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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-25 10:38:58 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005081

Secondary Accession Numbers

HMDB05081

Metabolite Identification

Common Name

5-HEPE

Description

5-HEPE is a major eicosanoid formed from eicosapentaenoic acid (EPA). 5-HEPE is produced in human neutrophils. The eicosanoids are a diverse family of molecules that have powerful effects on cell function. They are best known as intercellular messengers, having autocrine and paracrine effects following their secretion from the cells that synthesize them. The diversity of possible products that can be synthesized from eicosatrienoic acid is due, in part to the variety of enzymes that can act on it. Studies have placed many, but not all, of these enzymes at or inside the nucleus. In some cases, the nuclear import or export of eicosatrienoic acid-processing enzymes is highly regulated. Furthermore, nuclear receptors that are activated by specific eicosanoids are known to exist. (PMID: 8847485 , 15896193 ).

Structure

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

HMDB0005081
     RDKit          3D
5-HEPE
 53 52  0  0  0  0  0  0  0  0999 V2000
   -9.3321    0.6535   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4983   -0.3829   -0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6482   -1.1212   -1.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3469   -1.1410   -1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5843   -0.4262   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7394   -1.3232    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4429   -1.1471    0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867   -0.0845    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7302   -0.8161   -0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4540   -0.6554   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1590    0.2578    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0463   -0.4998    1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116   -0.2634    1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9698    0.7818    0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2784    0.9417    0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712    2.0169    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9725    3.2242    0.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4080    1.5118   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2514    0.2390   -0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5288   -0.4291   -1.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2566   -0.8332   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7946   -0.6794    1.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5279   -1.4147   -0.2304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5634    1.2529   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8614    1.2785   -0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9966    0.1400   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2122   -1.0945    0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0314    0.1972    0.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1813   -1.6911   -1.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8424   -1.7402   -1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9891    0.3275   -0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2896    0.0354    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2359   -2.1360    1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -1.8589    1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127    0.5795   -0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108    0.6008    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018   -1.5222   -1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2465   -1.1970   -1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4904    0.8559    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117    1.0118   -0.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -1.3011    1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447   -0.9046    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4688    1.4099   -0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453    0.3426    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736    2.2020   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372    3.2644    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921    2.2794   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7918    1.3158    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6754   -0.4657   -0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5994    0.4220   -1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1650    0.1931   -1.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2643   -1.3271   -1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3091   -0.8797    0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 23 53  1  0
M  END


  Mrv0541 02231220212D          

 23 22  0  0  0  0            999 V2000
   18.8103   -7.7095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3827   -6.4719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6682   -7.7095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5247   -6.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2392   -6.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8103   -6.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9537   -6.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0957   -6.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6682   -6.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3813   -6.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6668   -6.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9523   -7.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9523   -6.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9523   -9.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2378   -8.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3813  -10.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2378   -8.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9523  -10.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6668  -10.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0957  -10.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3813  -11.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0957  -11.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3813  -12.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 13  2  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 14 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 17  2  0  0  0  0
 16 19  1  0  0  0  0
 16 20  1  0  0  0  0
 18 19  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005081

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+

> <INCHI_KEY>
FTAGQROYQYQRHF-FCWZHQICSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.169796242122416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid

> <ALOGPS_LOGP>
5.54

> <JCHEM_LOGP>
4.994438087333332

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.865306513915215

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.584101629727195

> <JCHEM_PKA_STRONGEST_BASIC>
-1.545515302673174

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
102.58610000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.86e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxyeicosapentaenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005081
     RDKit          3D
5-HEPE
 53 52  0  0  0  0  0  0  0  0999 V2000
   -9.3321    0.6535   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4983   -0.3829   -0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6482   -1.1212   -1.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3469   -1.1410   -1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5843   -0.4262   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7394   -1.3232    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4429   -1.1471    0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867   -0.0845    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7302   -0.8161   -0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4540   -0.6554   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1590    0.2578    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0463   -0.4998    1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116   -0.2634    1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9698    0.7818    0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2784    0.9417    0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712    2.0169    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9725    3.2242    0.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4080    1.5118   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2514    0.2390   -0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5288   -0.4291   -1.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2566   -0.8332   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7946   -0.6794    1.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5279   -1.4147   -0.2304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5634    1.2529   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8614    1.2785   -0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9966    0.1400   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2122   -1.0945    0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0314    0.1972    0.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1813   -1.6911   -1.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8424   -1.7402   -1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9891    0.3275   -0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2896    0.0354    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2359   -2.1360    1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -1.8589    1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127    0.5795   -0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108    0.6008    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018   -1.5222   -1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2465   -1.1970   -1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4904    0.8559    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117    1.0118   -0.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -1.3011    1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447   -0.9046    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4688    1.4099   -0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453    0.3426    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736    2.2020   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372    3.2644    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921    2.2794   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7918    1.3158    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6754   -0.4657   -0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5994    0.4220   -1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1650    0.1931   -1.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2643   -1.3271   -1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3091   -0.8797    0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 23 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      35.113 -14.391   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      41.781 -12.081   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      40.447 -14.391   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      36.446 -12.081   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      37.780 -12.851   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.113 -12.851   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      39.114 -12.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.779 -12.081   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      40.447 -12.851   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.445 -12.851   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.111 -12.081   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.778 -14.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.778 -12.851   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.778 -17.471   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.444 -15.161   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.445 -19.011   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.444 -16.701   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.778 -19.011   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.111 -19.781   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.779 -19.781   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.445 -22.091   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.779 -21.321   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.445 -23.631   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    1    4    8                                                  
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    2    3    7                                                  
CONECT   10    8   11                                                       
CONECT   11   10   13                                                       
CONECT   12   13   15                                                       
CONECT   13   11   12                                                       
CONECT   14   17   18                                                       
CONECT   15   12   17                                                       
CONECT   16   19   20                                                       
CONECT   17   14   15                                                       
CONECT   18   14   19                                                       
CONECT   19   16   18                                                       
CONECT   20   16   22                                                       
CONECT   21   22   23                                                       
CONECT   22   20   21                                                       
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0005081
HETATM    1  C1  UNL     1      -9.332   0.654  -0.957  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.498  -0.383  -0.158  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.648  -1.121  -1.102  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.347  -1.141  -1.034  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.584  -0.426  -0.002  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.739  -1.323   0.805  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.443  -1.147   0.841  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.687  -0.085   0.117  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.730  -0.816  -0.758  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.454  -0.655  -0.655  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.159   0.258   0.327  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.046  -0.500   1.240  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.312  -0.263   1.382  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.970   0.782   0.645  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.278   0.942   0.868  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.971   2.017   0.113  1.00  0.00           C  
HETATM   17  O1  UNL     1       4.973   3.224   0.802  1.00  0.00           O  
HETATM   18  C17 UNL     1       6.408   1.512  -0.113  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.251   0.239  -0.901  1.00  0.00           C  
HETATM   20  C19 UNL     1       7.529  -0.429  -1.246  1.00  0.00           C  
HETATM   21  C20 UNL     1       8.257  -0.833  -0.032  1.00  0.00           C  
HETATM   22  O2  UNL     1       7.795  -0.679   1.113  1.00  0.00           O  
HETATM   23  O3  UNL     1       9.528  -1.415  -0.230  1.00  0.00           O  
HETATM   24  H1  UNL     1      -8.563   1.253  -1.515  1.00  0.00           H  
HETATM   25  H2  UNL     1      -9.861   1.279  -0.226  1.00  0.00           H  
HETATM   26  H3  UNL     1      -9.997   0.140  -1.661  1.00  0.00           H  
HETATM   27  H4  UNL     1      -9.212  -1.095   0.340  1.00  0.00           H  
HETATM   28  H5  UNL     1      -8.031   0.197   0.623  1.00  0.00           H  
HETATM   29  H6  UNL     1      -8.181  -1.691  -1.918  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.842  -1.740  -1.816  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.989   0.327  -0.509  1.00  0.00           H  
HETATM   32  H9  UNL     1      -6.290   0.035   0.733  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.236  -2.136   1.368  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.861  -1.859   1.470  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.313   0.579  -0.502  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.211   0.601   0.850  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.102  -1.522  -1.525  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.246  -1.197  -1.302  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.490   0.856   0.949  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.712   1.012  -0.304  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.542  -1.301   1.806  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.845  -0.905   2.095  1.00  0.00           H  
HETATM   43  H20 UNL     1       2.469   1.410  -0.044  1.00  0.00           H  
HETATM   44  H21 UNL     1       4.845   0.343   1.554  1.00  0.00           H  
HETATM   45  H22 UNL     1       4.474   2.202  -0.883  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.237   3.264   1.488  1.00  0.00           H  
HETATM   47  H24 UNL     1       6.992   2.279  -0.660  1.00  0.00           H  
HETATM   48  H25 UNL     1       6.792   1.316   0.892  1.00  0.00           H  
HETATM   49  H26 UNL     1       5.675  -0.466  -0.249  1.00  0.00           H  
HETATM   50  H27 UNL     1       5.599   0.422  -1.786  1.00  0.00           H  
HETATM   51  H28 UNL     1       8.165   0.193  -1.923  1.00  0.00           H  
HETATM   52  H29 UNL     1       7.264  -1.327  -1.877  1.00  0.00           H  
HETATM   53  H30 UNL     1      10.309  -0.880   0.119  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    4   29
CONECT    4    5   30
CONECT    5    6   31   32
CONECT    6    7    7   33
CONECT    7    8   34
CONECT    8    9   35   36
CONECT    9   10   10   37
CONECT   10   11   38
CONECT   11   12   39   40
CONECT   12   13   13   41
CONECT   13   14   42
CONECT   14   15   15   43
CONECT   15   16   44
CONECT   16   17   18   45
CONECT   17   46
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21   51   52
CONECT   21   22   22   23
CONECT   23   53
END

HMDB0005081
     RDKit          3D
5-HEPE
 53 52  0  0  0  0  0  0  0  0999 V2000
   -9.3321    0.6535   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4983   -0.3829   -0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6482   -1.1212   -1.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3469   -1.1410   -1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5843   -0.4262   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7394   -1.3232    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4429   -1.1471    0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867   -0.0845    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7302   -0.8161   -0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4540   -0.6554   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1590    0.2578    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0463   -0.4998    1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116   -0.2634    1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9698    0.7818    0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2784    0.9417    0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712    2.0169    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9725    3.2242    0.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4080    1.5118   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2514    0.2390   -0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5288   -0.4291   -1.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2566   -0.8332   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7946   -0.6794    1.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5279   -1.4147   -0.2304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5634    1.2529   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8614    1.2785   -0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9966    0.1400   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2122   -1.0945    0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0314    0.1972    0.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1813   -1.6911   -1.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8424   -1.7402   -1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9891    0.3275   -0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2896    0.0354    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2359   -2.1360    1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -1.8589    1.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127    0.5795   -0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108    0.6008    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018   -1.5222   -1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2465   -1.1970   -1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4904    0.8559    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117    1.0118   -0.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -1.3011    1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447   -0.9046    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4688    1.4099   -0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453    0.3426    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736    2.2020   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372    3.2644    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921    2.2794   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7918    1.3158    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6754   -0.4657   -0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5994    0.4220   -1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1650    0.1931   -1.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2643   -1.3271   -1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3091   -0.8797    0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 23 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-5-HEPE	ChEBI
(+-)-5-Hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid	ChEBI
(+-)-5-Hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoate	Generator
(+/-)-5-hepe	HMDB
(+/-)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoate	HMDB
(+/-)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid	HMDB
5-Hydroxy-6,8,11,14,17-eicosapentaenoate	HMDB
5-Hydroxy-6,8,11,14,17-eicosapentaenoic acid	HMDB
5-Hydroxyeicosapentaenoate	HMDB
5-Hydroxyeicosapentaenoic acid	HMDB
5-HEPE	MeSH

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

(6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid

Traditional Name

5-hydroxyeicosapentaenoic acid

CAS Registry Number

92008-51-0

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)CCCC(O)=O

InChI Identifier

InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+

InChI Key

FTAGQROYQYQRHF-FCWZHQICSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosapentaenoic acids

Alternative Parents

Substituents

Hydroxyeicosapentaenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

HEPE (CHEBI:72801 )
Hydroxy/hydroperoxyeicosapentaenoic acids (LMFA03070027 )

Ontology

Not Available

Non-excretory biofluid

Blood (PMID: 18953024)

Cellular substructure

Extracellular (HMDB: HMDB0005081)
Membrane (HMDB: HMDB0005081)

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)

Process

Not Available

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	0.0029 g/L	ALOGPS
logP	5.54	ALOGPS
logP	4.99	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	102.59 m³·mol⁻¹	ChemAxon
Polarizability	37.17 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]+	186.181	31661259
DarkChem	[M-H]-	187.027	31661259
DeepCCS	[M+H]+	184.312	30932474
DeepCCS	[M-H]-	181.954	30932474
DeepCCS	[M-2H]-	214.841	30932474
DeepCCS	[M+Na]+	190.405	30932474
AllCCS	[M+H]+	185.6	32859911
AllCCS	[M+H-H2O]+	182.6	32859911
AllCCS	[M+NH4]+	188.4	32859911
AllCCS	[M+Na]+	189.2	32859911
AllCCS	[M-H]-	183.6	32859911
AllCCS	[M+Na-2H]-	185.3	32859911
AllCCS	[M+HCOO]-	187.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-HEPE	CC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)CCCC(O)=O	4339.3	Standard polar	33892256
5-HEPE	CC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)CCCC(O)=O	2377.1	Standard non polar	33892256
5-HEPE	CC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)CCCC(O)=O	2567.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-HEPE,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O)O[Si](C)(C)C	2805.4	Semi standard non polar	33892256
5-HEPE,1TMS,isomer #2	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(O)CCCC(=O)O[Si](C)(C)C	2643.5	Semi standard non polar	33892256
5-HEPE,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2709.7	Semi standard non polar	33892256
5-HEPE,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3040.8	Semi standard non polar	33892256
5-HEPE,1TBDMS,isomer #2	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(O)CCCC(=O)O[Si](C)(C)C(C)(C)C	2889.7	Semi standard non polar	33892256
5-HEPE,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3188.1	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 - 5-HEPE GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-5394000000-3c896430e353b0ced0db	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-HEPE GC-MS (2 TMS) - 70eV, Positive	splash10-0umj-8209200000-58c4694ad173b557f3c5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-HEPE 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 - 5-HEPE 10V, Positive-QTOF	splash10-0udi-0149000000-dfe33b6babf270b34752	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 20V, Positive-QTOF	splash10-0udu-5693000000-fb5c896d30ace0c553d8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 40V, Positive-QTOF	splash10-000l-9880000000-5d7665b416fe42c2c371	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 10V, Negative-QTOF	splash10-014i-0069000000-023fef6c61163c7bc817	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 20V, Negative-QTOF	splash10-00kb-2093000000-e62551450dc40c949d52	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 40V, Negative-QTOF	splash10-0a4l-9160000000-b435064b3bb6876f2d7b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 10V, Negative-QTOF	splash10-014i-0019000000-816e1c2de0c22c09572d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 20V, Negative-QTOF	splash10-066r-5298000000-38dbc1cf2b56e0e1e6ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 40V, Negative-QTOF	splash10-052g-9650000000-5f5552a443dffc55be3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 10V, Positive-QTOF	splash10-0ue9-1549000000-3a0bdd92ab4130f1a2cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 20V, Positive-QTOF	splash10-001i-4932000000-a4abea64aa118c0599d7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-HEPE 40V, Positive-QTOF	splash10-003u-9500000000-f8f2e81a65d2e71229cf	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)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00067 +/- 0.000121 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.000863 +/- 0.000404 uM	Adult (>18 years old)	Not Specified	Normal	18953024	details
Blood	Detected and Quantified	0.00115 +/- 0.00014 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000228 +/- 0.000091 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

FDB023620

KNApSAcK ID

Not Available

Chemspider ID

4944072

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439678

PDB ID

Not Available

ChEBI ID

72801

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

Powell WS, Gravel S, Gravelle F: Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils. J Lipid Res. 1995 Dec;36(12):2590-8. [PubMed:8847485 ]
Charbeneau RP, Peters-Golden M: Eicosanoids: mediators and therapeutic targets in fibrotic lung disease. Clin Sci (Lond). 2005 Jun;108(6):479-91. [PubMed:15896193 ]
Lipid Maps (LMFA03070010) [Link]

Showing metabocard for 5-HEPE (HMDB0005081)

MOL for HMDB0005081 (5-HEPE)

3D MOL for HMDB0005081 (5-HEPE)

3D SDF for HMDB0005081 (5-HEPE)

3D-SDF for HMDB0005081 (5-HEPE)

PDB for HMDB0005081 (5-HEPE)

3D PDB for HMDB0005081 (5-HEPE)

SMILES for HMDB0005081 (5-HEPE)

INCHI for HMDB0005081 (5-HEPE)

Structure for HMDB0005081 (5-HEPE)

3D Structure for HMDB0005081 (5-HEPE)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra