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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-14 00:50:13 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004699

Secondary Accession Numbers

HMDB04699

Metabolite Identification

Common Name

8(S)-HPETE

Description

8(S)-HPETE, also known as 8-HPETE, 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. Thus, 8(S)-hpete is considered to be an eicosanoid. Based on a literature review very few articles have been published on 8(S)-HPETE.

Structure

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

HMDB0004699
     RDKit          3D
8(S)-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -9.5332   -0.7128    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2392   -0.5305    0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2179   -1.5413    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9628   -1.3862    1.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2826   -0.0503    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9091    0.2845   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6484    0.4783   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993    0.3972    0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    1.6858    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5052    1.7974    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990    0.6838   -0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5858    0.8759   -0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3773   -0.2859   -1.1072 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7420    0.2224   -1.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393    0.8794   -0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5960    0.4983   -0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3451   -0.6462   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6988   -0.1970   -1.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5324    0.4466   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7810   -0.4832    1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6484   -1.3835    0.9870 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0585   -0.3795    2.3126 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -0.9980   -2.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -2.2214   -1.7087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4046   -1.6228   -0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3739   -0.8735    0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6907    0.1929   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4463   -0.6889    2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8652    0.5091    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0373   -1.4947   -0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6313   -2.5510    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657   -1.5157    2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2131   -2.1859    1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0597    0.7293    1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4976    0.0848    1.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7082    0.3695   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187    0.7267   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467   -0.4242   -0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    0.0796    1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821    2.5826    0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    2.7821    0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -0.2975   -0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733    1.8780   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157   -0.9596   -0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2454   -0.6051   -2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4964    0.9603   -2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267    1.7642   -0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0066    1.0994    0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5767   -1.3381    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8507   -1.2467   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5165    0.5831   -1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2315   -1.0197   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9867    1.3531    0.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4824    0.7774   -0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8846    0.5407    2.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1047   -2.8621   -2.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  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
 13 23  1  0
 23 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  1
 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 02231219582D          
 
 24 23  0  0  1  0            999 V2000
   15.0024  -14.1048    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8233  -14.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2888  -14.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5369  -14.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5793  -14.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2505  -14.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7544  -14.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0714  -14.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0490  -14.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7849  -14.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3312  -14.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4944  -14.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6176  -14.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3194  -14.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9081  -14.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0329  -13.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1946  -14.5173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9081  -13.2838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7425  -14.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4561  -13.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1656  -14.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8792  -13.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7914  -13.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0056  -13.0053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 23  1  6  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004699

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
QQUFCXFFOZDXLA-VYOQERLCSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.52600864818525

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8S,9E,11Z,14Z)-8-hydroperoxyicosa-5,9,11,14-tetraenoic acid

> <ALOGPS_LOGP>
5.91

> <JCHEM_LOGP>
5.805695121333333

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.71107422095279

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.390349853072395

> <JCHEM_PKA_STRONGEST_BASIC>
-4.237376144832223

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
102.81969999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8S-HpETE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004699
     RDKit          3D
8(S)-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -9.5332   -0.7128    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2392   -0.5305    0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2179   -1.5413    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9628   -1.3862    1.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2826   -0.0503    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9091    0.2845   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6484    0.4783   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993    0.3972    0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    1.6858    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5052    1.7974    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990    0.6838   -0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5858    0.8759   -0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3773   -0.2859   -1.1072 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7420    0.2224   -1.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393    0.8794   -0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5960    0.4983   -0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3451   -0.6462   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6988   -0.1970   -1.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5324    0.4466   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7810   -0.4832    1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6484   -1.3835    0.9870 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0585   -0.3795    2.3126 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -0.9980   -2.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -2.2214   -1.7087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4046   -1.6228   -0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3739   -0.8735    0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6907    0.1929   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4463   -0.6889    2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8652    0.5091    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0373   -1.4947   -0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6313   -2.5510    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657   -1.5157    2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2131   -2.1859    1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0597    0.7293    1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4976    0.0848    1.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7082    0.3695   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187    0.7267   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467   -0.4242   -0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    0.0796    1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821    2.5826    0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    2.7821    0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -0.2975   -0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733    1.8780   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157   -0.9596   -0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2454   -0.6051   -2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4964    0.9603   -2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267    1.7642   -0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0066    1.0994    0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5767   -1.3381    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8507   -1.2467   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5165    0.5831   -1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2315   -1.0197   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9867    1.3531    0.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4824    0.7774   -0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8846    0.5407    2.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1047   -2.8621   -2.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  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
 13 23  1  0
 23 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  1
 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    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      28.004 -26.329   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.537 -27.097   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.672 -27.099   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.869 -26.331   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.348 -26.329   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.201 -27.097   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.808 -26.329   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.733 -27.097   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.491 -27.099   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.065 -26.177   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.152 -26.329   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.390 -27.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.820 -27.099   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.930 -27.020   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.495 -26.329   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      39.261 -26.101   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      17.163 -27.099   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      18.495 -24.796   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      40.586 -26.943   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.918 -26.101   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      43.242 -26.943   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      44.575 -26.101   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      27.611 -24.706   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      26.144 -24.277   0.000  0.00  0.00           O+0
CONECT    1    2    3   23                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17   18                                                  
CONECT   16   14   19                                                       
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23    1   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0004699
HETATM    1  C1  UNL     1      -9.533  -0.713   0.142  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.239  -0.531   0.949  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.218  -1.541   0.503  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.963  -1.386   1.300  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.283  -0.050   1.191  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.909   0.285  -0.193  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.648   0.478  -0.501  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.499   0.397   0.415  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.770   1.686   0.490  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.505   1.797   0.159  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.299   0.684  -0.310  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.586   0.876  -0.632  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.377  -0.286  -1.107  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.742   0.222  -1.607  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.439   0.879  -0.509  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.596   0.498  -0.045  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.345  -0.646  -0.575  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.699  -0.197  -1.101  1.00  0.00           C  
HETATM   19  C19 UNL     1       8.532   0.447  -0.003  1.00  0.00           C  
HETATM   20  C20 UNL     1       8.781  -0.483   1.108  1.00  0.00           C  
HETATM   21  O1  UNL     1       9.648  -1.383   0.987  1.00  0.00           O  
HETATM   22  O2  UNL     1       8.059  -0.380   2.313  1.00  0.00           O  
HETATM   23  O3  UNL     1       1.725  -0.998  -2.110  1.00  0.00           O  
HETATM   24  O4  UNL     1       1.481  -2.221  -1.709  1.00  0.00           O  
HETATM   25  H1  UNL     1      -9.405  -1.623  -0.477  1.00  0.00           H  
HETATM   26  H2  UNL     1     -10.374  -0.874   0.861  1.00  0.00           H  
HETATM   27  H3  UNL     1      -9.691   0.193  -0.451  1.00  0.00           H  
HETATM   28  H4  UNL     1      -8.446  -0.689   2.026  1.00  0.00           H  
HETATM   29  H5  UNL     1      -7.865   0.509   0.812  1.00  0.00           H  
HETATM   30  H6  UNL     1      -7.037  -1.495  -0.596  1.00  0.00           H  
HETATM   31  H7  UNL     1      -7.631  -2.551   0.771  1.00  0.00           H  
HETATM   32  H8  UNL     1      -6.266  -1.516   2.383  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.213  -2.186   1.040  1.00  0.00           H  
HETATM   34  H10 UNL     1      -6.060   0.729   1.489  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.498   0.085   1.937  1.00  0.00           H  
HETATM   36  H12 UNL     1      -5.708   0.370  -0.964  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.419   0.727  -1.545  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.847  -0.424  -0.006  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.702   0.080   1.437  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.282   2.583   0.829  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.020   2.782   0.236  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.077  -0.297  -0.414  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.973   1.878  -0.527  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.516  -0.960  -0.243  1.00  0.00           H  
HETATM   45  H21 UNL     1       4.245  -0.605  -2.111  1.00  0.00           H  
HETATM   46  H22 UNL     1       3.496   0.960  -2.425  1.00  0.00           H  
HETATM   47  H23 UNL     1       3.927   1.764  -0.055  1.00  0.00           H  
HETATM   48  H24 UNL     1       6.007   1.099   0.799  1.00  0.00           H  
HETATM   49  H25 UNL     1       6.577  -1.338   0.302  1.00  0.00           H  
HETATM   50  H26 UNL     1       5.851  -1.247  -1.333  1.00  0.00           H  
HETATM   51  H27 UNL     1       7.516   0.583  -1.860  1.00  0.00           H  
HETATM   52  H28 UNL     1       8.232  -1.020  -1.573  1.00  0.00           H  
HETATM   53  H29 UNL     1       7.987   1.353   0.381  1.00  0.00           H  
HETATM   54  H30 UNL     1       9.482   0.777  -0.461  1.00  0.00           H  
HETATM   55  H31 UNL     1       7.885   0.541   2.716  1.00  0.00           H  
HETATM   56  H32 UNL     1       2.105  -2.862  -2.134  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7   36
CONECT    7    8   37
CONECT    8    9   38   39
CONECT    9   10   10   40
CONECT   10   11   41
CONECT   11   12   12   42
CONECT   12   13   43
CONECT   13   14   23   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

HMDB0004699
     RDKit          3D
8(S)-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -9.5332   -0.7128    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2392   -0.5305    0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2179   -1.5413    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9628   -1.3862    1.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2826   -0.0503    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9091    0.2845   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6484    0.4783   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993    0.3972    0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702    1.6858    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5052    1.7974    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990    0.6838   -0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5858    0.8759   -0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3773   -0.2859   -1.1072 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7420    0.2224   -1.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393    0.8794   -0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5960    0.4983   -0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3451   -0.6462   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6988   -0.1970   -1.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5324    0.4466   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7810   -0.4832    1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6484   -1.3835    0.9870 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0585   -0.3795    2.3126 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -0.9980   -2.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -2.2214   -1.7087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4046   -1.6228   -0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3739   -0.8735    0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6907    0.1929   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4463   -0.6889    2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8652    0.5091    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0373   -1.4947   -0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6313   -2.5510    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657   -1.5157    2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2131   -2.1859    1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0597    0.7293    1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4976    0.0848    1.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7082    0.3695   -0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187    0.7267   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467   -0.4242   -0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    0.0796    1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821    2.5826    0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    2.7821    0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -0.2975   -0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733    1.8780   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157   -0.9596   -0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2454   -0.6051   -2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4964    0.9603   -2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267    1.7642   -0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0066    1.0994    0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5767   -1.3381    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8507   -1.2467   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5165    0.5831   -1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2315   -1.0197   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9867    1.3531    0.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4824    0.7774   -0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8846    0.5407    2.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1047   -2.8621   -2.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  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
 13 23  1  0
 23 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  1
 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,9E,11Z,14Z)-(8S)-8-Hydroperoxyeicosa-5,9,11,14-tetraenoic acid	ChEBI
(5Z,9E,11Z,14Z)-(8S)-8-Hydroperoxyicosa-5,9,11,14-tetraenoic acid	ChEBI
(5Z,9E,11Z,14Z)-(8S)-8-Hydroperoxyeicosa-5,9,11,14-tetraenoate	Generator
(5Z,9E,11Z,14Z)-(8S)-8-Hydroperoxyicosa-5,9,11,14-tetraenoate	Generator
8-HPETE	HMDB
8-Hydroperoxyeicosatetraenoic acid	HMDB
8-Peroxy-5Z,9E,11Z,14Z-eicosatetraenoate	HMDB
8-Peroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid	HMDB
8S-HpETE	HMDB
8S-Hydoperoxy-5Z,9E,11Z,14Z-eicosatetraenoate	HMDB
8S-Hydoperoxy-5Z,9E,11Z,14Z-eicosatetraenoic acid	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(5Z,8S,9E,11Z,14Z)-8-hydroperoxyicosa-5,9,11,14-tetraenoic acid

Traditional Name

8S-HpETE

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

QQUFCXFFOZDXLA-VYOQERLCSA-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:34487 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C14823 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060073 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0004699)
Membrane (HMDB: HMDB0004699)

Source

Exogenous

Exogenous (HMDB: HMDB0004699)

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: HMDB0004699)

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	0.0017 g/L	ALOGPS
logP	5.91	ALOGPS
logP	5.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	102.82 m³·mol⁻¹	ChemAxon
Polarizability	39.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	193.183	31661259
DarkChem	[M-H]-	191.553	31661259
DeepCCS	[M+H]+	190.033	30932474
DeepCCS	[M-H]-	187.675	30932474
DeepCCS	[M-2H]-	220.862	30932474
DeepCCS	[M+Na]+	196.126	30932474
AllCCS	[M+H]+	190.6	32859911
AllCCS	[M+H-H2O]+	187.8	32859911
AllCCS	[M+NH4]+	193.2	32859911
AllCCS	[M+Na]+	193.9	32859911
AllCCS	[M-H]-	187.9	32859911
AllCCS	[M+Na-2H]-	189.7	32859911
AllCCS	[M+HCOO]-	191.8	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.	7.18 minutes	32390414
Predicted by Siyang on May 30, 2022	24.0719 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.94 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3213.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	425.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	206.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	278.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	639.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1032.3 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	543.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2147.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	712.4 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	1717.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	749.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	493.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	349.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	526.3 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
8(S)-HPETE	CCCCC\C=C/C\C=C/C=C/[C@H](C\C=C/CCCC(O)=O)OO	4118.2	Standard polar	33892256
8(S)-HPETE	CCCCC\C=C/C\C=C/C=C/[C@H](C\C=C/CCCC(O)=O)OO	2442.1	Standard non polar	33892256
8(S)-HPETE	CCCCC\C=C/C\C=C/C=C/[C@H](C\C=C/CCCC(O)=O)OO	2685.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8(S)-HPETE,1TMS,isomer #1	CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)OO	2764.8	Semi standard non polar	33892256
8(S)-HPETE,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C=C\[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)OO	3008.6	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 - 8(S)-HPETE GC-MS (Non-derivatized) - 70eV, Positive	splash10-0lxx-8191000000-f40887afa4336a868504	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8(S)-HPETE GC-MS (1 TMS) - 70eV, Positive	splash10-00bi-9155000000-e96fa4ff2ceea124c320	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8(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 - 8(S)-HPETE 10V, Positive-QTOF	splash10-014i-0129000000-8ca36286a5e0a67d34cd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 20V, Positive-QTOF	splash10-014m-5895000000-74183959cbae04641d81	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 40V, Positive-QTOF	splash10-0296-9730000000-251dda1c693004c0368c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 10V, Negative-QTOF	splash10-000i-0019000000-20280b5caa4db081c46e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 20V, Negative-QTOF	splash10-014r-1659000000-31c2ae506e12aab615b0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 40V, Negative-QTOF	splash10-0a4i-9640000000-dccb96b68f4a42b91f86	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 10V, Positive-QTOF	splash10-0f79-0249000000-d5ea800935198f250188	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 20V, Positive-QTOF	splash10-0gc9-9434000000-0cc74650205c54d85c02	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 40V, Positive-QTOF	splash10-07yl-9410000000-c6a25f739c7950cc8fb4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 10V, Negative-QTOF	splash10-000i-0009000000-f88ebc71b1e75c2910f4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 20V, Negative-QTOF	splash10-0f79-1239000000-4d552d722c2cfa992c86	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8(S)-HPETE 40V, Negative-QTOF	splash10-0a4i-9630000000-578d68ba95d3cb6d39f3	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

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

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023412

KNApSAcK ID

Not Available

Chemspider ID

7827803

KEGG Compound ID

C14823

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9548880

PDB ID

Not Available

ChEBI ID

34487

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jisaka M, Iwanaga C, Takahashi N, Goto T, Kawada T, Yamamoto T, Ikeda I, Nishimura K, Nagaya T, Fushiki T, Yokota K: Double dioxygenation by mouse 8S-lipoxygenase: specific formation of a potent peroxisome proliferator-activated receptor alpha agonist. Biochem Biophys Res Commun. 2005 Dec 9;338(1):136-43. Epub 2005 Aug 15. [PubMed:16112079 ]

Enzymes

Enzyme Details

1. 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 → 8(S)-HPETE	details

Showing metabocard for 8(S)-HPETE (HMDB0004699)

MOL for HMDB0004699 (8(S)-HPETE)

3D MOL for HMDB0004699 (8(S)-HPETE)

3D SDF for HMDB0004699 (8(S)-HPETE)

3D-SDF for HMDB0004699 (8(S)-HPETE)

PDB for HMDB0004699 (8(S)-HPETE)

3D PDB for HMDB0004699 (8(S)-HPETE)

SMILES for HMDB0004699 (8(S)-HPETE)

INCHI for HMDB0004699 (8(S)-HPETE)

Structure for HMDB0004699 (8(S)-HPETE)

3D Structure for HMDB0004699 (8(S)-HPETE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions