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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 06:28:20 UTC

Update Date

2022-03-07 02:49:19 UTC

HMDB ID

HMDB0003876

Secondary Accession Numbers

HMDB0002110
HMDB02110
HMDB03876

Metabolite Identification

Common Name

15-HETE

Description

15-HETE is a hydroxyeicosatetraenoic acid. Hydroxyeicosatetraenoic acids (HETEs) are formed by the 5-, 12-, and 15-lipoxygenase (LO) pathways. The 5- and 12-LO products are mainly proinflammatory in the skin whereas the main 15-LO product 15-HETE has antiinflammatory capacities. In vitro, 15-HETE has been shown to inhibit LTB4 formation, 12-HETE formation, and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5-LO because no changes in PGE2 formation have been determined. In vivo, 15-HETE inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. 15-HETE also has some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells (PMID: 11104340 ). 15(S)-HETE is found to be associated with Zellweger syndrome, which is an inborn error of metabolism.

Structure

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

HMDB0003876
     RDKit          3D
15-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
    7.9075    0.5885   -2.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1007    0.2727   -0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3553    1.5133   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688    1.1824    0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943    0.0917    0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782    0.4038   -0.5712 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8085    1.5162   -0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7525   -0.7881   -0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177   -0.9126   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389   -2.0916   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4617   -2.3648   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459   -1.4295    0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -2.0785    1.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7634   -2.1900    2.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9569   -1.7790    1.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0280   -1.1600    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5119    0.0628    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0480    0.9755    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4717    1.3826    1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9704    2.0271   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0029    1.0963   -1.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9314   -0.1415   -1.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1147    1.6027   -2.6683 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2436    0.6557   -3.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117    1.5435   -2.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6033   -0.2560   -2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4257   -0.5682   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8145   -0.0012   -0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0913    2.3188   -0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6740    1.9202   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2407    0.8589    1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9929    2.0678    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9857   -0.0557    1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0478   -0.9053    0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1050    0.7097   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6663    1.6226    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300   -1.5632   -1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -0.0974    0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1876   -2.8347   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9754   -3.2930   -0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.7232    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8079   -0.7103    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001   -2.4732    2.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9036   -2.7029    3.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5763   -1.1230    2.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7129   -2.6937    1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6855   -1.7206   -0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4340    0.3678   -0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7165    0.7566    2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4730    1.9829    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6518    2.1436    1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1642    0.4985    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0329    2.3351   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3635    2.9448   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3565    0.9457   -3.3941 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  1  0
  6  8  1  0
  8  9  2  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  1  0
 16 17  2  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
  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  6
  7 36  1  0
  8 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
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END


  Mrv1652310111917212D          

 23 22  0  0  0  0            999 V2000
10009.684010006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.968610006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.255210006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.428510006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.715110006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.000110006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.174810006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.460110006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.745610006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.920210006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.205610006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.491110006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.776410006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.061610006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.344910006.4340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.061610007.6707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.399510006.4340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10011.112810006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.828210006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.541610006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.257110006.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.974510006.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.399510005.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 17 18  1  0  0  0  0
 17 23  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003876

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1

> <INCHI_KEY>
JSFATNQSLKRBCI-VAEKSGALSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.149109802165796

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid

> <ALOGPS_LOGP>
5.82

> <JCHEM_LOGP>
5.356359744

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677863984817

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819772015121311

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759706768920925

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.46950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.95e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15 hete

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003876
     RDKit          3D
15-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
    7.9075    0.5885   -2.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1007    0.2727   -0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3553    1.5133   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688    1.1824    0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943    0.0917    0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782    0.4038   -0.5712 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8085    1.5162   -0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7525   -0.7881   -0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177   -0.9126   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389   -2.0916   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4617   -2.3648   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459   -1.4295    0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -2.0785    1.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7634   -2.1900    2.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9569   -1.7790    1.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0280   -1.1600    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5119    0.0628    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0480    0.9755    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4717    1.3826    1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9704    2.0271   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0029    1.0963   -1.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9314   -0.1415   -1.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1147    1.6027   -2.6683 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2436    0.6557   -3.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117    1.5435   -2.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6033   -0.2560   -2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4257   -0.5682   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8145   -0.0012   -0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0913    2.3188   -0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6740    1.9202   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2407    0.8589    1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9929    2.0678    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9857   -0.0557    1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0478   -0.9053    0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1050    0.7097   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6663    1.6226    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300   -1.5632   -1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -0.0974    0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1876   -2.8347   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9754   -3.2930   -0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.7232    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8079   -0.7103    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001   -2.4732    2.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9036   -2.7029    3.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5763   -1.1230    2.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7129   -2.6937    1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6855   -1.7206   -0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4340    0.3678   -0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7165    0.7566    2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4730    1.9829    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6518    2.1436    1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1642    0.4985    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0329    2.3351   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3635    2.9448   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3565    0.9457   -3.3941 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  1  0
  6  8  1  0
  8  9  2  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  1  0
 16 17  2  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
  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  6
  7 36  1  0
  8 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
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 11-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-19         0                                  
HETATM    1  C   UNK     0    8684.7438679.446   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8683.4088678.677   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8682.0768679.446   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8680.5338679.446   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8679.2028678.677   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8677.8678679.446   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8676.3268679.446   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8674.9928678.677   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.6588679.446   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8672.1188679.446   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8670.7848678.677   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.4508679.446   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.1168678.677   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.7828679.446   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8665.4448678.677   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8666.7828680.985   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8686.0798678.677   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8687.4118679.446   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8688.7468678.677   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8690.0788679.446   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8691.4138678.677   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8692.7528679.446   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8686.0798677.136   0.000  0.00  0.00           O+0
CONECT    1    2   17                                                       
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   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    1   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0003876
HETATM    1  C1  UNL     1       7.908   0.588  -2.196  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.101   0.273  -0.939  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.355   1.513  -0.474  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.569   1.182   0.769  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.594   0.092   0.498  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.578   0.404  -0.571  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.808   1.516  -0.231  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.753  -0.788  -0.885  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.518  -0.913  -0.357  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.739  -2.092  -0.686  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.462  -2.365  -0.260  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.146  -1.429   0.648  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.529  -2.079   1.928  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.763  -2.190   2.278  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.957  -1.779   1.616  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.028  -1.160   0.327  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.512   0.063   0.068  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.048   0.976   1.060  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.472   1.383   1.008  1.00  0.00           C  
HETATM   20  C19 UNL     1      -6.970   2.027  -0.239  1.00  0.00           C  
HETATM   21  C20 UNL     1      -7.003   1.096  -1.370  1.00  0.00           C  
HETATM   22  O2  UNL     1      -6.931  -0.142  -1.166  1.00  0.00           O  
HETATM   23  O3  UNL     1      -7.115   1.603  -2.668  1.00  0.00           O  
HETATM   24  H1  UNL     1       7.244   0.656  -3.084  1.00  0.00           H  
HETATM   25  H2  UNL     1       8.412   1.543  -2.053  1.00  0.00           H  
HETATM   26  H3  UNL     1       8.603  -0.256  -2.345  1.00  0.00           H  
HETATM   27  H4  UNL     1       6.426  -0.568  -1.125  1.00  0.00           H  
HETATM   28  H5  UNL     1       7.815  -0.001  -0.160  1.00  0.00           H  
HETATM   29  H6  UNL     1       7.091   2.319  -0.187  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.674   1.920  -1.240  1.00  0.00           H  
HETATM   31  H8  UNL     1       6.241   0.859   1.598  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.993   2.068   1.114  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.986  -0.056   1.445  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.048  -0.905   0.306  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.105   0.710  -1.522  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.666   1.623   0.726  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.130  -1.563  -1.534  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.232  -0.097   0.264  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.188  -2.835  -1.356  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.975  -3.293  -0.571  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.284  -0.723   1.028  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.808  -0.710   0.219  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.700  -2.473   2.587  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.904  -2.703   3.281  1.00  0.00           H  
HETATM   45  H22 UNL     1      -4.576  -1.123   2.330  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.713  -2.694   1.587  1.00  0.00           H  
HETATM   47  H24 UNL     1      -3.686  -1.721  -0.572  1.00  0.00           H  
HETATM   48  H25 UNL     1      -4.434   0.368  -0.998  1.00  0.00           H  
HETATM   49  H26 UNL     1      -4.716   0.757   2.119  1.00  0.00           H  
HETATM   50  H27 UNL     1      -4.473   1.983   0.899  1.00  0.00           H  
HETATM   51  H28 UNL     1      -6.652   2.144   1.836  1.00  0.00           H  
HETATM   52  H29 UNL     1      -7.164   0.499   1.201  1.00  0.00           H  
HETATM   53  H30 UNL     1      -8.033   2.335  -0.058  1.00  0.00           H  
HETATM   54  H31 UNL     1      -6.364   2.945  -0.501  1.00  0.00           H  
HETATM   55  H32 UNL     1      -7.357   0.946  -3.394  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    8   35
CONECT    7   36
CONECT    8    9    9   37
CONECT    9   10   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   45   46
CONECT   16   17   17   47
CONECT   17   18   48
CONECT   18   19   49   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   22   23
CONECT   23   55
END

HMDB0003876
     RDKit          3D
15-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
    7.9075    0.5885   -2.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1007    0.2727   -0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3553    1.5133   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688    1.1824    0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943    0.0917    0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782    0.4038   -0.5712 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8085    1.5162   -0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7525   -0.7881   -0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177   -0.9126   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389   -2.0916   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4617   -2.3648   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1459   -1.4295    0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -2.0785    1.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7634   -2.1900    2.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9569   -1.7790    1.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0280   -1.1600    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5119    0.0628    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0480    0.9755    1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4717    1.3826    1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9704    2.0271   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0029    1.0963   -1.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9314   -0.1415   -1.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1147    1.6027   -2.6683 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2436    0.6557   -3.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117    1.5435   -2.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6033   -0.2560   -2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4257   -0.5682   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8145   -0.0012   -0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0913    2.3188   -0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6740    1.9202   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2407    0.8589    1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9929    2.0678    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9857   -0.0557    1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0478   -0.9053    0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1050    0.7097   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6663    1.6226    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300   -1.5632   -1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -0.0974    0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1876   -2.8347   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9754   -3.2930   -0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.7232    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8079   -0.7103    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001   -2.4732    2.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9036   -2.7029    3.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5763   -1.1230    2.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7129   -2.6937    1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6855   -1.7206   -0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4340    0.3678   -0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7165    0.7566    2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4730    1.9829    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6518    2.1436    1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1642    0.4985    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0329    2.3351   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3635    2.9448   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3565    0.9457   -3.3941 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  1  0
  6  8  1  0
  8  9  2  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  1  0
 16 17  2  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
  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  6
  7 36  1  0
  8 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
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoate	ChEBI
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoate	ChEBI
(15S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid	ChEBI
(15S)-Hydroxyeicosa-(5Z,8Z,11Z,13E)-tetraenoic acid	ChEBI
(5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoic acid	ChEBI
(5Z,8Z,11Z,13E,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoic acid	ChEBI
(5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoic acid	ChEBI
15(S)-Hydroxyeicosatetraenoic acid	ChEBI
15S-HETE	ChEBI
Icomucret	ChEBI
15(S)-HETE	Kegg
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acid	Generator
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoic acid	Generator
(15S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate	Generator
(15S)-Hydroxyeicosa-(5Z,8Z,11Z,13E)-tetraenoate	Generator
(5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoate	Generator
(5Z,8Z,11Z,13E,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoate	Generator
(5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoate	Generator
15(S)-Hydroxyeicosatetraenoate	Generator
15-Hydroxy-5,8,11,13-eicosatetraenoic acid	HMDB
15-Hydroxy-5,8,11,13-eicosatetraenoic acid, (S-(e,Z,Z,Z))-isomer	HMDB
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosic acid	HMDB
(15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoate	HMDB
(15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoic acid	HMDB
(S)-15-HETE	HMDB
15 Hete	HMDB
15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate	HMDB
15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid	HMDB
15S-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoate	HMDB
15S-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid	HMDB
(5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosatetraenoic acid	HMDB
15(S)-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acid	HMDB
15(S)-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid	HMDB
15-Hydroxyeicosatetraenoic acid	HMDB
15S-Hydroxy-5,8,11,13-(Z,Z,Z,e)-eicosatetraenoic acid	HMDB
FA(20:4(5Z,8Z,11Z,13E,15-OH))	HMDB
FA(20:4(5Z,8Z,11Z,13E,15S-OH))	HMDB
15-HETE	HMDB, MeSH

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid

Traditional Name

15 hete

CAS Registry Number

54845-95-3

SMILES

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

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1

InChI Key

JSFATNQSLKRBCI-VAEKSGALSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroxyeicosatetraenoic 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

(5Z,8Z,11Z,13E)-15-HETE (CHEBI:15558 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C04742 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060001 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 3432563)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0003876)

Organ

Placenta (HMDB: HMDB0003876)

Excreta

Biofluid or Excreta

Urine (PMID: 8825400)

Cellular substructure

Extracellular (HMDB: HMDB0003876)
Membrane (HMDB: HMDB0003876)

Source

Exogenous

Exogenous (HMDB: HMDB0003876)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Endogenous

Endogenous (HMDB: HMDB0003876)

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

Industrial application

Pharmaceutical industry

Biomarker

Zellweger Syndrome (MarkerDB: MDB00000433)

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	4.405	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	5.82	ALOGPS
logP	5.36	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-1.6	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	14	ChemAxon
Refractivity	101.47 m³·mol⁻¹	ChemAxon
Polarizability	38.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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]+	187.377	31661259
DarkChem	[M-H]-	187.492	31661259
DeepCCS	[M+H]+	190.576	30932474
DeepCCS	[M-H]-	188.218	30932474
DeepCCS	[M-2H]-	221.104	30932474
DeepCCS	[M+Na]+	196.669	30932474
AllCCS	[M+H]+	186.8	32859911
AllCCS	[M+H-H2O]+	183.9	32859911
AllCCS	[M+NH4]+	189.5	32859911
AllCCS	[M+Na]+	190.3	32859911
AllCCS	[M-H]-	185.7	32859911
AllCCS	[M+Na-2H]-	187.5	32859911
AllCCS	[M+HCOO]-	189.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	7.03 minutes	32390414
Predicted by Siyang on May 30, 2022	22.0402 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.01 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3104.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	456.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	207.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	296.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	639.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1034.7 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	569.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2103.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	697.8 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	1762.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	753.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	502.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	329.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	503.8 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
15-HETE	CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O	4190.4	Standard polar	33892256
15-HETE	CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O	2385.7	Standard non polar	33892256
15-HETE	CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O	2587.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
15-HETE,1TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2736.5	Semi standard non polar	33892256
15-HETE,1TMS,isomer #2	CCCCC[C@H](O)/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2634.4	Semi standard non polar	33892256
15-HETE,2TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2711.7	Semi standard non polar	33892256
15-HETE,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2978.6	Semi standard non polar	33892256
15-HETE,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2876.5	Semi standard non polar	33892256
15-HETE,2TBDMS,isomer #1	CCCCC[C@@H](/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	3200.4	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 - 15-HETE GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zml-8392000000-2392d150cc271ce3a20a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15-HETE GC-MS (2 TMS) - 70eV, Positive	splash10-00bc-9224200000-28bb287a1a8aa8319f91	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15-HETE 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 - 15-HETE LC-ESI-QIT , negative-QTOF	splash10-014i-0269000000-6b7e052cfd2bb97562de	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOF	splash10-0ldi-0398000000-ff190e7ef4788dc235b4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOF	splash10-0pvi-0395000000-5aefff1d8848add1df10	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOF	splash10-0pdi-0693000000-f4fd2c47e2e2d4e7686c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOF	splash10-004i-1591000000-9d6de8ee88a3df3306d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOF	splash10-004i-0920000000-2023bab46b9a229c4bcf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOF	splash10-0002-3900000000-133a226bf0eb8235ecec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOF	splash10-052g-3900000000-084e1bd7da1469eba9c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 15-HETE LC-ESI-QIT , negative-QTOF	splash10-0aq9-5900000000-3d240e182d4edd31c981	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 10V, Positive-QTOF	splash10-0uk9-0059000000-c05583912116817f993d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 20V, Positive-QTOF	splash10-0r99-5393000000-12d4bc503332183deaa1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 40V, Positive-QTOF	splash10-0ab9-9740000000-536a9943ef814b845ee2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 10V, Negative-QTOF	splash10-014i-0019000000-c73882d7441506b152ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 20V, Negative-QTOF	splash10-014i-2169000000-bf33f63d6dfd38c0babf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 40V, Negative-QTOF	splash10-0a4l-9130000000-9448e55ece175750c0fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 10V, Positive-QTOF	splash10-0udi-0459000000-f09ca4984311e7651353	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 20V, Positive-QTOF	splash10-0f79-1973000000-22e0f4adf8c461582eab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 40V, Positive-QTOF	splash10-015c-9710000000-f42bad5d652833e0ca31	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 10V, Negative-QTOF	splash10-0gb9-0009000000-f96c871128e9efc2ab45	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 20V, Negative-QTOF	splash10-0uxr-1249000000-87b24140b02466ab64c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-HETE 40V, Negative-QTOF	splash10-052f-9130000000-3363d939385a8427ba5e	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Placenta

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	0.07 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	3432563	details
Blood	Detected and Quantified	0.00243 +/- 0.00148 uM	Adult (>18 years old)	Both	Normal	18953024	details
Blood	Detected and Quantified	0.02 +/- 0.01 uM	Adult (>18 years old)	Both	Normal	3432563	details
Blood	Detected and Quantified	1.12 +/- 0.42 uM	Adult (>18 years old)	Both	Normal	3432563	details
Blood	Detected and Quantified	0.0008 +/- 0.000023 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.0018 +/- 0.000098 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.00204 +/- 0.0012 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00048 +/- 0.00024 uM	Adult (>18 years old)	Both	Normal	John W. Newman, U...	details
Urine	Detected and Quantified	0-1.560e-08 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8825400	details
Urine	Detected and Quantified	0-0.00000001560 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8825400	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.000008113 (0.000005305-0.00001123) umol/mmol creatinine	Infant (0-1 year old)	Both	Zellweger syndrome	8825400	details

Associated Disorders and Diseases

Disease References

Peroxisomal biogenesis defect
Mayatepek E, Lehmann WD: 12- and 15-hydroxyeicosatetraenoic acid are excreted in the urine of peroxisome-deficient patients: evidence for peroxisomal metabolism in vivo. Pediatr Res. 1996 Jan;39(1):146-9. [PubMed:8825400 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.

Associated OMIM IDs

214100 (Peroxisomal biogenesis defect)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023242

KNApSAcK ID

Not Available

Chemspider ID

4444307

KEGG Compound ID

C04742

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280724

PDB ID

Not Available

ChEBI ID

15558

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000433

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Fogh K, Kragballe K: Eicosanoids in inflammatory skin diseases. Prostaglandins Other Lipid Mediat. 2000 Nov;63(1-2):43-54. [PubMed:11104340 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Glutathione peroxidase 7

General function:: Involved in glutathione peroxidase activity
Specific function:: It protects esophageal epithelia from hydrogen peroxide-induced oxidative stress. It suppresses acidic bile acid-induced reactive oxigen species (ROS) and protects against oxidative DNA damage and double-strand breaks.
Gene Name:: GPX7
Uniprot ID:: Q96SL4
Molecular weight:: 20995.88

Reactions

Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Water	details

Enzyme Details

2. Epididymal secretory glutathione peroxidase

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione. May constitute a glutathione peroxidase-like protective system against peroxide damage in sperm membrane lipids.
Gene Name:: GPX5
Uniprot ID:: O75715
Molecular weight:: 25202.14

Reactions

Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Water	details

Enzyme Details

3. Glutathione peroxidase 6

General function:: Involved in glutathione peroxidase activity
Specific function:: Not Available
Gene Name:: GPX6
Uniprot ID:: P59796
Molecular weight:: 24970.46

Reactions

Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Water	details

Enzyme Details

4. Glutathione peroxidase 1

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects the hemoglobin in erythrocytes from oxidative breakdown.
Gene Name:: GPX1
Uniprot ID:: P07203
Molecular weight:: 22087.94

Reactions

Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Water	details

Enzyme Details

5. Phospholipid hydroperoxide glutathione peroxidase, mitochondrial

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects cells against membrane lipid peroxidation and cell death. Required for normal sperm development and male fertility. Could play a major role in protecting mammals from the toxicity of ingested lipid hydroperoxides. Essential for embryonic development. Protects from radiation and oxidative damage (By similarity).
Gene Name:: GPX4
Uniprot ID:: P36969
Molecular weight:: 25046.57

Enzyme Details

6. Glutathione peroxidase 3

General function:: Involved in glutathione peroxidase activity
Specific function:: Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione.
Gene Name:: GPX3
Uniprot ID:: P22352
Molecular weight:: 25552.185

Reactions

Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Water	details

Enzyme Details

7. Glutathione peroxidase 2

General function:: Involved in glutathione peroxidase activity
Specific function:: Could play a major role in protecting mammals from the toxicity of ingested organic hydroperoxides. Tert-butyl hydroperoxide, cumene hydroperoxide and linoleic acid hydroperoxide but not phosphatidycholine hydroperoxide, can act as acceptors.
Gene Name:: GPX2
Uniprot ID:: P18283
Molecular weight:: 21953.835

Reactions

Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Water	details

Showing metabocard for 15-HETE (HMDB0003876)

MOL for HMDB0003876 (15-HETE)

3D MOL for HMDB0003876 (15-HETE)

3D SDF for HMDB0003876 (15-HETE)

3D-SDF for HMDB0003876 (15-HETE)

PDB for HMDB0003876 (15-HETE)

3D PDB for HMDB0003876 (15-HETE)

SMILES for HMDB0003876 (15-HETE)

INCHI for HMDB0003876 (15-HETE)

Structure for HMDB0003876 (15-HETE)

3D Structure for HMDB0003876 (15-HETE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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