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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 15:05:29 UTC

Update Date

2022-03-07 02:49:20 UTC

HMDB ID

HMDB0004243

Secondary Accession Numbers

HMDB04243

Metabolite Identification

Common Name

12(S)-HPETE

Description

12-HPETE is one of the six monohydroperoxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid (Leukotrienes). Reduction of the hydroperoxide yields the more stable hydroxyl fatty acid (+/-)12-HETE. A family of biologically active compounds derived from arachidonic acid by oxidative metabolism through the 5-lipoxygenase pathway. They participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. They have potent actions on many essential organs and systems, including the cardiovascular, pulmonary, and central nervous system as well as the gastrointestinal tract and the immune system.

Structure

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

HMDB0004243
     RDKit          3D
12(S)-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -9.3115   -0.4478   -0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6229   -0.1400    0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2143   -0.6934    0.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4584   -0.0507   -0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0228   -0.5591   -0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -0.2602    0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236    0.4926    0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5917    1.1293   -0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708    0.6118   -0.6566 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3656    0.9128    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9862    0.8680    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7513    1.1641    1.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0548    1.1244    1.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062    0.7866    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7011   -0.3826    0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0005   -0.3636    0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625    0.8130    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6356    0.7078   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6328   -0.3752   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0993   -1.7406   -0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9191   -1.9261   -1.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8987   -2.8695   -0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1803   -0.7566   -0.8539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6545   -1.1273   -1.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4310    0.4711   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7564   -1.2407   -1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3154   -0.8449   -0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5331    0.9723    0.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1703   -0.5883    1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1757   -1.7829    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7443   -0.2971    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8898   -0.2627   -1.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4218    1.0452   -0.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5716   -0.1566   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0725   -1.6942   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6823   -0.6887    1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7370    0.6744    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    1.0030   -1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5324    2.2603   -0.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139    1.1369   -1.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.1807    1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638    0.6021   -0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447    1.4240    2.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6415    1.3544    2.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    0.4227   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800    1.6460    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627   -1.3052    1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5903   -1.2594    1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2357    1.7814    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5179    0.9762    1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9355    0.5391   -1.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0775    1.7152   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2388   -0.1824   -1.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4125   -0.3245    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6988   -3.4560    0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -2.0393   -1.9958 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  1  0
 10 11  2  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
  9 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  6
 10 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

Untitled Document-4
  Mrv0541 02231219542D          

 24 23  0  0  0  0            999 V2000
   -4.2087    4.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4035    4.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565    3.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3513    3.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    2.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    2.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0522    1.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104    1.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3634    0.2695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5582    0.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3112   -0.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940   -0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409   -1.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -2.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297   -3.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2349   -3.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931   -2.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -2.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453   -3.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6505   -3.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -4.5647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087   -3.1701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9216   -0.3379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798   -0.9454    0.0000 O   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
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 20 22  2  0  0  0  0
 16 17  1  0  0  0  0
 14 13  1  0  0  0  0
  7  8  1  0  0  0  0
  9 23  1  1  0  0  0
 23 24  1  0  0  0  0
M  STY  1   1 SUP
M  SAL   1  2  23  24
M  SBL   1  1  22
M  SMT   1 ^OOH
M  END
> <DATABASE_ID>
HMDB0004243

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1

> <INCHI_KEY>
ZIOZYRSDNLNNNJ-LQWMCKPYSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.1229301291

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z,10E,12S,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid

> <ALOGPS_LOGP>
5.90

> <JCHEM_LOGP>
5.805695121333333

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.711074265715716

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.889630441718793

> <JCHEM_PKA_STRONGEST_BASIC>
-4.237376144832212

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
102.8197

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-HpETE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004243
     RDKit          3D
12(S)-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -9.3115   -0.4478   -0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6229   -0.1400    0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2143   -0.6934    0.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4584   -0.0507   -0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0228   -0.5591   -0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -0.2602    0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236    0.4926    0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5917    1.1293   -0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708    0.6118   -0.6566 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3656    0.9128    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9862    0.8680    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7513    1.1641    1.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0548    1.1244    1.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062    0.7866    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7011   -0.3826    0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0005   -0.3636    0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625    0.8130    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6356    0.7078   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6328   -0.3752   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0993   -1.7406   -0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9191   -1.9261   -1.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8987   -2.8695   -0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1803   -0.7566   -0.8539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6545   -1.1273   -1.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4310    0.4711   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7564   -1.2407   -1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3154   -0.8449   -0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5331    0.9723    0.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1703   -0.5883    1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1757   -1.7829    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7443   -0.2971    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8898   -0.2627   -1.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4218    1.0452   -0.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5716   -0.1566   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0725   -1.6942   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6823   -0.6887    1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7370    0.6744    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    1.0030   -1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5324    2.2603   -0.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139    1.1369   -1.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.1807    1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638    0.6021   -0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447    1.4240    2.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6415    1.3544    2.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    0.4227   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800    1.6460    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627   -1.3052    1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5903   -1.2594    1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2357    1.7814    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5179    0.9762    1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9355    0.5391   -1.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0775    1.7152   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2388   -0.1824   -1.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4125   -0.3245    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6988   -3.4560    0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -2.0393   -1.9958 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  1  0
 10 11  2  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
  9 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  6
 10 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    MOLECULE: Untitled Document-4                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.856   8.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.353   8.186   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.892   6.716   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.389   6.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.928   4.911   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.425   4.576   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.964   3.107   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.006   1.973   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.545   0.503   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.042   0.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.581  -1.302   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.922  -1.637   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.383  -3.107   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.341  -4.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.802  -5.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.305  -6.045   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.347  -4.911   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.850  -5.247   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.311  -6.716   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.814  -7.052   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.275  -8.521   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.856  -5.918   0.000  0.00  0.00           O+0
HETATM   23  O   ^OOH     1      -3.587  -0.631   0.000  0.00  0.00           O+0
HETATM   24  O   ^OOH     1      -4.629  -1.765   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    9    7                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   15   13                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   18   16                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   24    9                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0004243
HETATM    1  C1  UNL     1      -9.311  -0.448  -0.773  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.623  -0.140   0.534  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.214  -0.693   0.547  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.458  -0.051  -0.594  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.023  -0.559  -0.644  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.302  -0.260   0.609  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.224   0.493   0.637  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.592   1.129  -0.515  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.171   0.612  -0.657  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.366   0.913   0.552  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.986   0.868   0.513  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.751   1.164   1.703  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.055   1.124   1.694  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.906   0.787   0.522  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.701  -0.383   0.869  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.000  -0.364   0.903  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.763   0.813   0.604  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.636   0.708  -0.600  1.00  0.00           C  
HETATM   19  C19 UNL     1       8.633  -0.375  -0.674  1.00  0.00           C  
HETATM   20  C20 UNL     1       8.099  -1.741  -0.819  1.00  0.00           C  
HETATM   21  O1  UNL     1       6.919  -1.926  -1.175  1.00  0.00           O  
HETATM   22  O2  UNL     1       8.899  -2.869  -0.566  1.00  0.00           O  
HETATM   23  O3  UNL     1      -1.180  -0.757  -0.854  1.00  0.00           O  
HETATM   24  O4  UNL     1      -0.655  -1.127  -1.995  1.00  0.00           O  
HETATM   25  H1  UNL     1      -9.431   0.471  -1.399  1.00  0.00           H  
HETATM   26  H2  UNL     1      -8.756  -1.241  -1.331  1.00  0.00           H  
HETATM   27  H3  UNL     1     -10.315  -0.845  -0.533  1.00  0.00           H  
HETATM   28  H4  UNL     1      -8.533   0.972   0.687  1.00  0.00           H  
HETATM   29  H5  UNL     1      -9.170  -0.588   1.388  1.00  0.00           H  
HETATM   30  H6  UNL     1      -7.176  -1.783   0.496  1.00  0.00           H  
HETATM   31  H7  UNL     1      -6.744  -0.297   1.492  1.00  0.00           H  
HETATM   32  H8  UNL     1      -6.890  -0.263  -1.585  1.00  0.00           H  
HETATM   33  H9  UNL     1      -6.422   1.045  -0.436  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.572  -0.157  -1.542  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.073  -1.694  -0.699  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.682  -0.689   1.570  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.737   0.674   1.611  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.069   1.003  -1.489  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.532   2.260  -0.385  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.714   1.137  -1.512  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.786   1.181   1.510  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.364   0.602  -0.458  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.245   1.424   2.619  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.642   1.354   2.614  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.191   0.423  -0.283  1.00  0.00           H  
HETATM   46  H22 UNL     1       4.380   1.646   0.078  1.00  0.00           H  
HETATM   47  H23 UNL     1       4.163  -1.305   1.108  1.00  0.00           H  
HETATM   48  H24 UNL     1       6.590  -1.259   1.220  1.00  0.00           H  
HETATM   49  H25 UNL     1       6.236   1.781   0.515  1.00  0.00           H  
HETATM   50  H26 UNL     1       7.518   0.976   1.478  1.00  0.00           H  
HETATM   51  H27 UNL     1       6.936   0.539  -1.492  1.00  0.00           H  
HETATM   52  H28 UNL     1       8.077   1.715  -0.860  1.00  0.00           H  
HETATM   53  H29 UNL     1       9.239  -0.182  -1.617  1.00  0.00           H  
HETATM   54  H30 UNL     1       9.412  -0.325   0.128  1.00  0.00           H  
HETATM   55  H31 UNL     1       8.699  -3.456   0.256  1.00  0.00           H  
HETATM   56  H32 UNL     1      -0.318  -2.039  -1.996  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   23   40
CONECT   10   11   11   41
CONECT   11   12   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

HMDB0004243
     RDKit          3D
12(S)-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -9.3115   -0.4478   -0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6229   -0.1400    0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2143   -0.6934    0.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4584   -0.0507   -0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0228   -0.5591   -0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -0.2602    0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236    0.4926    0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5917    1.1293   -0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708    0.6118   -0.6566 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3656    0.9128    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9862    0.8680    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7513    1.1641    1.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0548    1.1244    1.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062    0.7866    0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7011   -0.3826    0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0005   -0.3636    0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625    0.8130    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6356    0.7078   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6328   -0.3752   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0993   -1.7406   -0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9191   -1.9261   -1.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8987   -2.8695   -0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1803   -0.7566   -0.8539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6545   -1.1273   -1.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4310    0.4711   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7564   -1.2407   -1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3154   -0.8449   -0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5331    0.9723    0.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1703   -0.5883    1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1757   -1.7829    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7443   -0.2971    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8898   -0.2627   -1.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4218    1.0452   -0.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5716   -0.1566   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0725   -1.6942   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6823   -0.6887    1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7370    0.6744    1.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    1.0030   -1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5324    2.2603   -0.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139    1.1369   -1.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.1807    1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638    0.6021   -0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447    1.4240    2.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6415    1.3544    2.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    0.4227   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800    1.6460    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627   -1.3052    1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5903   -1.2594    1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2357    1.7814    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5179    0.9762    1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9355    0.5391   -1.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0775    1.7152   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2388   -0.1824   -1.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4125   -0.3245    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6988   -3.4560    0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -2.0393   -1.9958 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  1  0
 10 11  2  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
  9 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  6
 10 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,10E,14Z)-(12S)-12-Hydroperoxyeicosa-5,8,10,14-tetraenoate	ChEBI
(5Z,8Z,10E,14Z)-(12S)-12-Hydroperoxyicosa-5,8,10,14-tetraenoate	ChEBI
(5Z,8Z,10E,14Z)-(12S)-12-Hydroperoxyicosa-5,8,10,14-tetraenoic acid	ChEBI
12-HpETE	ChEBI
12-Hydroperoxyeicosatetraenoate	ChEBI
12-Hydroperoxyeicosatetraenoic acid	ChEBI
12-Hydroperoxyicosatetraenoate	ChEBI
12-Hydroperoxyicosatetraenoic acid	ChEBI
12-Oohete	ChEBI
Arachidonic acid omega-9 hydroperoxide	ChEBI
Omega-9 hpaa	ChEBI
Omega-9-hydroperoxyarachidonic acid	ChEBI
(5Z,8Z,10E,14Z)-(12S)-12-Hydroperoxyeicosa-5,8,10,14-tetraenoic acid	Generator
Arachidonate omega-9 hydroperoxide	Generator
Omega-9-hydroperoxyarachidonate	Generator
(5Z,8Z,10E,12S,14Z)-12-Hydroperoxyicosa-5,8,10,14-tetraenoic acid	HMDB
(5Z,8Z,10E,12S,14Z)-12-Hydroperoxyicosa-5,8,10,14-tetraenoate	HMDB
12-HPETE, (S-(e,e,e))-isomer	HMDB
12-L-Hydroperoxy-5,8,10,14-eicosatetraenoic acid	HMDB
12-Hydroperoxy-5,8,10,14-icosatetraenoic acid	HMDB
12-HPETE, (e,Z,Z,Z)-isomer	HMDB
12-HPETE, (S-(e,Z,Z,Z))-isomer	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(5Z,8Z,10E,12S,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid

Traditional Name

12-HpETE

CAS Registry Number

71774-10-2

SMILES

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

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1

InChI Key

ZIOZYRSDNLNNNJ-LQWMCKPYSA-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:15626 )
Hydroperoxy fatty acids (C05965 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060013 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cell

Hematocyte

Platelet (HMDB: HMDB0004243)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0004243)

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: HMDB0004243)

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

Liquid

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	5.9	ALOGPS
logP	5.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.89	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	39.12 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]+	193.082	31661259
DarkChem	[M-H]-	190.794	31661259
DeepCCS	[M+H]+	192.206	30932474
DeepCCS	[M-H]-	189.848	30932474
DeepCCS	[M-2H]-	222.734	30932474
DeepCCS	[M+Na]+	198.299	30932474
AllCCS	[M+H]+	190.5	32859911
AllCCS	[M+H-H2O]+	187.7	32859911
AllCCS	[M+NH4]+	193.1	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.	7.11 minutes	32390414
Predicted by Siyang on May 30, 2022	24.071 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.09 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	3213.5 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	278.7 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	1032.4 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	543.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2147.7 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	1717.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	749.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	493.1 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
12(S)-HPETE	CCCCC\C=C/C[C@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O	4123.6	Standard polar	33892256
12(S)-HPETE	CCCCC\C=C/C[C@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O	2442.4	Standard non polar	33892256
12(S)-HPETE	CCCCC\C=C/C[C@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O	2685.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12(S)-HPETE,1TMS,isomer #1	CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)OO	2764.4	Semi standard non polar	33892256
12(S)-HPETE,1TBDMS,isomer #1	CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)OO	3008.1	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 - 12(S)-HPETE GC-MS (Non-derivatized) - 70eV, Positive	splash10-0nml-8491000000-0127633b6ae0909f1672	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12(S)-HPETE GC-MS (1 TMS) - 70eV, Positive	splash10-05dr-9334000000-7ccf269dc3d82ad47d27	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12(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 - 12(S)-HPETE 10V, Positive-QTOF	splash10-014i-0119000000-663dc7dd460df95c9d6d	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 20V, Positive-QTOF	splash10-00pl-5975000000-e3fe517c22245902e6d2	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 40V, Positive-QTOF	splash10-052f-9640000000-1c2eba4af6221c6ee488	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 10V, Negative-QTOF	splash10-000i-0129000000-9b31acab4f79d4ab744c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 20V, Negative-QTOF	splash10-014r-1659000000-5db483e2b6ae8fccb37e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 40V, Negative-QTOF	splash10-0a4i-9740000000-a88fa00904c08bd3dbfe	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 10V, Positive-QTOF	splash10-0f79-0249000000-702a285b6044fb920d29	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 20V, Positive-QTOF	splash10-0f79-7977000000-3cd8fc7d5c58fa9ef000	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 40V, Positive-QTOF	splash10-066u-9420000000-b47740fabc6ca56ad6c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 10V, Negative-QTOF	splash10-000i-0009000000-7847d679fdeeabe38573	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 20V, Negative-QTOF	splash10-0udr-0329000000-d4296bbebfcef533338a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-HPETE 40V, Negative-QTOF	splash10-056u-3690000000-c9e5a737326ebfdd3bf0	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Platelet

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	0.00145 +/- 0.0023 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

FDB023348

KNApSAcK ID

Not Available

Chemspider ID

4444415

KEGG Compound ID

C05965

BioCyc ID

Not Available

BiGG ID

44618

Wikipedia Link

Not Available

METLIN ID

7038

PubChem Compound

5280892

PDB ID

Not Available

ChEBI ID

15626

Food Biomarker Ontology

Not Available

VMH ID

12HPET

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Nagata, Ryu; Kawakami, Masayuki; Matsuura, Teruo; Saito, Isao. Synthesis of 12-hydroperoxyeicosatetraenoic acid (12-HPETE). On the stereochemistry in the conversion of 12(S)-HETE to 12-HPETE. Tetrahedron Letters (1989), 30(21), 2817-20.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Boutaud O, Aronoff DM, Richardson JH, Marnett LJ, Oates JA: Determinants of the cellular specificity of acetaminophen as an inhibitor of prostaglandin H(2) synthases. Proc Natl Acad Sci U S A. 2002 May 14;99(10):7130-5. [PubMed:12011469 ]

Enzymes

Enzyme Details

1. Arachidonate 12-lipoxygenase, 12S-type

General function:: Involved in metal ion binding
Specific function:: Oxygenase and 14,15-leukotriene A4 synthase activity.
Gene Name:: ALOX12
Uniprot ID:: P18054
Molecular weight:: 75693.38

Reactions

Arachidonic acid + Oxygen → 12(S)-HPETE	details

Showing metabocard for 12(S)-HPETE (HMDB0004243)

MOL for HMDB0004243 (12(S)-HPETE)

3D MOL for HMDB0004243 (12(S)-HPETE)

3D SDF for HMDB0004243 (12(S)-HPETE)

3D-SDF for HMDB0004243 (12(S)-HPETE)

PDB for HMDB0004243 (12(S)-HPETE)

3D PDB for HMDB0004243 (12(S)-HPETE)

SMILES for HMDB0004243 (12(S)-HPETE)

INCHI for HMDB0004243 (12(S)-HPETE)

Structure for HMDB0004243 (12(S)-HPETE)

3D Structure for HMDB0004243 (12(S)-HPETE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions