Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 19:56:15 UTC

Update Date

2022-03-07 02:49:29 UTC

HMDB ID

HMDB0005998

Secondary Accession Numbers

HMDB05998

Metabolite Identification

Common Name

20-Hydroxyeicosatetraenoic acid

Description

20-Hydroxyeicosatetraenoic acid (20-HETE) is a metabolite of arachidonic acid. Cytochrome P450 enzymes of the 4A and 4F families catalyze the omega-hydroxylation of arachidonic acid and produce 20-HETE. 20-HETE is a potent constrictor of renal, cerebral, and mesenteric arteries. The vasoconstrictor response to 20-HETE is associated with activation of protein kinase, Rho kinase, and the mitogen-activated protein (MAP) kinase pathway C. 20-HETE also increases intracellular Ca2+ by causing the depolarization of vascular smooth muscle membrane secondary to blocking the large-conductance Ca2+-activated K+-channels and by a direct effect on L-type Ca channels. Elevations in the production of 20-HETE mediate the myogenic response of skeletal, renal, and cerebral arteries to elevations in transmural pressure. There is an important interaction between nitric oxide (NO) and the formation of 20-HETE production. NO inhibits the formation of 20-HETE formation in renal and cerebral arteries. A fall in levels of 20-HETE contributes to the cyclic GMP-independent dilator effect of NO to activate the large-conductance Ca2+-activated K+-channels and to dilate the cerebral arteries (PMID: 16258232 ).

Structure

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

HMDB0005998
     RDKit          3D
20-Hydroxyeicosatetraenoic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
    7.8835    0.3581    0.1874 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3130    1.0473   -0.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8328    2.2904   -0.9930 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1411    0.5545   -1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.7504   -0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    0.0273    0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -1.4254    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1267   -2.2865    0.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612   -1.9175    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -2.4863    0.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515   -1.7621    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959   -0.2901    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    0.2455   -1.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0932    0.9822   -1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3191    1.3965   -0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4601    0.8630   -1.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3419    0.0411   -1.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3437   -0.4810    0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167   -0.0674    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8141   -0.6048    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1004   -0.2116    0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2269    1.2983    0.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2540    1.8809   -0.3039 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3452    2.8702   -0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0416    1.1318   -2.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2331   -0.5156   -1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7427    1.8362   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0461    0.3791   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7654    0.4019    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0130    0.3626    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9489   -1.8013   -0.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2865   -3.3828    0.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9017   -2.5073    2.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7427   -0.9053    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716   -3.6070    0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0435   -2.2117   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693    0.1611    0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    0.0043    0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -0.0139   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    1.3321   -2.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888    2.5436   -0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3137    1.1431    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692    1.1864   -2.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758   -0.3368   -1.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4491   -0.2605    0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3757   -1.6188    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -0.4720    1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6336    1.0466    0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7503   -1.7095    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8757   -0.1467   -0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9507   -0.5831    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1641   -0.6017    1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2045    1.5129    1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4581    1.7632    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8538    2.7962   -0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
M  END


  Mrv1652303291817492D          

 23 22  0  0  0  0            999 V2000
10005.053010006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.878610006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.593410006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.308710006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.133610006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.849310006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.562910006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.389810006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.103410006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.819010006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.532710006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.248310006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.964010006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.677610006.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.338210006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.623310006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.797810006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.083010006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.368210006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.653210006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.936310006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.221410006.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.936310007.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 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
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005998

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-

> <INCHI_KEY>
NNDIXBJHNLFJJP-DTLRTWKJSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.44345502523711

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid

> <ALOGPS_LOGP>
5.87

> <JCHEM_LOGP>
5.150492194333333

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.843936486031673

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771907472209

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9922622479596956

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.8827

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-hete

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005998
     RDKit          3D
20-Hydroxyeicosatetraenoic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
    7.8835    0.3581    0.1874 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3130    1.0473   -0.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8328    2.2904   -0.9930 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1411    0.5545   -1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.7504   -0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    0.0273    0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -1.4254    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1267   -2.2865    0.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612   -1.9175    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -2.4863    0.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515   -1.7621    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959   -0.2901    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    0.2455   -1.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0932    0.9822   -1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3191    1.3965   -0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4601    0.8630   -1.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3419    0.0411   -1.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3437   -0.4810    0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167   -0.0674    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8141   -0.6048    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1004   -0.2116    0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2269    1.2983    0.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2540    1.8809   -0.3039 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3452    2.8702   -0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0416    1.1318   -2.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2331   -0.5156   -1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7427    1.8362   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0461    0.3791   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7654    0.4019    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0130    0.3626    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9489   -1.8013   -0.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2865   -3.3828    0.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9017   -2.5073    2.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7427   -0.9053    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716   -3.6070    0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0435   -2.2117   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693    0.1611    0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    0.0043    0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -0.0139   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    1.3321   -2.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888    2.5436   -0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3137    1.1431    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692    1.1864   -2.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758   -0.3368   -1.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4491   -0.2605    0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3757   -1.6188    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -0.4720    1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6336    1.0466    0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7503   -1.7095    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8757   -0.1467   -0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9507   -0.5831    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1641   -0.6017    1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2045    1.5129    1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4581    1.7632    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8538    2.7962   -0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 29-MAR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-MAR-18         0                                  
HETATM    1  C   UNK     0    8676.0998679.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8677.6408679.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8678.9748678.522   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8680.3108679.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8681.8498679.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8683.1858678.522   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8684.5178679.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8686.0618679.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8687.3938678.522   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8688.7298679.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8690.0618678.522   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8691.3978679.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8692.7338678.522   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8694.0658679.290   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8674.7658678.522   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8673.4308679.290   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8671.8898679.290   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.5558678.522   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8669.2218679.290   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.8868678.522   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.5488679.290   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8665.2138678.522   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8666.5488680.831   0.000  0.00  0.00           O+0
CONECT    1    2   15                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    1   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   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0005998
HETATM    1  O1  UNL     1       7.883   0.358   0.187  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.313   1.047  -0.713  1.00  0.00           C  
HETATM    3  O2  UNL     1       7.833   2.290  -0.993  1.00  0.00           O  
HETATM    4  C2  UNL     1       6.141   0.555  -1.440  1.00  0.00           C  
HETATM    5  C3  UNL     1       4.831   0.750  -0.709  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.825   0.027   0.625  1.00  0.00           C  
HETATM    7  C5  UNL     1       5.007  -1.425   0.487  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.127  -2.287   0.910  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.861  -1.918   1.568  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.763  -2.486   0.744  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.851  -1.762   0.186  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.796  -0.290   0.298  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.851   0.246  -1.097  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.093   0.982  -1.588  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.319   1.396  -0.891  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.460   0.863  -1.683  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.342   0.041  -1.213  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.344  -0.481   0.162  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.617  -0.067   0.877  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.814  -0.605   0.170  1.00  0.00           C  
HETATM   21  C19 UNL     1      -7.100  -0.212   0.882  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.227   1.298   0.942  1.00  0.00           C  
HETATM   23  O3  UNL     1      -7.254   1.881  -0.304  1.00  0.00           O  
HETATM   24  H1  UNL     1       8.345   2.870  -0.343  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.042   1.132  -2.399  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.233  -0.516  -1.754  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.743   1.836  -0.490  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.046   0.379  -1.397  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.765   0.402   1.154  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.013   0.363   1.276  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.949  -1.801  -0.005  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.286  -3.383   0.796  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.902  -2.507   2.562  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.743  -0.905   1.901  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.772  -3.607   0.632  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.043  -2.212  -0.420  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.669   0.161   0.833  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.100   0.004   0.862  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.745  -0.014  -1.727  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.047   1.332  -2.646  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.389   2.544  -0.886  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.314   1.143   0.152  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.569   1.186  -2.747  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.176  -0.337  -1.853  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.449  -0.260   0.756  1.00  0.00           H  
HETATM   46  H23 UNL     1      -3.376  -1.619   0.074  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.593  -0.472   1.922  1.00  0.00           H  
HETATM   48  H25 UNL     1      -4.634   1.047   0.867  1.00  0.00           H  
HETATM   49  H26 UNL     1      -5.750  -1.710   0.146  1.00  0.00           H  
HETATM   50  H27 UNL     1      -5.876  -0.147  -0.847  1.00  0.00           H  
HETATM   51  H28 UNL     1      -7.951  -0.583   0.284  1.00  0.00           H  
HETATM   52  H29 UNL     1      -7.164  -0.602   1.902  1.00  0.00           H  
HETATM   53  H30 UNL     1      -8.204   1.513   1.447  1.00  0.00           H  
HETATM   54  H31 UNL     1      -6.458   1.763   1.593  1.00  0.00           H  
HETATM   55  H32 UNL     1      -6.854   2.796  -0.211  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8    8   31
CONECT    8    9   32
CONECT    9   10   33   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   37   38
CONECT   13   14   14   39
CONECT   14   15   40
CONECT   15   16   41   42
CONECT   16   17   17   43
CONECT   17   18   44
CONECT   18   19   45   46
CONECT   19   20   47   48
CONECT   20   21   49   50
CONECT   21   22   51   52
CONECT   22   23   53   54
CONECT   23   55
END

HMDB0005998
     RDKit          3D
20-Hydroxyeicosatetraenoic acid
 55 54  0  0  0  0  0  0  0  0999 V2000
    7.8835    0.3581    0.1874 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3130    1.0473   -0.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8328    2.2904   -0.9930 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1411    0.5545   -1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8313    0.7504   -0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    0.0273    0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -1.4254    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1267   -2.2865    0.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612   -1.9175    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -2.4863    0.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515   -1.7621    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959   -0.2901    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    0.2455   -1.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0932    0.9822   -1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3191    1.3965   -0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4601    0.8630   -1.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3419    0.0411   -1.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3437   -0.4810    0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167   -0.0674    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8141   -0.6048    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1004   -0.2116    0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2269    1.2983    0.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2540    1.8809   -0.3039 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3452    2.8702   -0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0416    1.1318   -2.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2331   -0.5156   -1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7427    1.8362   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0461    0.3791   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7654    0.4019    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0130    0.3626    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9489   -1.8013   -0.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2865   -3.3828    0.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9017   -2.5073    2.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7427   -0.9053    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716   -3.6070    0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0435   -2.2117   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693    0.1611    0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    0.0043    0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -0.0139   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    1.3321   -2.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888    2.5436   -0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3137    1.1431    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692    1.1864   -2.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758   -0.3368   -1.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4491   -0.2605    0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3757   -1.6188    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -0.4720    1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6336    1.0466    0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7503   -1.7095    0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8757   -0.1467   -0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9507   -0.5831    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1641   -0.6017    1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2045    1.5129    1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4581    1.7632    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8538    2.7962   -0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoic acid	ChEBI
20-Hydroxy arachidonic acid	ChEBI
20-Hydroxyarachidonic acid	ChEBI
20-Hydroxyicosatetraenoic acid	ChEBI
(5Z,8Z,11Z,14Z)-20-Hydroxyicosa-5,8,11,14-tetraenoate	Generator
20-Hydroxy arachidonate	Generator
20-Hydroxyarachidonate	Generator
20-Hydroxyicosatetraenoate	Generator
20-Hydroxyeicosatetraenoate	Generator
(all-Z)-20-Hydroxy-5,8,11,14-eicosatetraenoate	HMDB
(all-Z)-20-Hydroxy-5,8,11,14-eicosatetraenoic acid	HMDB
20-HETE	HMDB
20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate	HMDB
20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid	HMDB
20-Hydroxy-5,8,11,14-eicosatetraenoate	HMDB
20-Hydroxy-5,8,11,14-eicosatetraenoic acid	HMDB
20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate	HMDB
20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid	HMDB

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid

Traditional Name

20-hete

CAS Registry Number

79551-86-3

SMILES

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

InChI Identifier

InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-

InChI Key

NNDIXBJHNLFJJP-DTLRTWKJSA-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
Hydroxy 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
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:34306 )
HETE (CHEBI:34306 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C14748 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060009 )

Ontology

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	0.0012 g/L	ALOGPS
logP	5.87	ALOGPS
logP	5.15	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	101.88 m³·mol⁻¹	ChemAxon
Polarizability	38.44 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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]+	186.381	31661259
DarkChem	[M-H]-	190.99	31661259
DeepCCS	[M+H]+	187.731	30932474
DeepCCS	[M-H]-	185.373	30932474
DeepCCS	[M-2H]-	218.259	30932474
DeepCCS	[M+Na]+	193.824	30932474
AllCCS	[M+H]+	183.0	32859911
AllCCS	[M+H-H2O]+	180.1	32859911
AllCCS	[M+NH4]+	185.6	32859911
AllCCS	[M+Na]+	186.4	32859911
AllCCS	[M-H]-	185.2	32859911
AllCCS	[M+Na-2H]-	187.0	32859911
AllCCS	[M+HCOO]-	189.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.96 minutes	32390414
Predicted by Siyang on May 30, 2022	20.6864 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.25 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3032.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	372.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	264.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	652.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	973.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	537.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1988.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	676.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1724.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	726.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	479.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	409.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	432.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
20-Hydroxyeicosatetraenoic acid	OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	3964.3	Standard polar	33892256
20-Hydroxyeicosatetraenoic acid	OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	2217.4	Standard non polar	33892256
20-Hydroxyeicosatetraenoic acid	OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	2599.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
20-Hydroxyeicosatetraenoic acid,1TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O	2826.4	Semi standard non polar	33892256
20-Hydroxyeicosatetraenoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO	2608.4	Semi standard non polar	33892256
20-Hydroxyeicosatetraenoic acid,2TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2694.4	Semi standard non polar	33892256
20-Hydroxyeicosatetraenoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O	3045.0	Semi standard non polar	33892256
20-Hydroxyeicosatetraenoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO	2863.7	Semi standard non polar	33892256
20-Hydroxyeicosatetraenoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3184.2	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 - 20-Hydroxyeicosatetraenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-3290000000-c19c2446fd09c9b5b114	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-Hydroxyeicosatetraenoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0g6s-8958400000-372a8a263c8ea8f0e5b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-Hydroxyeicosatetraenoic 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 - 20-Hydroxyeicosatetraenoic acid 10V, Positive-QTOF	splash10-0uk9-0059000000-650b772489866747dfc1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Positive-QTOF	splash10-0pdr-2293000000-4135e55c1f638956a165	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Positive-QTOF	splash10-0006-8890000000-7333663b79a20dc52435	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 10V, Negative-QTOF	splash10-014i-0039000000-b8b23d059895b0d51482	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Negative-QTOF	splash10-0gb9-2098000000-7fd830563f4a43d0b812	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Negative-QTOF	splash10-0a4l-9040000000-ac722c9b6528d7965c21	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 10V, Negative-QTOF	splash10-014i-0009000000-c55e430e69fa5c79a747	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Negative-QTOF	splash10-0gb9-1049000000-1b54cbfba7d53b2e17ab	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Negative-QTOF	splash10-006x-9151000000-9d68be1fa8ed76d657d4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 10V, Positive-QTOF	splash10-0uk9-1229000000-2c09f1a1c932d016c5e4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 20V, Positive-QTOF	splash10-0fe1-5934000000-650155a4dedf606f2045	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxyeicosatetraenoic acid 40V, Positive-QTOF	splash10-00lu-7900000000-c13624e44921230c2908	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00301 +/- 0.00193 uM	Adult (>18 years old)	Not Specified	Normal	18953024	details
Blood	Detected and Quantified	0.0014 (0.00043-0.0053) uM	Adult (>18 years old)	Both	Normal	18378855	details
Blood	Detected and Quantified	0.00177 +/- 0.00043 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000917 +/- 0.00058 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.00083 +/- 0.00015 uM	Adult (>18 years old)	Both	Normal	20671299	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00037 +/- 0.00015 uM	Adult (>18 years old)	Both	Normal	John W. Newman, U...	details
Urine	Detected and Quantified	0.0001 +/- 0.000019 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	17462541	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0037 (0.0013-0.0059) uM	Adult (>18 years old)	Both	Renovascular disease	18378855	details
Blood	Detected and Quantified	0.0028 (0.0012-0.0067) uM	Adult (>18 years old)	Both	Hypertension	18378855	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.009 +/-0.23 uM	Adult (>18 years old)	Both	Cerebral Vasospasm	15910986	details
Urine	Detected and Quantified	0.0045 (0.0015-0.0087) umol/mmol creatinine	Adult (>18 years old)	Both	Renovascular disease	18378855	details

Associated Disorders and Diseases

Disease References

Hypertension
Minuz P, Jiang H, Fava C, Turolo L, Tacconelli S, Ricci M, Patrignani P, Morganti A, Lechi A, McGiff JC: Altered release of cytochrome p450 metabolites of arachidonic acid in renovascular disease. Hypertension. 2008 May;51(5):1379-85. doi: 10.1161/HYPERTENSIONAHA.107.105395. Epub 2008 Mar 31. [PubMed:18378855 ]
Cerebral vasospasm
Poloyac SM, Reynolds RB, Yonas H, Kerr ME: Identification and quantification of the hydroxyeicosatetraenoic acids, 20-HETE and 12-HETE, in the cerebrospinal fluid after subarachnoid hemorrhage. J Neurosci Methods. 2005 Jun 15;144(2):257-63. Epub 2004 Dec 30. [PubMed:15910986 ]

Associated OMIM IDs

145500 (Hypertension)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023796

KNApSAcK ID

Not Available

Chemspider ID

4446281

KEGG Compound ID

C14748

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

20-Hydroxyeicosatetraenoic acid

METLIN ID

Not Available

PubChem Compound

5283157

PDB ID

Not Available

ChEBI ID

34306

Food Biomarker Ontology

Not Available

VMH ID

WHARACHD

MarkerDB ID

MDB00000479

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Miyata N, Roman RJ: Role of 20-hydroxyeicosatetraenoic acid (20-HETE) in vascular system. J Smooth Muscle Res. 2005 Aug;41(4):175-93. [PubMed:16258232 ]

Enzymes

Enzyme Details

1. Cytochrome P450 4A11

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE).
Gene Name:: CYP4A11
Uniprot ID:: Q02928
Molecular weight:: 59347.31

Reactions

Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Water	details

Enzyme Details

2. Leukotriene-B(4) omega-hydroxylase 1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP4F2
Uniprot ID:: P78329
Molecular weight:: 59852.825

Reactions

Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Water	details

Enzyme Details

3. Leukotriene-B(4) omega-hydroxylase 2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. This enzyme requires molecular oxygen and NADPH for the omega-hydroxylation of LTB4, a potent chemoattractant for polymorphonuclear leukocytes.
Gene Name:: CYP4F3
Uniprot ID:: Q08477
Molecular weight:: 59846.085

Reactions

Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Water	details

Enzyme Details

4. Cytochrome P450 4F11

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Not Available
Gene Name:: CYP4F11
Uniprot ID:: Q9HBI6
Molecular weight:: 60145.165

Reactions

Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Water	details

Enzyme Details

5. Cytochrome P450 4F8

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Hydroxylates arachidonic acid (20:4n-6) to (18R)-hydroxyarachidonate. Shows little activity against prostaglandin (PG) D2, PGE1, PGE2, PGF2alpha, and leukotriene B4. Catalyzes omega-2 and omega-3-hydroxylation of PGH1 and PGH2. Catalyzes epoxidation of 4,7,10,13,16,19-(Z)-docosahexaenoic acid (22:6n-3) and 7,10,13,16,19-(Z)-docosapentaenoic acid (22:5n-3) and omega-3-hydroxylation of 4,7,10,13,16-(Z)-docosapentaenoic acid (22:5n-6). Catalyzes hydroxylation of PGI2 and carbaprostacyclin.
Gene Name:: CYP4F8
Uniprot ID:: P98187
Molecular weight:: 59993.995

Reactions

Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Water	details

Enzyme Details

6. Cytochrome P450 4A22

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate and palmitate. Shows no activity towards arachidonic acid and prostaglandin A1. Lacks functional activity in the kidney and does not contribute to renal 20-hydroxyeicosatetraenoic acid (20-HETE) biosynthesis.
Gene Name:: CYP4A22
Uniprot ID:: Q5TCH4
Molecular weight:: 59245.28

Reactions

Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Water	details

Enzyme Details

7. Cytochrome P450 4F22

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP4F22
Uniprot ID:: Q6NT55
Molecular weight:: Not Available

Reactions

Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 20-Hydroxyeicosatetraenoic acid + NADP + Water	details

Showing metabocard for 20-Hydroxyeicosatetraenoic acid (HMDB0005998)

MOL for HMDB0005998 (20-Hydroxyeicosatetraenoic acid)

3D MOL for HMDB0005998 (20-Hydroxyeicosatetraenoic acid)

3D SDF for HMDB0005998 (20-Hydroxyeicosatetraenoic acid)

3D-SDF for HMDB0005998 (20-Hydroxyeicosatetraenoic acid)

PDB for HMDB0005998 (20-Hydroxyeicosatetraenoic acid)

3D PDB for HMDB0005998 (20-Hydroxyeicosatetraenoic acid)

SMILES for HMDB0005998 (20-Hydroxyeicosatetraenoic acid)

INCHI for HMDB0005998 (20-Hydroxyeicosatetraenoic acid)

Structure for HMDB0005998 (20-Hydroxyeicosatetraenoic acid)

3D Structure for HMDB0005998 (20-Hydroxyeicosatetraenoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions