: Involved in glutathione peroxidase activity
Specific function:: Not Available
Gene Name:: GPX6
Uniprot ID:: P59796
Molecular weight:: 24970.46

Reactions

Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Water	details

Enzyme Details

4. Glutathione peroxidase 1

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects the hemoglobin in erythrocytes from oxidative breakdown.
Gene Name:: GPX1
Uniprot ID:: P07203
Molecular weight:: 22087.94

Reactions

Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Water	details

Enzyme Details

5. Phospholipid hydroperoxide glutathione peroxidase, mitochondrial

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects cells against membrane lipid peroxidation and cell death. Required for normal sperm development and male fertility. Could play a major role in protecting mammals from the toxicity of ingested lipid hydroperoxides. Essential for embryonic development. Protects from radiation and oxidative damage (By similarity).
Gene Name:: GPX4
Uniprot ID:: P36969
Molecular weight:: 25046.57

Enzyme Details

6. Glutathione peroxidase 3

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione.
Gene Name:: GPX3
Uniprot ID:: P22352
Molecular weight:: 25552.185

Reactions

Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Water	details

Enzyme Details

7. Glutathione peroxidase 2

General function:: Involved in glutathione peroxidase activity
Specific function:: Could play a major role in protecting mammals from the toxicity of ingested organic hydroperoxides. Tert-butyl hydroperoxide, cumene hydroperoxide and linoleic acid hydroperoxide but not phosphatidycholine hydroperoxide, can act as acceptors.
Gene Name:: GPX2
Uniprot ID:: P18283
Molecular weight:: 21953.835

Reactions

Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Water	details

Enzyme Details

8. Arachidonate 5-lipoxygenase

General function:: Involved in metal ion binding
Specific function:: Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:: ALOX5
Uniprot ID:: P09917
Molecular weight:: 77982.595

Reactions

Arachidonic acid + Oxygen → 5(S)-Hydroperoxyeicosatetraenoic acid	details
5(S)-Hydroperoxyeicosatetraenoic acid → Leukotriene A4 + Water	details

Showing metabocard for 5(S)-Hydroperoxyeicosatetraenoic acid (HMDB0001193)

MOL for HMDB0001193 (5(S)-Hydroperoxyeicosatetraenoic acid)

3D MOL for HMDB0001193 (5(S)-Hydroperoxyeicosatetraenoic acid)

3D SDF for HMDB0001193 (5(S)-Hydroperoxyeicosatetraenoic acid)

3D-SDF for HMDB0001193 (5(S)-Hydroperoxyeicosatetraenoic acid)

PDB for HMDB0001193 (5(S)-Hydroperoxyeicosatetraenoic acid)

3D PDB for HMDB0001193 (5(S)-Hydroperoxyeicosatetraenoic acid)

SMILES for HMDB0001193 (5(S)-Hydroperoxyeicosatetraenoic acid)

INCHI for HMDB0001193 (5(S)-Hydroperoxyeicosatetraenoic acid)

Structure for HMDB0001193 (5(S)-Hydroperoxyeicosatetraenoic acid)

3D Structure for HMDB0001193 (5(S)-Hydroperoxyeicosatetraenoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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