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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 15:07:35 UTC

Update Date

2022-03-07 02:49:20 UTC

HMDB ID

HMDB0004244

Secondary Accession Numbers

HMDB0006501
HMDB04244
HMDB06501

Metabolite Identification

Common Name

15(S)-HPETE

Description

15(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 ).

Structure

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

HMDB0004244
     RDKit          3D
15(S)-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -6.7466   -0.5292    3.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694    0.3191    2.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5624   -0.3817    1.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6341    0.3780    1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1393    0.6848   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4849   -0.4861   -1.2189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3944   -1.4157   -1.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974   -1.1340   -1.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860   -2.1093   -1.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.8579   -1.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7127   -0.5189   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997    0.0360   -2.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586    0.3461   -2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079    0.1748   -1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9821    1.5206   -0.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2270    1.8575   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3244    0.9110   -0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1369    0.7276    0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4276    0.1828    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3229    0.9990    2.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722    0.5066    2.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5185    2.3166    2.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5661   -1.1586   -0.6178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6751   -1.0622   -1.2800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7298   -0.7347    2.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2282   -1.4965    3.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9398   -0.0453    4.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6651    1.2681    2.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4118    0.6421    1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7757   -1.4172    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0202   -0.5008    2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4754    1.3782    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520   -0.1349    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4123    1.3804   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0793    1.3034   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9337   -0.0524   -2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6595   -2.4428   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8579   -0.1234   -1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764   -3.1235   -2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -2.6846   -2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2539   -0.6264   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.2201   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    0.1804   -3.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196    0.7590   -3.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678   -0.2327   -0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567   -0.5233   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    2.2772   -0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304    2.8750   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0783    1.4395   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055   -0.0206   -1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0170    0.0470    0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6322    1.7101    0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2085    0.0659    2.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1001   -0.8908    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1455    2.4858    3.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8471   -1.8869   -1.7721 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  6 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  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 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 02231219552D          

 24 23  0  0  1  0            999 V2000
   25.7958  -10.2641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5102  -10.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7958  -15.2142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5102  -13.9767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7958   -9.4391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.5102   -9.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2247   -9.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9392   -9.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0812  -13.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6537   -9.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0812  -13.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3668  -12.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9378  -11.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9378  -10.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3682   -9.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7958  -14.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6523  -13.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9378  -12.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2233  -11.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2233  -10.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0812   -9.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9378   -9.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3668   -9.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6523   -9.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  5  1  1  6  0  0  0
  3 16  1  0  0  0  0
  4 16  2  0  0  0  0
  5  6  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 20  1  0  0  0  0
 14 22  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  2  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004244

> <DATABASE_NAME>
hmdb

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

> <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-VAEKSGALSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.422233971583424

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z,11Z,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>
66.75999999999999

> <JCHEM_REFRACTIVITY>
102.81970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15(S)-hpete

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004244
     RDKit          3D
15(S)-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -6.7466   -0.5292    3.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694    0.3191    2.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5624   -0.3817    1.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6341    0.3780    1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1393    0.6848   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4849   -0.4861   -1.2189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3944   -1.4157   -1.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974   -1.1340   -1.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860   -2.1093   -1.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.8579   -1.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7127   -0.5189   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997    0.0360   -2.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586    0.3461   -2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079    0.1748   -1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9821    1.5206   -0.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2270    1.8575   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3244    0.9110   -0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1369    0.7276    0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4276    0.1828    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3229    0.9990    2.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722    0.5066    2.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5185    2.3166    2.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5661   -1.1586   -0.6178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6751   -1.0622   -1.2800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7298   -0.7347    2.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2282   -1.4965    3.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9398   -0.0453    4.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6651    1.2681    2.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4118    0.6421    1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7757   -1.4172    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0202   -0.5008    2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4754    1.3782    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520   -0.1349    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4123    1.3804   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0793    1.3034   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9337   -0.0524   -2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6595   -2.4428   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8579   -0.1234   -1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764   -3.1235   -2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -2.6846   -2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2539   -0.6264   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.2201   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    0.1804   -3.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196    0.7590   -3.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678   -0.2327   -0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567   -0.5233   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    2.2772   -0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304    2.8750   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0783    1.4395   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055   -0.0206   -1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0170    0.0470    0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6322    1.7101    0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2085    0.0659    2.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1001   -0.8908    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1455    2.4858    3.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8471   -1.8869   -1.7721 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  6 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  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 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  O   UNK     0      48.152 -19.160   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      49.486 -19.930   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      48.152 -28.400   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      49.486 -26.090   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      48.152 -17.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      49.486 -16.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      50.819 -17.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      52.153 -16.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      46.818 -24.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      53.487 -17.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      46.818 -26.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.485 -23.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.817 -22.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      42.817 -19.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      54.821 -16.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      48.152 -26.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      44.151 -24.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      42.817 -23.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.483 -21.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.483 -19.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      46.818 -16.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.817 -17.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.485 -17.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      44.151 -16.850   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5    1    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   10                                                       
CONECT    9   11   12                                                       
CONECT   10    8   15                                                       
CONECT   11    9   16                                                       
CONECT   12    9   17                                                       
CONECT   13   18   19                                                       
CONECT   14   20   22                                                       
CONECT   15   10                                                            
CONECT   16    3    4   11                                                  
CONECT   17   12   18                                                       
CONECT   18   13   17                                                       
CONECT   19   13   20                                                       
CONECT   20   14   19                                                       
CONECT   21    5   23                                                       
CONECT   22   14   24                                                       
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0004244
HETATM    1  C1  UNL     1      -6.747  -0.529   3.062  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.869   0.319   2.155  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.562  -0.382   1.886  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.634   0.378   1.001  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.139   0.685  -0.364  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.485  -0.486  -1.219  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.394  -1.416  -1.506  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.097  -1.134  -1.494  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.086  -2.109  -1.788  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.179  -1.858  -1.774  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.713  -0.519  -1.444  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.500   0.036  -2.561  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.759   0.346  -2.428  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.508   0.175  -1.170  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.982   1.521  -0.762  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.227   1.858  -0.603  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.324   0.911  -0.820  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.137   0.728   0.429  1.00  0.00           C  
HETATM   19  C19 UNL     1       6.428   0.183   1.620  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.323   0.999   2.120  1.00  0.00           C  
HETATM   21  O1  UNL     1       4.172   0.507   2.212  1.00  0.00           O  
HETATM   22  O2  UNL     1       5.519   2.317   2.498  1.00  0.00           O  
HETATM   23  O3  UNL     1      -5.566  -1.159  -0.618  1.00  0.00           O  
HETATM   24  O4  UNL     1      -6.675  -1.062  -1.280  1.00  0.00           O  
HETATM   25  H1  UNL     1      -7.730  -0.735   2.579  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.228  -1.496   3.321  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.940  -0.045   4.044  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.665   1.268   2.733  1.00  0.00           H  
HETATM   29  H5  UNL     1      -6.412   0.642   1.253  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.776  -1.417   1.560  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.020  -0.501   2.872  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.475   1.378   1.506  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.652  -0.135   0.974  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.412   1.380  -0.847  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.079   1.303  -0.274  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.934  -0.052  -2.165  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.659  -2.443  -1.754  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.858  -0.123  -1.256  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.476  -3.123  -2.036  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.868  -2.685  -2.017  1.00  0.00           H  
HETATM   41  H17 UNL     1       1.254  -0.626  -0.487  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.102   0.220  -1.186  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.964   0.180  -3.530  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.320   0.759  -3.279  1.00  0.00           H  
HETATM   45  H21 UNL     1       2.968  -0.233  -0.317  1.00  0.00           H  
HETATM   46  H22 UNL     1       4.357  -0.523  -1.442  1.00  0.00           H  
HETATM   47  H23 UNL     1       3.204   2.277  -0.584  1.00  0.00           H  
HETATM   48  H24 UNL     1       5.530   2.875  -0.295  1.00  0.00           H  
HETATM   49  H25 UNL     1       7.078   1.440  -1.538  1.00  0.00           H  
HETATM   50  H26 UNL     1       6.106  -0.021  -1.332  1.00  0.00           H  
HETATM   51  H27 UNL     1       8.017   0.047   0.241  1.00  0.00           H  
HETATM   52  H28 UNL     1       7.632   1.710   0.703  1.00  0.00           H  
HETATM   53  H29 UNL     1       7.208   0.066   2.437  1.00  0.00           H  
HETATM   54  H30 UNL     1       6.100  -0.891   1.436  1.00  0.00           H  
HETATM   55  H31 UNL     1       6.146   2.486   3.301  1.00  0.00           H  
HETATM   56  H32 UNL     1      -6.847  -1.887  -1.772  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   23   36
CONECT    7    8    8   37
CONECT    8    9   38
CONECT    9   10   10   39
CONECT   10   11   40
CONECT   11   12   41   42
CONECT   12   13   13   43
CONECT   13   14   44
CONECT   14   15   45   46
CONECT   15   16   16   47
CONECT   16   17   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

HMDB0004244
     RDKit          3D
15(S)-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -6.7466   -0.5292    3.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694    0.3191    2.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5624   -0.3817    1.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6341    0.3780    1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1393    0.6848   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4849   -0.4861   -1.2189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3944   -1.4157   -1.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974   -1.1340   -1.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0860   -2.1093   -1.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.8579   -1.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7127   -0.5189   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997    0.0360   -2.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586    0.3461   -2.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079    0.1748   -1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9821    1.5206   -0.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2270    1.8575   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3244    0.9110   -0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1369    0.7276    0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4276    0.1828    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3229    0.9990    2.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722    0.5066    2.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5185    2.3166    2.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5661   -1.1586   -0.6178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6751   -1.0622   -1.2800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7298   -0.7347    2.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2282   -1.4965    3.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9398   -0.0453    4.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6651    1.2681    2.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4118    0.6421    1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7757   -1.4172    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0202   -0.5008    2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4754    1.3782    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520   -0.1349    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4123    1.3804   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0793    1.3034   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9337   -0.0524   -2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6595   -2.4428   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8579   -0.1234   -1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764   -3.1235   -2.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -2.6846   -2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2539   -0.6264   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.2201   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    0.1804   -3.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196    0.7590   -3.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678   -0.2327   -0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567   -0.5233   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    2.2772   -0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304    2.8750   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0783    1.4395   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055   -0.0206   -1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0170    0.0470    0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6322    1.7101    0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2085    0.0659    2.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1001   -0.8908    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1455    2.4858    3.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8471   -1.8869   -1.7721 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  6 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  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 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
(5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoate	ChEBI
(5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid	ChEBI
15-Hydroperoxyeicosatetraenoate	ChEBI
15-Hydroperoxyeicosatetraenoic acid	ChEBI
15-Hydroperoxyicosatetraenoate	ChEBI
15-Hydroperoxyicosatetraenoic acid	ChEBI
15S-HpETE	ChEBI
(5Z,8Z,11Z,13E,15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid	ChEBI, HMDB
(5Z,8Z,11Z,13E,15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoate	Generator, HMDB
15S-Hydroperoxyeicosatetraenoate	HMDB
15S-Hydroperoxyeicosatetraenoic acid	HMDB
14,15-Epoxyarachidonic acid	MeSH, HMDB
15-HPEA	MeSH, HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (Z,Z,Z,Z)-isomer	MeSH, HMDB
15-Hydroperoxyarachidonic acid	MeSH, HMDB
15-HPAA	MeSH, HMDB
15-HPETE	MeSH, HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid	MeSH, HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (e,Z,Z,Z)-isomer	MeSH, HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer	MeSH, HMDB
15-Hydroperoxy-5,8,11,14-eicosatetraenoic acid	MeSH, HMDB
Arachidonic acid 15-hydroperoxide	MeSH, HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid

Traditional Name

15(S)-hpete

CAS Registry Number

70981-96-3

SMILES

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

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-VAEKSGALSA-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:15628 )
Hydroperoxy fatty acids (C05966 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C05966 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060014 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0004244)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0004244)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0120510)

Metabolic pathway

Arachidonic Acid Metabolism (PathBank: SMP0087315)

Drug action pathway

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

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	0.0018 g/L	ALOGPS
logP	5.86	ALOGPS
logP	5.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.82	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	38.42 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]+	191.049	31661259
DarkChem	[M-H]-	190.297	31661259
DeepCCS	[M+H]+	190.106	30932474
DeepCCS	[M-H]-	187.748	30932474
DeepCCS	[M-2H]-	220.634	30932474
DeepCCS	[M+Na]+	196.199	30932474
AllCCS	[M+H]+	190.4	32859911
AllCCS	[M+H-H2O]+	187.6	32859911
AllCCS	[M+NH4]+	193.0	32859911
AllCCS	[M+Na]+	193.8	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
15(S)-HPETE	CCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O	4175.9	Standard polar	33892256
15(S)-HPETE	CCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O	2411.1	Standard non polar	33892256
15(S)-HPETE	CCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O	2671.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
15(S)-HPETE,1TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)OO	2758.5	Semi standard non polar	33892256
15(S)-HPETE,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)OO	2997.3	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 - 15(S)-HPETE GC-MS (Non-derivatized) - 70eV, Positive	splash10-0296-7691000000-10e52eac953fb64dc1a6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15(S)-HPETE GC-MS (1 TMS) - 70eV, Positive	splash10-00vr-9343000000-559ae101ce63837aa2c6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15(S)-HPETE GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15(S)-HPETE 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 - 15(S)-HPETE 10V, Positive-QTOF	splash10-014i-0129000000-35e1b05b3a271d79d7fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 20V, Positive-QTOF	splash10-066u-3494000000-dfe60ca573a64c813441	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 40V, Positive-QTOF	splash10-0abc-9650000000-4e66ed45e98b64d54b28	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 10V, Negative-QTOF	splash10-000i-0019000000-21ceecb44bdf804c0c4b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 20V, Negative-QTOF	splash10-01bi-3189000000-29f754a5638ca1b0ae57	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 40V, Negative-QTOF	splash10-0a4l-9150000000-81504e73ce15d31bbd08	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 10V, Negative-QTOF	splash10-0f79-0019000000-b91b825f9248bd953b5b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 20V, Negative-QTOF	splash10-0udi-0059000000-c3891e970dfe8176e4a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 40V, Negative-QTOF	splash10-0002-8091000000-62e6f1d45410fc34c98c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 10V, Positive-QTOF	splash10-0udr-0359000000-aaf43f18f05b65e0a949	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 20V, Positive-QTOF	splash10-0f79-1896000000-b6c85b7e90a53a2752ab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15(S)-HPETE 40V, Positive-QTOF	splash10-00l6-9810000000-898d59f193fb8d513678	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

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	0.00106 +/- 0.00041 uM	Adult (>18 years old)	Both	Normal	21359215	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444416

KEGG Compound ID

C05966

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280893

PDB ID

Not Available

ChEBI ID

15628

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Dussault, Patrick; Lee, In Quen. The total synthesis of 15(S)-HPETE (hydroperoxyeicosatetraenoic acid). Journal of Organic Chemistry (1992), 57(7), 1952-4.

Material Safety Data Sheet (MSDS)

Not Available

General References

Kuitert LM, Newton R, Barnes NC, Adcock IM, Barnes PJ: Eicosanoid mediator expression in mononuclear and polymorphonuclear cells in normal subjects and patients with atopic asthma and cystic fibrosis. Thorax. 1996 Dec;51(12):1223-8. [PubMed:8994519 ]
Terao J, Nagao A, Yuki H, Itoh Y: Reduction of fatty acid hydroperoxides by human parotid saliva. Lipids. 1993 Feb;28(2):121-4. [PubMed:8441337 ]
Lee SH, Williams MV, Dubois RN, Blair IA: Cyclooxygenase-2-mediated DNA damage. J Biol Chem. 2005 Aug 5;280(31):28337-46. Epub 2005 Jun 17. [PubMed:15964853 ]
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. [PubMed:15723435 ]
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. [PubMed:8655602 ]
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 ]
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. [PubMed:2662983 ]

Only showing the first 10 proteins. There are 33 proteins in total.

Show all enzymes and transporters

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 + 15(S)-HPETE → Oxidized glutathione + 15-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 + 15(S)-HPETE → Oxidized glutathione + 15-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 + 15(S)-HPETE → Oxidized glutathione + 15-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 + 15(S)-HPETE → Oxidized glutathione + 15-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 + 15(S)-HPETE → Oxidized glutathione + 15-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 + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Water	details

Enzyme Details

8. Arachidonate 15-lipoxygenase B

General function:: Involved in metal ion binding
Specific function:: Converts arachidonic acid exclusively to 15S-hydroperoxyeicosatetraenoic acid, while linoleic acid is less well metabolized.
Gene Name:: ALOX15B
Uniprot ID:: O15296
Molecular weight:: 72522.25

Reactions

Arachidonic acid + Oxygen → 15(S)-HPETE	details

Enzyme Details

9. Arachidonate 15-lipoxygenase

General function:: Involved in metal ion binding
Specific function:: Converts arachidonic acid to 15S-hydroperoxyeicosatetraenoic acid. Also acts on C-12 of arachidonate as well as on linoleic acid.
Gene Name:: ALOX15
Uniprot ID:: P16050
Molecular weight:: 74803.795

Reactions

Arachidonic acid + Oxygen → 15(S)-HPETE	details

Enzyme Details

10. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Only showing the first 10 proteins. There are 33 proteins in total.

Show all enzymes and transporters

Showing metabocard for 15(S)-HPETE (HMDB0004244)

MOL for HMDB0004244 (15(S)-HPETE)

3D MOL for HMDB0004244 (15(S)-HPETE)

3D SDF for HMDB0004244 (15(S)-HPETE)

3D-SDF for HMDB0004244 (15(S)-HPETE)

PDB for HMDB0004244 (15(S)-HPETE)

3D PDB for HMDB0004244 (15(S)-HPETE)

SMILES for HMDB0004244 (15(S)-HPETE)

INCHI for HMDB0004244 (15(S)-HPETE)

Structure for HMDB0004244 (15(S)-HPETE)

3D Structure for HMDB0004244 (15(S)-HPETE)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

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Reactions