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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-09-15 09:55:13 UTC

Update Date

2020-02-26 21:33:18 UTC

HMDB ID

HMDB0010217

Secondary Accession Numbers

HMDB10217

Metabolite Identification

Common Name

5-KETE

Description

5-KETE, also known as 5-keto-ete or 5-oxoete, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 5-KETE is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 5-KETE.

Structure

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

HMDB0010217
     RDKit          3D
5-KETE
 53 52  0  0  0  0  0  0  0  0999 V2000
   -6.9865    0.5318   -0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3123   -0.6409    0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0195   -0.4224    1.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6592   -0.2039    2.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8562    0.9532    1.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5683    0.9138    2.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    0.8022    1.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831    0.6972    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    1.8225   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1565    1.5518   -0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666    0.1830   -0.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920    0.0087   -2.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7635   -0.2678   -2.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9358   -0.4330   -1.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0904   -0.7164   -2.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3252   -0.8993   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817   -1.1598   -2.4564 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2965   -0.7704   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6109   -0.9101    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5785    0.1670   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8362   -0.0669    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6120   -0.9732    0.2065 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1531    0.6993    1.6740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9599    1.5051   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0868    0.4349   -1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8147    0.6968   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4311   -0.8054    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8851   -1.5945   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4282   -1.3199    2.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6649    0.4364    2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0037   -1.1218    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7276   -0.0634    3.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8281    0.9953    0.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3302    1.9415    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6846    0.9905    3.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287    0.7850    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132   -0.2893   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883    0.8812   -0.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6862    2.8693   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5203    2.3515   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745    0.1031   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158   -0.6340   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    0.1220   -2.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8126   -0.3728   -3.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9983   -0.3575   -0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -0.8063   -3.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6189   -1.5926   -0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8104    0.2198   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0480   -1.9241    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4475   -0.7333    1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292    0.2150   -1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1960    1.1755    0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9342    0.4423    2.6482 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  2  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
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 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 02241200332D          

 23 22  0  0  0  0            999 V2000
   12.9438  -13.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7857  -13.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6276  -13.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4695  -13.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3114  -13.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1533  -13.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9952  -13.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9952  -12.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8370  -11.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8370  -10.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1226  -10.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1226   -9.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4082   -9.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6937   -9.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8360   -9.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9793   -9.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5504   -9.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1215   -9.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2649   -9.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4071   -9.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2649  -10.4562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4071  -10.4562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6927   -9.2188    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010217

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\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/h6-7,9-10,12-14,16H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+

> <INCHI_KEY>
MEASLHGILYBXFO-XTDASVJISA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.24750509698268

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.85

> <JCHEM_LOGP>
5.767698232000001

> <ALOGPS_LOGS>
-5.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.426202526704581

> <JCHEM_PKA_STRONGEST_BASIC>
-4.588692612250522

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
100.57209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.21e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-Oxo-ETE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010217
     RDKit          3D
5-KETE
 53 52  0  0  0  0  0  0  0  0999 V2000
   -6.9865    0.5318   -0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3123   -0.6409    0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0195   -0.4224    1.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6592   -0.2039    2.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8562    0.9532    1.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5683    0.9138    2.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    0.8022    1.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831    0.6972    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    1.8225   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1565    1.5518   -0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666    0.1830   -0.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920    0.0087   -2.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7635   -0.2678   -2.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9358   -0.4330   -1.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0904   -0.7164   -2.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3252   -0.8993   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817   -1.1598   -2.4564 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2965   -0.7704   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6109   -0.9101    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5785    0.1670   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8362   -0.0669    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6120   -0.9732    0.2065 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1531    0.6993    1.6740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9599    1.5051   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0868    0.4349   -1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8147    0.6968   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4311   -0.8054    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8851   -1.5945   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4282   -1.3199    2.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6649    0.4364    2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0037   -1.1218    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7276   -0.0634    3.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8281    0.9953    0.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3302    1.9415    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6846    0.9905    3.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287    0.7850    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132   -0.2893   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883    0.8812   -0.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6862    2.8693   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5203    2.3515   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745    0.1031   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158   -0.6340   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    0.1220   -2.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8126   -0.3728   -3.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9983   -0.3575   -0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -0.8063   -3.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6189   -1.5926   -0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8104    0.2198   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0480   -1.9241    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4475   -0.7333    1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292    0.2150   -1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1960    1.1755    0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9342    0.4423    2.6482 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  2  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
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 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                                 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      24.162 -24.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.733 -25.457   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.305 -24.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.876 -25.457   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.448 -24.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.019 -25.457   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.591 -24.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.591 -22.735   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.162 -21.828   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.162 -20.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.829 -19.518   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.829 -17.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.495 -17.208   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.162 -17.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.827 -17.978   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.828 -17.208   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.161 -17.208   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.493 -17.208   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.494 -17.978   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.160 -17.978   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      28.494 -19.518   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      23.160 -19.518   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      21.826 -17.208   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   16                                                       
CONECT   15   17   18                                                       
CONECT   16   14   19                                                       
CONECT   17   15   19                                                       
CONECT   18   15   20                                                       
CONECT   19   16   17   21                                                  
CONECT   20   18   22   23                                                  
CONECT   21   19                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0010217
HETATM    1  C1  UNL     1      -6.986   0.532  -0.672  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.312  -0.641   0.190  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.019  -0.422   1.615  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.659  -0.204   2.097  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.856   0.953   1.611  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.568   0.914   2.332  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.416   0.802   1.765  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.183   0.697   0.317  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.309   1.822  -0.154  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.157   1.552  -0.671  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.367   0.183  -0.829  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.592   0.009  -2.295  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.763  -0.268  -2.781  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.936  -0.433  -1.985  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.090  -0.716  -2.606  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.325  -0.899  -1.861  1.00  0.00           C  
HETATM   17  O1  UNL     1       6.382  -1.160  -2.456  1.00  0.00           O  
HETATM   18  C17 UNL     1       5.296  -0.770  -0.397  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.611  -0.910   0.287  1.00  0.00           C  
HETATM   20  C19 UNL     1       7.579   0.167  -0.153  1.00  0.00           C  
HETATM   21  C20 UNL     1       8.836  -0.067   0.585  1.00  0.00           C  
HETATM   22  O2  UNL     1       9.612  -0.973   0.206  1.00  0.00           O  
HETATM   23  O3  UNL     1       9.153   0.699   1.674  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.960   1.505  -0.148  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.087   0.435  -1.291  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.815   0.697  -1.452  1.00  0.00           H  
HETATM   27  H4  UNL     1      -8.431  -0.805   0.075  1.00  0.00           H  
HETATM   28  H5  UNL     1      -6.885  -1.594  -0.213  1.00  0.00           H  
HETATM   29  H6  UNL     1      -7.428  -1.320   2.203  1.00  0.00           H  
HETATM   30  H7  UNL     1      -7.665   0.436   2.019  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.004  -1.122   2.028  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.728  -0.063   3.228  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.828   0.995   0.544  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.330   1.941   1.941  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.685   0.990   3.443  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.529   0.785   2.438  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.913  -0.289  -0.017  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.188   0.881  -0.199  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.686   2.869  -0.042  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.520   2.352  -1.034  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.375   0.103  -0.322  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.216  -0.634  -0.419  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.277   0.122  -2.980  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.813  -0.373  -3.880  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.998  -0.357  -0.940  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.088  -0.806  -3.676  1.00  0.00           H  
HETATM   47  H24 UNL     1       4.619  -1.593  -0.024  1.00  0.00           H  
HETATM   48  H25 UNL     1       4.810   0.220  -0.188  1.00  0.00           H  
HETATM   49  H26 UNL     1       7.048  -1.924   0.152  1.00  0.00           H  
HETATM   50  H27 UNL     1       6.448  -0.733   1.386  1.00  0.00           H  
HETATM   51  H28 UNL     1       7.729   0.215  -1.236  1.00  0.00           H  
HETATM   52  H29 UNL     1       7.196   1.175   0.139  1.00  0.00           H  
HETATM   53  H30 UNL     1       8.934   0.442   2.648  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   35
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   10   39
CONECT   10   11   40
CONECT   11   12   41   42
CONECT   12   13   13   43
CONECT   13   14   44
CONECT   14   15   15   45
CONECT   15   16   46
CONECT   16   17   17   18
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21   51   52
CONECT   21   22   22   23
CONECT   23   53
END

HMDB0010217
     RDKit          3D
5-KETE
 53 52  0  0  0  0  0  0  0  0999 V2000
   -6.9865    0.5318   -0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3123   -0.6409    0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0195   -0.4224    1.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6592   -0.2039    2.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8562    0.9532    1.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5683    0.9138    2.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    0.8022    1.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831    0.6972    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    1.8225   -0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1565    1.5518   -0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666    0.1830   -0.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920    0.0087   -2.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7635   -0.2678   -2.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9358   -0.4330   -1.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0904   -0.7164   -2.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3252   -0.8993   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817   -1.1598   -2.4564 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2965   -0.7704   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6109   -0.9101    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5785    0.1670   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8362   -0.0669    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6120   -0.9732    0.2065 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1531    0.6993    1.6740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9599    1.5051   -0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0868    0.4349   -1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8147    0.6968   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4311   -0.8054    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8851   -1.5945   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4282   -1.3199    2.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6649    0.4364    2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0037   -1.1218    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7276   -0.0634    3.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8281    0.9953    0.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3302    1.9415    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6846    0.9905    3.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287    0.7850    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132   -0.2893   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883    0.8812   -0.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6862    2.8693   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5203    2.3515   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745    0.1031   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158   -0.6340   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    0.1220   -2.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8126   -0.3728   -3.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9983   -0.3575   -0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -0.8063   -3.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6189   -1.5926   -0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8104    0.2198   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0480   -1.9241    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4475   -0.7333    1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292    0.2150   -1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1960    1.1755    0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9342    0.4423    2.6482 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  2  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
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 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
(6E,8Z,11Z,14Z)-5-Oxoicosa-6,8,11,14-tetraenoic acid	ChEBI
5-Keto-ete	ChEBI
5-Ketoeicosatetraenoic acid	ChEBI
5-oxo, 6t,8C,11C,14C-20:4	ChEBI
5-oxo-6(e),8(Z),11(Z),14(Z)-Eicosatetraenoic acid	ChEBI
5-oxo-6E,8Z,11Z,14Z-Eicosatetraenoic acid	ChEBI
5-oxo-Icosa-6,8,11,14-tetraenoic acid	ChEBI
5-Oxoeicosatetraenoic acid	ChEBI
5-OxoETE	ChEBI
5-Oxoicosatetraenoic acid	ChEBI
Eicosa-5,8,12,14-tetraenoic acid	ChEBI
(6E,8Z,11Z,14Z)-5-Oxoicosa-6,8,11,14-tetraenoate	Generator
5-Ketoeicosatetraenoate	Generator
5-oxo-6(e),8(Z),11(Z),14(Z)-Eicosatetraenoate	Generator
5-oxo-6E,8Z,11Z,14Z-Eicosatetraenoate	Generator
5-oxo-Icosa-6,8,11,14-tetraenoate	Generator
5-Oxoeicosatetraenoate	Generator
5-Oxoicosatetraenoate	Generator
Eicosa-5,8,12,14-tetraenoate	Generator
5-Keto-6,8,11,14-eicosatetraenoate	HMDB
5-Keto-6,8,11,14-eicosatetraenoic acid	HMDB
5-oxo-6,8,11,14-Eicosatetraenoate	HMDB
5-oxo-6,8,11,14-Eicosatetraenoic acid	HMDB
5-oxo-Eicosatetraenoate	HMDB
5-oxo-Eicosatetraenoic acid	HMDB
5-oxo-6,8,11,14-ETE	HMDB
5-oxo-6,8,11,14-Eicosatetraenoic acid, e,Z,Z,Z isomer	HMDB

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

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

Traditional Name

5-Oxo-ETE

CAS Registry Number

126432-17-5

SMILES

CCCCC\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/h6-7,9-10,12-14,16H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+

InChI Key

MEASLHGILYBXFO-XTDASVJISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxoicosatetraenoic acid (CHEBI:52449 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C14732 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060011 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Cellular substructure

Membrane (HMDB: HMDB0010217)

Source

Endogenous

Endogenous (HMDB: HMDB0010217)

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

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	0.00062 g/L	ALOGPS
logP	5.85	ALOGPS
logP	5.77	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.43	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	100.57 m³·mol⁻¹	ChemAxon
Polarizability	37.25 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
DeepCCS	[M+H]+	191.284	30932474
DeepCCS	[M-H]-	188.926	30932474
DeepCCS	[M-2H]-	221.812	30932474
DeepCCS	[M+Na]+	197.377	30932474
AllCCS	[M+H]+	185.2	32859911
AllCCS	[M+H-H2O]+	182.3	32859911
AllCCS	[M+NH4]+	187.9	32859911
AllCCS	[M+Na]+	188.7	32859911
AllCCS	[M-H]-	184.9	32859911
AllCCS	[M+Na-2H]-	186.6	32859911
AllCCS	[M+HCOO]-	188.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.56 minutes	32390414
Predicted by Siyang on May 30, 2022	22.975 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.71 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3012.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	545.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	225.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	363.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	654.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1061.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	618.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2204.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	716.8 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	1741.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	770.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	517.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	359.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	551.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-KETE	CCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=O	4190.4	Standard polar	33892256
5-KETE	CCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=O	2348.1	Standard non polar	33892256
5-KETE	CCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=O	2642.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-KETE,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C=C\C(=O)CCCC(=O)O[Si](C)(C)C	2654.6	Semi standard non polar	33892256
5-KETE,1TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O)O[Si](C)(C)C	2859.6	Semi standard non polar	33892256
5-KETE,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2800.1	Semi standard non polar	33892256
5-KETE,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2710.0	Standard non polar	33892256
5-KETE,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2848.1	Standard polar	33892256
5-KETE,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C=C\C(=O)CCCC(=O)O[Si](C)(C)C(C)(C)C	2912.1	Semi standard non polar	33892256
5-KETE,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C=C\C(=CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3102.9	Semi standard non polar	33892256
5-KETE,2TBDMS,isomer #1	CCCCC/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	3271.6	Semi standard non polar	33892256
5-KETE,2TBDMS,isomer #1	CCCCC/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	3098.3	Standard non polar	33892256
5-KETE,2TBDMS,isomer #1	CCCCC/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	2931.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-KETE GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-6490000000-f7442bdfafe15fcbd8be	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-KETE GC-MS (1 TMS) - 70eV, Positive	splash10-00gr-9334000000-c55c3efafdce8f7f48c8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-KETE GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-KETE 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOF	splash10-014i-0019000000-cc3fc8fe0ef27f29f3fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOF	splash10-014i-0019000000-73c8527e54e3481ad1a3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOF	splash10-014i-0039000000-0e2010fcd9ac17c6d0ee	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOF	splash10-014i-0189000000-5eba1c071b73ab160906	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOF	splash10-0v4j-0193000000-5251b2d0521f18bf6cdc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOF	splash10-0udi-0192000000-69bb1f0b8710630e3498	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOF	splash10-0udi-0293000000-1ebf2792695803c02d99	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOF	splash10-0udi-0493000000-6710e8cf7a82b74bf8e9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-KETE LC-ESI-QIT , negative-QTOF	splash10-0ika-1890000000-3ca3507e7352ecaba473	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 10V, Positive-QTOF	splash10-0udi-0139000000-56d3e500a2215f16ddba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 20V, Positive-QTOF	splash10-0ul9-7893000000-95b152324d0f205b491b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 40V, Positive-QTOF	splash10-0006-7960000000-b0a8aa3380cadece0d37	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 10V, Negative-QTOF	splash10-014i-0049000000-8a20eefad5150c79b650	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 20V, Negative-QTOF	splash10-00kb-1093000000-57fbe7ca052d52fe8cbb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 40V, Negative-QTOF	splash10-052f-8190000000-ad8a838b30e7500809fa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 10V, Positive-QTOF	splash10-0uxr-1629000000-b0fafb9cc5aaed98cdc5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 20V, Positive-QTOF	splash10-0f89-5944000000-fd1af71047782189494e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 40V, Positive-QTOF	splash10-00lu-9700000000-cde9bfbce3fdd2d8c1b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 10V, Negative-QTOF	splash10-014i-0009000000-ac8d7382f0841f88fc4e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 20V, Negative-QTOF	splash10-014i-6297000000-81cdd06d01b88c7801f6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-KETE 40V, Negative-QTOF	splash10-052f-9580000000-e2e6654123cbfb72d902	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood

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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000136 +/- 0.000018 ) uM	Adult (>18 years old)	Not Specified	Normal	18953024	details
Blood	Detected and Quantified	0.000136 +/- 0.000018 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000145 +/- 0.00012 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

FDB027371

KNApSAcK ID

Not Available

Chemspider ID

4446283

KEGG Compound ID

C14732

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

KETE

METLIN ID

Not Available

PubChem Compound

5283159

PDB ID

Not Available

ChEBI ID

52449

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

Patel P, Cossette C, Anumolu JR, Gravel S, Lesimple A, Mamer OA, Rokach J, Powell WS: Structural requirements for activation of the 5-oxo-6E,8Z, 11Z,14Z-eicosatetraenoic acid (5-oxo-ETE) receptor: identification of a mead acid metabolite with potent agonist activity. J Pharmacol Exp Ther. 2008 May;325(2):698-707. doi: 10.1124/jpet.107.134908. Epub 2008 Feb 21. [PubMed:18292294 ]

Showing metabocard for 5-KETE (HMDB0010217)

MOL for HMDB0010217 (5-KETE)

3D MOL for HMDB0010217 (5-KETE)

3D SDF for HMDB0010217 (5-KETE)

3D-SDF for HMDB0010217 (5-KETE)

PDB for HMDB0010217 (5-KETE)

3D PDB for HMDB0010217 (5-KETE)

SMILES for HMDB0010217 (5-KETE)

INCHI for HMDB0010217 (5-KETE)

Structure for HMDB0010217 (5-KETE)

3D Structure for HMDB0010217 (5-KETE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra