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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-10-29 12:41:53 UTC

Update Date

2022-03-07 02:51:03 UTC

HMDB ID

HMDB0011135

Secondary Accession Numbers

HMDB11135

Metabolite Identification

Common Name

5-HPETE

Description

5-HPETE, also known as 5(S)-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, 5-HPETE is considered to be an eicosanoid lipid molecule. 5-HPETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

HMDB0011135
     RDKit          3D
5-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -7.1690    0.5536   -2.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3822    0.7703   -1.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1194    1.1564   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1306    0.0288   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    0.3297   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0409    0.5049    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5598   -0.1943    2.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6682   -1.3342    2.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1891   -1.9405    1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477   -2.0108    0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496   -1.4351    1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524   -2.4319    1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012   -2.3147    1.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9434   -1.2533    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2284   -1.2320    0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568   -0.1503   -0.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538    1.1927   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447    2.3050   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4939    2.5648   -0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4502    1.5727   -1.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1657    0.9671   -0.3068 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6538    1.2244   -2.5000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444   -0.3249   -1.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2960   -0.6995   -2.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1020    0.7801   -3.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3109    1.1397   -3.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9023   -0.5219   -3.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1586    1.5658   -1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7837   -0.1370   -0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3657    1.3268    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7306    2.1061   -1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4788   -0.9207   -0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9535   -0.0862   -1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0829   -0.4080   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280    1.3534   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7252    1.3509    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8826    0.1312    3.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2490   -2.1370    2.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -1.1016    2.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9258   -2.4474    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6913   -2.5092   -0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663   -0.8705    2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6344   -0.6393    0.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -3.2944    2.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0663   -3.1222    1.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543   -0.4580    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8539   -2.0146    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9272   -0.2747   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793    1.2904    1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.3042    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    3.2668   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7773    2.2273   -1.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6412    3.5264   -1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8163    2.9054    0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8677    0.2606   -2.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8320   -1.4411   -2.2287 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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  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
 16 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
 11 43  1  0
 12 44  1  0
 13 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 02241201202D          

 24 23  0  0  1  0            999 V2000
   14.3156   -8.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1406   -8.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5531   -8.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3781   -8.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7906   -9.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6156   -9.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0281  -10.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8531  -10.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2656  -11.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0906  -11.0524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8531  -11.7669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3781  -10.3379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5531  -10.3379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9031   -8.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0781   -8.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6656   -9.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0781  -10.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6656  -11.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0781  -11.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9031  -11.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3156  -12.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1406  -12.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5531  -13.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3781  -13.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  1  6  0  0  0
 13 12  1  0  0  0  0
 14  1  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011135

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO

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

> <INCHI_KEY>
JNUUNUQHXIOFDA-XTDASVJISA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.53405629387521

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid

> <ALOGPS_LOGP>
5.92

> <JCHEM_LOGP>
5.805695121333333

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712375181179874

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.3904738868948

> <JCHEM_PKA_STRONGEST_BASIC>
-4.236807969194996

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
102.81970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011135
     RDKit          3D
5-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -7.1690    0.5536   -2.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3822    0.7703   -1.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1194    1.1564   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1306    0.0288   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    0.3297   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0409    0.5049    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5598   -0.1943    2.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6682   -1.3342    2.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1891   -1.9405    1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477   -2.0108    0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496   -1.4351    1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524   -2.4319    1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012   -2.3147    1.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9434   -1.2533    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2284   -1.2320    0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568   -0.1503   -0.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538    1.1927   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447    2.3050   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4939    2.5648   -0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4502    1.5727   -1.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1657    0.9671   -0.3068 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6538    1.2244   -2.5000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444   -0.3249   -1.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2960   -0.6995   -2.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1020    0.7801   -3.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3109    1.1397   -3.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9023   -0.5219   -3.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1586    1.5658   -1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7837   -0.1370   -0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3657    1.3268    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7306    2.1061   -1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4788   -0.9207   -0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9535   -0.0862   -1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0829   -0.4080   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280    1.3534   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7252    1.3509    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8826    0.1312    3.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2490   -2.1370    2.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -1.1016    2.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9258   -2.4474    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6913   -2.5092   -0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663   -0.8705    2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6344   -0.6393    0.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -3.2944    2.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0663   -3.1222    1.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543   -0.4580    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8539   -2.0146    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9272   -0.2747   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793    1.2904    1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.3042    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    3.2668   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7773    2.2273   -1.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6412    3.5264   -1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8163    2.9054    0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8677    0.2606   -2.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8320   -1.4411   -2.2287 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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  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
 16 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
 11 43  1  0
 12 44  1  0
 13 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      26.722 -15.296   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.262 -15.296   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.032 -16.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.572 -16.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.342 -17.964   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.882 -17.964   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.652 -19.297   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.192 -19.297   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.962 -20.631   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      37.502 -20.631   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      35.192 -21.965   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      30.572 -19.297   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      29.032 -19.297   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      25.952 -16.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.412 -16.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.642 -17.964   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.412 -19.297   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.642 -20.631   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.412 -21.965   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.952 -21.965   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.722 -23.298   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.262 -23.298   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.032 -24.632   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.572 -24.632   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13                                                       
CONECT   13   12                                                            
CONECT   14    1   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0011135
HETATM    1  C1  UNL     1      -7.169   0.554  -2.888  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.382   0.770  -1.414  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.119   1.156  -0.682  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.131   0.029  -0.871  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.801   0.330  -0.160  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.041   0.505   1.269  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.560  -0.194   2.244  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.668  -1.334   2.252  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.189  -1.941   1.049  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.948  -2.011   0.639  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.150  -1.435   1.423  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.152  -2.432   1.836  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.401  -2.315   1.475  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.943  -1.253   0.669  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.228  -1.232   0.365  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.857  -0.150  -0.474  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.454   1.193  -0.017  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.045   2.305  -0.776  1.00  0.00           C  
HETATM   19  C19 UNL     1       6.494   2.565  -0.733  1.00  0.00           C  
HETATM   20  C20 UNL     1       7.450   1.573  -1.176  1.00  0.00           C  
HETATM   21  O1  UNL     1       8.166   0.967  -0.307  1.00  0.00           O  
HETATM   22  O2  UNL     1       7.654   1.224  -2.500  1.00  0.00           O  
HETATM   23  O3  UNL     1       4.344  -0.325  -1.792  1.00  0.00           O  
HETATM   24  O4  UNL     1       5.296  -0.699  -2.609  1.00  0.00           O  
HETATM   25  H1  UNL     1      -8.102   0.780  -3.463  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.311   1.140  -3.282  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.902  -0.522  -3.049  1.00  0.00           H  
HETATM   28  H4  UNL     1      -8.159   1.566  -1.231  1.00  0.00           H  
HETATM   29  H5  UNL     1      -7.784  -0.137  -0.919  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.366   1.327   0.367  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.731   2.106  -1.099  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.479  -0.921  -0.471  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.954  -0.086  -1.959  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.083  -0.408  -0.492  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.528   1.353  -0.634  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.725   1.351   1.565  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.883   0.131   3.283  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.249  -2.137   2.894  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.845  -1.102   2.996  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.926  -2.447   0.387  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.691  -2.509  -0.314  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.166  -0.871   2.317  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.634  -0.639   0.780  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.842  -3.294   2.463  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.066  -3.122   1.844  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.354  -0.458   0.287  1.00  0.00           H  
HETATM   47  H23 UNL     1       4.854  -2.015   0.728  1.00  0.00           H  
HETATM   48  H24 UNL     1       5.927  -0.275  -0.540  1.00  0.00           H  
HETATM   49  H25 UNL     1       4.779   1.290   1.075  1.00  0.00           H  
HETATM   50  H26 UNL     1       3.334   1.304   0.077  1.00  0.00           H  
HETATM   51  H27 UNL     1       4.530   3.267  -0.478  1.00  0.00           H  
HETATM   52  H28 UNL     1       4.777   2.227  -1.883  1.00  0.00           H  
HETATM   53  H29 UNL     1       6.641   3.526  -1.357  1.00  0.00           H  
HETATM   54  H30 UNL     1       6.816   2.905   0.310  1.00  0.00           H  
HETATM   55  H31 UNL     1       7.868   0.261  -2.706  1.00  0.00           H  
HETATM   56  H32 UNL     1       5.832  -1.441  -2.229  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   42   43
CONECT   12   13   13   44
CONECT   13   14   45
CONECT   14   15   15   46
CONECT   15   16   47
CONECT   16   17   23   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

HMDB0011135
     RDKit          3D
5-HPETE
 56 55  0  0  0  0  0  0  0  0999 V2000
   -7.1690    0.5536   -2.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3822    0.7703   -1.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1194    1.1564   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1306    0.0288   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    0.3297   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0409    0.5049    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5598   -0.1943    2.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6682   -1.3342    2.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1891   -1.9405    1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477   -2.0108    0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496   -1.4351    1.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524   -2.4319    1.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012   -2.3147    1.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9434   -1.2533    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2284   -1.2320    0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568   -0.1503   -0.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538    1.1927   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447    2.3050   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4939    2.5648   -0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4502    1.5727   -1.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1657    0.9671   -0.3068 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6538    1.2244   -2.5000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444   -0.3249   -1.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2960   -0.6995   -2.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1020    0.7801   -3.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3109    1.1397   -3.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9023   -0.5219   -3.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1586    1.5658   -1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7837   -0.1370   -0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3657    1.3268    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7306    2.1061   -1.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4788   -0.9207   -0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9535   -0.0862   -1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0829   -0.4080   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280    1.3534   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7252    1.3509    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8826    0.1312    3.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2490   -2.1370    2.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -1.1016    2.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9258   -2.4474    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6913   -2.5092   -0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663   -0.8705    2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6344   -0.6393    0.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -3.2944    2.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0663   -3.1222    1.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543   -0.4580    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8539   -2.0146    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9272   -0.2747   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793    1.2904    1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.3042    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    3.2668   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7773    2.2273   -1.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6412    3.5264   -1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8163    2.9054    0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8677    0.2606   -2.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8320   -1.4411   -2.2287 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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  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
 16 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
 11 43  1  0
 12 44  1  0
 13 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
(6E,8Z,11Z,14Z)-5-Hydroperoxyicosatetraenoic acid	HMDB
5-Hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acid	HMDB
5-Hydroperoxy-(6E,8Z,11Z,14Z)-icosatetraenoic acid	HMDB
6,8,11,14-Eicosatetraenoic acid 5-hydroperoxide	HMDB
Arachidonic acid 5-hydroperoxide	HMDB
(6E,8Z,11Z,14Z)-5-Hydroperoxyicosatetraenoate	HMDB
5-Hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate	HMDB
5-Hydroperoxy-(6E,8Z,11Z,14Z)-icosatetraenoate	HMDB
6,8,11,14-Eicosatetraenoate 5-hydroperoxide	HMDB
Arachidonate 5-hydroperoxide	HMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoate	HMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acid	HMDB
(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoate	HMDB
(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid	HMDB
5(S)-HPETE	HMDB
5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate	HMDB
5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid	HMDB
5-Hydroperoxy-6,8,11,14-eicosatetraenoic acid	HMDB
cis,trans-5-Hydroperoxy-6,8,11,14-eicosatetraenoic acid	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid

Traditional Name

(6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid

CAS Registry Number

74581-83-2

SMILES

CCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO

InChI Identifier

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

InChI Key

JNUUNUQHXIOFDA-XTDASVJISA-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0011135)
Membrane (HMDB: HMDB0011135)

Source

Exogenous

Exogenous (HMDB: HMDB0011135)

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: HMDB0011135)

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	0.0016 g/L	ALOGPS
logP	5.92	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]+	193.453	31661259
DarkChem	[M-H]-	192.227	31661259
DeepCCS	[M+H]+	189.134	30932474
DeepCCS	[M-H]-	186.776	30932474
DeepCCS	[M-2H]-	219.662	30932474
DeepCCS	[M+Na]+	195.227	30932474
AllCCS	[M+H]+	190.6	32859911
AllCCS	[M+H-H2O]+	187.7	32859911
AllCCS	[M+NH4]+	193.2	32859911
AllCCS	[M+Na]+	193.9	32859911
AllCCS	[M-H]-	188.1	32859911
AllCCS	[M+Na-2H]-	190.0	32859911
AllCCS	[M+HCOO]-	192.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.14 minutes	32390414
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.	7.28 minutes	32390414
Predicted by Siyang on May 30, 2022	24.9494 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.77 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3247.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	480.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	213.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	310.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	665.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1089.9 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	570.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2199.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	730.0 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	1826.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	798.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	508.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	363.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	532.4 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-HPETE	CCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO	4170.8	Standard polar	33892256
5-HPETE	CCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO	2397.0	Standard non polar	33892256
5-HPETE	CCCCC\C=C/C\C=C/C\C=C/C=C/C(CCCC(O)=O)OO	2644.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-HPETE,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O[Si](C)(C)C)OO	2757.3	Semi standard non polar	33892256
5-HPETE,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O[Si](C)(C)C(C)(C)C)OO	2999.1	Semi standard non polar	33892256

Spectra

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

FDB027913

KNApSAcK ID

Not Available

Chemspider ID

4446295

KEGG Compound ID

C05356

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Arachidonic acid 5-hydroperoxide

METLIN ID

Not Available

PubChem Compound

5283171

PDB ID

Not Available

ChEBI ID

91268

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

Winkler JD, Sung CM, Hubbard WC, Chilton FH: Influence of arachidonic acid on indices of phospholipase A2 activity in the human neutrophil. Biochem J. 1993 May 1;291 ( Pt 3):825-31. [PubMed:8387780 ]
Seya A, Terano T, Tamura Y, Yoshida S: The role of 5-hydroperoxyeicosatetraenoic acid in neutrophil activation. Agents Actions. 1992 Sep;37(1-2):121-6. [PubMed:1456173 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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

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

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

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

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

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

Enzyme Details

8. Arachidonate 5-lipoxygenase

General function:: Involved in metal ion binding
Specific function:: Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:: ALOX5
Uniprot ID:: P09917
Molecular weight:: 77982.595

Showing metabocard for 5-HPETE (HMDB0011135)

MOL for HMDB0011135 (5-HPETE)

3D MOL for HMDB0011135 (5-HPETE)

3D SDF for HMDB0011135 (5-HPETE)

3D-SDF for HMDB0011135 (5-HPETE)

PDB for HMDB0011135 (5-HPETE)

3D PDB for HMDB0011135 (5-HPETE)

SMILES for HMDB0011135 (5-HPETE)

INCHI for HMDB0011135 (5-HPETE)

Structure for HMDB0011135 (5-HPETE)

3D Structure for HMDB0011135 (5-HPETE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes