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Showing NP-Card for 15(S)-HPETE (NP0334110)

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Record Information
Version2.0
Created at2024-09-09 22:13:59 UTC
Updated at2024-09-09 22:14:02 UTC
NP-MRD IDNP0334110
Secondary Accession NumbersNone
Natural Product Identification
Common Name15(S)-HPETE
Description15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HPETE) is the corresponding hydroperoxide of 15(S)-HETE and undergoes homolytic decomposition to the DNA-reactive bifunctional electrophile 4-oxo-2(E)-nonenal, a precursor of heptanone-etheno-2'-deoxyguanosine. Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into (15-HPETE); vitamin C mediates 15(S)-HPETE decomposition. 15(S)-HPETE initiates apoptosis in vascular smooth muscle cells. 15(S)-HPETE is a lipoxygenase metabolite that affects the expression of cell adhesion molecules (CAMs) involved in the adhesion of leukocytes and/or the accumulation of leukocytes in the vascular endothelium, these being the initial events in endothelial cell injury. 15(S)-HPETE induces a loss of cardiomyocytes membrane integrity. 15-(S)HPETE is a hydroperoxide that enhances the activity of the enzymes lipoxygenase [EC 1.13.11.12] And Na+, K+-ATPase [EC 3.6.3.9] Of brain microvessels. Lipoxygenase(s) and Na+-K+-ATPase of brain microvessels may play a significant role in the occurrence of ischemic brain edema. (PMID: 15964853 , 15723435 , 8655602 , 8595608 , 2662983 ) [HMDB]
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334110 (15(S)-HPETE)


  Mrv1572004261605342D          

 33 32  0  0  1  0            999 V2000
    0.0000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9625    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    5.7158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    5.7158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    5.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  3  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 20  2  0  0  0  0
 22 20  1  0  0  0  0
 19 24  1  6  0  0  0
 24 23  1  0  0  0  0
 25  4  1  0  0  0  0
 26  5  1  0  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 29 10  1  0  0  0  0
 30 11  1  0  0  0  0
 31 14  1  0  0  0  0
 32 17  1  0  0  0  0
 19 33  1  6  0  0  0
M  END
Download

3D MOL for NP0334110 (15(S)-HPETE)

Download
3D SDF for NP0334110 (15(S)-HPETE)

  Mrv1572004261605342D          

 33 32  0  0  1  0            999 V2000
    0.0000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9625    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    5.7158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    5.7158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    5.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  3  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 20  2  0  0  0  0
 22 20  1  0  0  0  0
 19 24  1  6  0  0  0
 24 23  1  0  0  0  0
 25  4  1  0  0  0  0
 26  5  1  0  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 29 10  1  0  0  0  0
 30 11  1  0  0  0  0
 31 14  1  0  0  0  0
 32 17  1  0  0  0  0
 19 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334110

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4+,10-8+,11-9+,17-14+/t19-/m0/s1

> <INCHI_KEY>
BFWYTORDSFIVKP-IXNHTQMRSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.64879701822046

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5E,8E,11E,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid

> <ALOGPS_LOGP>
5.86

> <JCHEM_LOGP>
5.805695121333333

> <ALOGPS_LOGS>
-5.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712374063193028

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771784961381

> <JCHEM_PKA_STRONGEST_BASIC>
-4.236807609084836

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
102.81969999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E,8E,11E,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334110 (15(S)-HPETE)
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PDB for NP0334110 (15(S)-HPETE)
HEADER    PROTEIN                                 26-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-16         0                                  
HETATM    1  C   UNK     0       0.000   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.090   9.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.400   8.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.550   9.336   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.780   8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.710   9.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.240   8.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.470   6.668   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.020  10.669   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.930   6.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.790  12.003   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.330  12.003   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      23.100  13.337   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      23.100  10.669   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.930   4.001   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      13.090   6.668   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      13.860  10.669   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      15.400  10.669   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      11.550   6.668   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      18.480   8.002   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       8.470   9.336   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       9.240   5.335   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.160   8.002   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.390   6.668   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2   13                                                       
CONECT    4    5    6   25                                                  
CONECT    5    4    7   26                                                  
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10   27                                                  
CONECT    9    7   11   28                                                  
CONECT   10    8   12   29                                                  
CONECT   11    9   14   30                                                  
CONECT   12   10   15                                                       
CONECT   13    3   16                                                       
CONECT   14   11   17   31                                                  
CONECT   15   12   18                                                       
CONECT   16   13   19                                                       
CONECT   17   14   19   32                                                  
CONECT   18   15   20                                                       
CONECT   19   16   17   24   33                                             
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   24                                                            
CONECT   24   19   23                                                       
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   14                                                            
CONECT   32   17                                                            
CONECT   33   19                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   64    0
END

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3D PDB for NP0334110 (15(S)-HPETE)
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SMILES for NP0334110 (15(S)-HPETE)
[H]\C(CCCC(O)=O)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])\C(\[H])=C(/[H])[C@]([H])(CCCCC)OO
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INCHI for NP0334110 (15(S)-HPETE)
InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4+,10-8+,11-9+,17-14+/t19-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H32O4
Average Mass336.4720 Da
Monoisotopic Mass336.23006 Da
IUPAC Name(5E,8E,11E,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
Traditional Name(5E,8E,11E,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCC(O)=O)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])\C(\[H])=C(/[H])[C@]([H])(CCCCC)OO
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4+,10-8+,11-9+,17-14+/t19-/m0/s1
InChI KeyBFWYTORDSFIVKP-IXNHTQMRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassEicosanoids  
Direct ParentHydroperoxyeicosatetraenoic acids  
Alternative Parents
Substituents
  • Hydroperoxyeicosatetraenoic acid
    • 

  • Long-chain fatty acid
    • 

  • Hydroperoxy fatty acid
    • 

  • Fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Allylic hydroperoxide
    • 

  • Hydroperoxide
    • 

  • Alkyl hydroperoxide
    • 

  • Peroxol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.86ALOGPS
logP5.81ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity102.82 m³·mol⁻¹ChemAxon
Polarizability39.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6505405  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lee SH, Williams MV, Dubois RN, Blair IA: Cyclooxygenase-2-mediated DNA damage. J Biol Chem. 2005 Aug 5;280(31):28337-46. doi: 10.1074/jbc.M504178200. Epub 2005  Jun 17. [PubMed:15964853  ] 
  2. Williams MV, Lee SH, Blair IA: Liquid chromatography/mass spectrometry analysis of bifunctional electrophiles and DNA adducts from vitamin C mediated decomposition of 15-hydroperoxyeicosatetraenoic acid. Rapid Commun Mass Spectrom. 2005;19(6):849-58. doi: 10.1002/rcm.1854. [PubMed:15723435  ] 
  3. Sultana C, Shen Y, Rattan V, Kalra VK: Lipoxygenase metabolites induced expression of adhesion molecules and transendothelial migration of monocyte-like HL-60 cells is linked to protein kinase C activation. J Cell Physiol. 1996 Jun;167(3):477-87. doi: 10.1002/(SICI)1097-4652(199606)167:3<477::AID-JCP12>3.0.CO;2-1. [PubMed:8655602  ] 
  4. Thollon C, Iliou JP, Cambarrat C, Robin F, Vilaine JP: Nature of the cardiomyocyte injury induced by lipid hydroperoxides. Cardiovasc Res. 1995 Nov;30(5):648-55. [PubMed:8595608  ] 
  5. Asano T, Koide T, Gotoh O, Joshita H, Hanamura T, Shigeno T, Takakura K: The role of free radicals and eicosanoids in the pathogenetic mechanism underlying ischemic brain edema. Mol Chem Neuropathol. 1989 Apr;10(2):101-33. doi: 10.1007/BF03159717. [PubMed:2662983  ]