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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 04:41:37 UTC

Update Date

2022-03-07 03:17:57 UTC

HMDB ID

HMDB0062616

Secondary Accession Numbers

HMDB62616

Metabolite Identification

Common Name

(5S)-hydroperoxy-18-hydroxy-EPE

Description

(5S,6E,8Z,11Z,14Z)-5-hydroperoxy-18-hydroxyicosa-6,8,11,14,16-pentaenoic acid belongs to the class of organic compounds known as hydroperoxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and five CC double bonds (5S,6E,8Z,11Z,14Z)-5-hydroperoxy-18-hydroxyicosa-6,8,11,14,16-pentaenoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv1652303231705412D          

 37 36  0  0  1  0            999 V2000
    0.8250   -7.1447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -5.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -6.4302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -6.4302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -7.8592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -7.8592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -8.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -7.1447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -6.4302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -5.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8875   -3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  4  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 28 36  1  1  0  0  0
 36 37  1  0  0  0  0
M  END

HMDB0062616
     RDKit          3D
(5S)-hydroperoxy-18-hydroxy-EPE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -8.1171   -1.4575   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3324   -1.0740    0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6805    0.2707    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9687    0.5892    1.9710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7095    0.1803   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    1.0663   -0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053    0.9507   -1.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202    1.8094   -1.7652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5284    2.9467   -0.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456    3.2117   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752    2.5191   -0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    1.1734   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    0.2657    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799   -0.3850    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3346   -0.3102   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660   -0.9991   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -0.9001   -1.1468 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8842   -1.3243   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1565   -0.3911    0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4338   -0.6561    1.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4689   -1.9843    1.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5091   -2.7661    1.8763 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6175   -2.4260    2.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6831    0.4247   -1.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5220    0.6307   -2.7968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5722   -2.2410   -0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1964   -0.5824   -0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1283   -1.7622    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0301   -0.9769    1.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6139   -1.8724    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4371    1.0332    0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4090    1.4077    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7984   -0.6436   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7037    1.8484    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9277    0.1008   -2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108    1.6054   -2.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558    3.8793   -1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441    3.1733   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3105    4.2259    0.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5602    2.9382    0.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0124    0.7243   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    1.1286   -1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6215    0.2120    1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264   -1.0277    1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2777    0.2894   -1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5598   -1.6114    0.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3346   -1.5178   -2.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958   -2.3732   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6501   -1.1656   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1461    0.6826    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034   -0.4457    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5605    0.1118    2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3067   -0.4960    0.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5358   -2.7923    3.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684    1.5819   -2.8956 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  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  1  0
 21 22  2  0
 21 23  1  0
 17 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 23 54  1  0
 25 55  1  0
M  END


  Mrv1652303231705412D          

 37 36  0  0  1  0            999 V2000
    0.8250   -7.1447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -5.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -6.4302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -6.4302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -7.8592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -7.8592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -8.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -7.1447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -6.4302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -5.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8875   -3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  4  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 28 36  1  1  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062616

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-2-18(21)14-11-9-7-5-3-4-6-8-10-12-15-19(25-24)16-13-17-20(22)23/h3-4,7-12,14-15,18-19,21,24H,2,5-6,13,16-17H2,1H3,(H,22,23)/b4-3-,9-7-,10-8-,14-11?,15-12+/t18?,19-/m1/s1

> <INCHI_KEY>
JIOJPWROWDJRKM-FIYNLQNCSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.455

> <EXACT_MASS>
350.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.29656287470421

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6E,8Z,11Z,14Z)-5-hydroperoxy-18-hydroxyicosa-6,8,11,14,16-pentaenoic acid

> <ALOGPS_LOGP>
4.59

> <JCHEM_LOGP>
4.212962397666665

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712375181179894

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.390474274847268

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6583730850462208

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
105.45179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6E,8Z,11Z,14Z)-5-hydroperoxy-18-hydroxyicosa-6,8,11,14,16-pentaenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062616
     RDKit          3D
(5S)-hydroperoxy-18-hydroxy-EPE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -8.1171   -1.4575   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3324   -1.0740    0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6805    0.2707    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9687    0.5892    1.9710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7095    0.1803   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    1.0663   -0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053    0.9507   -1.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202    1.8094   -1.7652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5284    2.9467   -0.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456    3.2117   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752    2.5191   -0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    1.1734   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    0.2657    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799   -0.3850    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3346   -0.3102   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660   -0.9991   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -0.9001   -1.1468 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8842   -1.3243   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1565   -0.3911    0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4338   -0.6561    1.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4689   -1.9843    1.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5091   -2.7661    1.8763 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6175   -2.4260    2.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6831    0.4247   -1.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5220    0.6307   -2.7968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5722   -2.2410   -0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1964   -0.5824   -0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1283   -1.7622    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0301   -0.9769    1.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6139   -1.8724    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4371    1.0332    0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4090    1.4077    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7984   -0.6436   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7037    1.8484    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9277    0.1008   -2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108    1.6054   -2.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558    3.8793   -1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441    3.1733   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3105    4.2259    0.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5602    2.9382    0.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0124    0.7243   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    1.1286   -1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6215    0.2120    1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264   -1.0277    1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2777    0.2894   -1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5598   -1.6114    0.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3346   -1.5178   -2.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958   -2.3732   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6501   -1.1656   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1461    0.6826    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034   -0.4457    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5605    0.1118    2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3067   -0.4960    0.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5358   -2.7923    3.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684    1.5819   -2.8956 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  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  1  0
 21 22  2  0
 21 23  1  0
 17 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 23 54  1  0
 25 55  1  0
M  END

HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  H   UNK     0       1.540 -13.337   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       2.310 -12.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540 -10.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -10.669   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0      -0.770  -9.336   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0      -0.770 -12.003   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0      -2.310 -12.003   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0       0.000 -13.337   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       0.770 -12.003   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0      -0.770 -14.670   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0      -2.310 -14.670   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       0.000 -16.004   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       0.770 -14.670   0.000  0.00  0.00           H+0
HETATM   14  O   UNK     0       1.540 -16.004   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.770 -17.338   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000 -18.672   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.850 -12.003   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       4.620 -13.337   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       4.620 -10.669   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.160 -10.669   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       6.930 -12.003   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       6.930  -9.336   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       8.470  -9.336   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       6.160  -8.002   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       4.620  -8.002   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       6.930  -6.668   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       8.470  -6.668   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       6.160  -5.335   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       5.390  -6.668   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0       4.620  -5.335   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.310  -4.001   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       6.930  -4.001   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       8.470  -4.001   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16                                                       
CONECT   16   15                                                            
CONECT   17    2   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   36                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   28   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   72    0
END

COMPND    HMDB0062616
HETATM    1  C1  UNL     1      -8.117  -1.457  -0.250  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.332  -1.074   0.999  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.681   0.271   0.800  1.00  0.00           C  
HETATM    4  O1  UNL     1      -5.969   0.589   1.971  1.00  0.00           O  
HETATM    5  C4  UNL     1      -5.709   0.180  -0.311  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.742   1.066  -0.464  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.805   0.951  -1.563  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.820   1.809  -1.765  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.528   2.947  -0.968  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.346   3.212  -0.224  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.275   2.519  -0.025  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.089   1.173  -0.605  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.173   0.266   0.594  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.280  -0.385   0.706  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.335  -0.310  -0.265  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.466  -0.999  -0.115  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.550  -0.900  -1.147  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.884  -1.324  -0.534  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.156  -0.391   0.612  1.00  0.00           C  
HETATM   20  C19 UNL     1       7.434  -0.656   1.330  1.00  0.00           C  
HETATM   21  C20 UNL     1       7.469  -1.984   1.932  1.00  0.00           C  
HETATM   22  O2  UNL     1       6.509  -2.766   1.876  1.00  0.00           O  
HETATM   23  O3  UNL     1       8.617  -2.426   2.607  1.00  0.00           O  
HETATM   24  O4  UNL     1       4.683   0.425  -1.511  1.00  0.00           O  
HETATM   25  O5  UNL     1       4.522   0.631  -2.797  1.00  0.00           O  
HETATM   26  H1  UNL     1      -7.572  -2.241  -0.815  1.00  0.00           H  
HETATM   27  H2  UNL     1      -8.196  -0.582  -0.924  1.00  0.00           H  
HETATM   28  H3  UNL     1      -9.128  -1.762   0.052  1.00  0.00           H  
HETATM   29  H4  UNL     1      -8.030  -0.977   1.855  1.00  0.00           H  
HETATM   30  H5  UNL     1      -6.614  -1.872   1.192  1.00  0.00           H  
HETATM   31  H6  UNL     1      -7.437   1.033   0.551  1.00  0.00           H  
HETATM   32  H7  UNL     1      -6.409   1.408   2.364  1.00  0.00           H  
HETATM   33  H8  UNL     1      -5.798  -0.644  -1.022  1.00  0.00           H  
HETATM   34  H9  UNL     1      -4.704   1.848   0.266  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.928   0.101  -2.260  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.211   1.605  -2.669  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.656   3.879  -1.689  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.444   3.173  -0.304  1.00  0.00           H  
HETATM   39  H14 UNL     1      -1.311   4.226   0.311  1.00  0.00           H  
HETATM   40  H15 UNL     1       0.560   2.938   0.612  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.012   0.724  -1.006  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.682   1.129  -1.360  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.622   0.212   1.325  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.426  -1.028   1.585  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.278   0.289  -1.142  1.00  0.00           H  
HETATM   46  H21 UNL     1       3.560  -1.611   0.757  1.00  0.00           H  
HETATM   47  H22 UNL     1       4.335  -1.518  -2.037  1.00  0.00           H  
HETATM   48  H23 UNL     1       5.796  -2.373  -0.250  1.00  0.00           H  
HETATM   49  H24 UNL     1       6.650  -1.166  -1.325  1.00  0.00           H  
HETATM   50  H25 UNL     1       6.146   0.683   0.280  1.00  0.00           H  
HETATM   51  H26 UNL     1       5.303  -0.446   1.351  1.00  0.00           H  
HETATM   52  H27 UNL     1       7.561   0.112   2.129  1.00  0.00           H  
HETATM   53  H28 UNL     1       8.307  -0.496   0.652  1.00  0.00           H  
HETATM   54  H29 UNL     1       8.536  -2.792   3.533  1.00  0.00           H  
HETATM   55  H30 UNL     1       4.268   1.582  -2.896  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    5   31
CONECT    4   32
CONECT    5    6    6   33
CONECT    6    7   34
CONECT    7    8    8   35
CONECT    8    9   36
CONECT    9   10   37   38
CONECT   10   11   11   39
CONECT   11   12   40
CONECT   12   13   41   42
CONECT   13   14   14   43
CONECT   14   15   44
CONECT   15   16   16   45
CONECT   16   17   46
CONECT   17   18   24   47
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   22   23
CONECT   23   54
CONECT   24   25
CONECT   25   55
END

HMDB0062616
     RDKit          3D
(5S)-hydroperoxy-18-hydroxy-EPE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -8.1171   -1.4575   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3324   -1.0740    0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6805    0.2707    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9687    0.5892    1.9710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7095    0.1803   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    1.0663   -0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053    0.9507   -1.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202    1.8094   -1.7652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5284    2.9467   -0.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456    3.2117   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752    2.5191   -0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    1.1734   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    0.2657    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799   -0.3850    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3346   -0.3102   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660   -0.9991   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -0.9001   -1.1468 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8842   -1.3243   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1565   -0.3911    0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4338   -0.6561    1.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4689   -1.9843    1.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5091   -2.7661    1.8763 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6175   -2.4260    2.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6831    0.4247   -1.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5220    0.6307   -2.7968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5722   -2.2410   -0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1964   -0.5824   -0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1283   -1.7622    0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0301   -0.9769    1.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6139   -1.8724    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4371    1.0332    0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4090    1.4077    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7984   -0.6436   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7037    1.8484    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9277    0.1008   -2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108    1.6054   -2.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558    3.8793   -1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441    3.1733   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3105    4.2259    0.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5602    2.9382    0.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0124    0.7243   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    1.1286   -1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6215    0.2120    1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264   -1.0277    1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2777    0.2894   -1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5598   -1.6114    0.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3346   -1.5178   -2.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958   -2.3732   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6501   -1.1656   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1461    0.6826    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034   -0.4457    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5605    0.1118    2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3067   -0.4960    0.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5358   -2.7923    3.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684    1.5819   -2.8956 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  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  1  0
 21 22  2  0
 21 23  1  0
 17 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 23 54  1  0
 25 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxy-18-hydroxyicosa-6,8,11,14,16-pentaenoate	Generator
(5S)-Hydroperoxy-18-hepe	HMDB
(5S)-Hydroperoxy-18-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoate	HMDB
(5S)-Hydroperoxy-18-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoic acid	HMDB
(5S)-Hydroperoxy-18-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoate	HMDB
(5S)-Hydroperoxy-18-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid	HMDB
(5S,6E,8Z,11Z,14Z,16E)-5-Hydroperoxy-18-hydroxyicosapentaenoate	HMDB
(5S,6E,8Z,11Z,14Z,16E)-5-Hydroperoxy-18-hydroxyicosapentaenoic acid	HMDB
5(S)-HP-18-HEPE	HMDB

Chemical Formula

C₂₀H₃₀O₅

Average Molecular Weight

350.455

Monoisotopic Molecular Weight

350.209324066

IUPAC Name

(5S,6E,8Z,11Z,14Z)-5-hydroperoxy-18-hydroxyicosa-6,8,11,14,16-pentaenoic acid

Traditional Name

(5S,6E,8Z,11Z,14Z)-5-hydroperoxy-18-hydroxyicosa-6,8,11,14,16-pentaenoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O5/c1-2-18(21)14-11-9-7-5-3-4-6-8-10-12-15-19(25-24)16-13-17-20(22)23/h3-4,7-12,14-15,18-19,21,24H,2,5-6,13,16-17H2,1H3,(H,22,23)/b4-3-,9-7-,10-8-,14-11?,15-12+/t18?,19-/m1/s1

InChI Key

JIOJPWROWDJRKM-FIYNLQNCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroperoxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and five CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroperoxyeicosapentaenoic acids

Alternative Parents

Substituents

Hydroperoxyeicosapentaenoic acid
Long-chain fatty acid
Hydroperoxy fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acid
Allylic hydroperoxide
Secondary alcohol
Hydroperoxide
Peroxol
Monocarboxylic acid or derivatives
Alkyl hydroperoxide
Carboxylic acid
Carboxylic acid derivative
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.016 g/l	ALOGPS
LogP	4.59	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.59	ALOGPS
logP	4.21	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	105.45 m³·mol⁻¹	ChemAxon
Polarizability	39.3 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	191.909	31661259
DarkChem	[M-H]-	190.406	31661259
DeepCCS	[M+H]+	202.12	30932474
DeepCCS	[M-H]-	200.225	30932474
DeepCCS	[M-2H]-	234.038	30932474
DeepCCS	[M+Na]+	207.972	30932474
AllCCS	[M+H]+	193.0	32859911
AllCCS	[M+H-H2O]+	190.2	32859911
AllCCS	[M+NH4]+	195.6	32859911
AllCCS	[M+Na]+	196.3	32859911
AllCCS	[M-H]-	188.6	32859911
AllCCS	[M+Na-2H]-	190.4	32859911
AllCCS	[M+HCOO]-	192.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(5S)-hydroperoxy-18-hydroxy-EPE	[H]\C(C\C([H])=C(\[H])C([H])=C([H])C([H])(O)CC)=C(/[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@]([H])(CCCC(O)=O)OO	4645.3	Standard polar	33892256
(5S)-hydroperoxy-18-hydroxy-EPE	[H]\C(C\C([H])=C(\[H])C([H])=C([H])C([H])(O)CC)=C(/[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@]([H])(CCCC(O)=O)OO	2571.4	Standard non polar	33892256
(5S)-hydroperoxy-18-hydroxy-EPE	[H]\C(C\C([H])=C(\[H])C([H])=C([H])C([H])(O)CC)=C(/[H])C\C([H])=C(\[H])/C(/[H])=C(\[H])[C@]([H])(CCCC(O)=O)OO	2768.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(5S)-hydroperoxy-18-hydroxy-EPE,1TMS,isomer #1	CCC(C=C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)OO)O[Si](C)(C)C	3092.2	Semi standard non polar	33892256
(5S)-hydroperoxy-18-hydroxy-EPE,1TMS,isomer #2	CCC(O)C=C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)OO	3004.8	Semi standard non polar	33892256
(5S)-hydroperoxy-18-hydroxy-EPE,2TMS,isomer #1	CCC(C=C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)OO)O[Si](C)(C)C	3024.3	Semi standard non polar	33892256
(5S)-hydroperoxy-18-hydroxy-EPE,1TBDMS,isomer #1	CCC(C=C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)OO)O[Si](C)(C)C(C)(C)C	3341.1	Semi standard non polar	33892256
(5S)-hydroperoxy-18-hydroxy-EPE,1TBDMS,isomer #2	CCC(O)C=C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)OO	3247.0	Semi standard non polar	33892256
(5S)-hydroperoxy-18-hydroxy-EPE,2TBDMS,isomer #1	CCC(C=C/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)OO)O[Si](C)(C)C(C)(C)C	3505.7	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 - (5S)-hydroperoxy-18-hydroxy-EPE GC-MS (Non-derivatized) - 70eV, Positive	splash10-0564-4195000000-b5689d79dac325a286a7	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE GC-MS (2 TMS) - 70eV, Positive	splash10-05dr-9133700000-69681f9295690b08ac33	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 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 - (5S)-hydroperoxy-18-hydroxy-EPE 10V, Positive-QTOF	splash10-001i-0019000000-5a63c1859e9d6d4d2cbb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 20V, Positive-QTOF	splash10-0kv1-2196000000-1473b2dc4350824b9dea	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 40V, Positive-QTOF	splash10-001v-8890000000-961eddd30761611edd66	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 10V, Negative-QTOF	splash10-0002-0019000000-e89bb49bbb54281cf109	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 20V, Negative-QTOF	splash10-001s-3149000000-86cf972624d278c74247	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 40V, Negative-QTOF	splash10-0a4l-9041000000-8107e898d3fce3cca5da	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 10V, Positive-QTOF	splash10-0uyj-0069000000-b7ac50e1af23db87e977	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 20V, Positive-QTOF	splash10-0frt-1964000000-f3ea2c7785f6da30314e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 40V, Positive-QTOF	splash10-00o3-3900000000-0bf711bf496e67d1a1c5	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 10V, Negative-QTOF	splash10-0002-0009000000-119de936cb572c732081	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 20V, Negative-QTOF	splash10-052b-3069000000-1feaf8679af4d4e995ce	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5S)-hydroperoxy-18-hydroxy-EPE 40V, Negative-QTOF	splash10-0a4l-9150000000-2d78e1e2d6a574f617a0	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

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.

Showing metabocard for (5S)-hydroperoxy-18-hydroxy-EPE (HMDB0062616)

MOL for HMDB0062616 ((5S)-hydroperoxy-18-hydroxy-EPE)

3D MOL for HMDB0062616 ((5S)-hydroperoxy-18-hydroxy-EPE)

3D SDF for HMDB0062616 ((5S)-hydroperoxy-18-hydroxy-EPE)

3D-SDF for HMDB0062616 ((5S)-hydroperoxy-18-hydroxy-EPE)

PDB for HMDB0062616 ((5S)-hydroperoxy-18-hydroxy-EPE)

3D PDB for HMDB0062616 ((5S)-hydroperoxy-18-hydroxy-EPE)

SMILES for HMDB0062616 ((5S)-hydroperoxy-18-hydroxy-EPE)

INCHI for HMDB0062616 ((5S)-hydroperoxy-18-hydroxy-EPE)

Structure for HMDB0062616 ((5S)-hydroperoxy-18-hydroxy-EPE)

3D Structure for HMDB0062616 ((5S)-hydroperoxy-18-hydroxy-EPE)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra