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5-Oxo-ETE

PubChem CID
5283159
Structure
5-Oxo-ETE_small.png
5-Oxo-ETE_3D_Structure.png
Molecular Formula
Synonyms
  • 5-Oxo-ETE
  • 106154-18-1
  • 5-Oxoete
  • 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid
  • (6E,8Z,11Z,14Z)-5-Oxoicosa-6,8,11,14-tetraenoic acid
Molecular Weight
318.4 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2006-01-13
  • Modify:
    2025-01-18
Description
5-oxo-ETE is an oxoicosatetraenoic acid having a 5-oxo group; and (6E)-, (8Z), (11Z)- and (14Z)-double bonds. It has a role as a human metabolite, a mouse metabolite and an immunomodulator. It is functionally related to an icosa-6,8,11,14-tetraenoic acid. It is a conjugate acid of a 5-oxo-ETE(1-).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
5-Oxo-ETE.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6E,8Z,11Z,14Z)-5-oxoicosa-6,8,11,14-tetraenoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

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+
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

MEASLHGILYBXFO-XTDASVJISA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CCCCC/C=C\C/C=C\C/C=C\C=C\C(=O)CCCC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C20H30O3
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

126432-17-5

2.3.2 ChEBI ID

2.3.3 ChEMBL ID

2.3.4 HMDB ID

2.3.5 KEGG ID

2.3.6 Lipid Maps ID (LM_ID)

2.3.7 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 Wikidata

2.3.10 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5-oxo-eicosatetraenoic acid
  • 5-oxo-ETE

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
318.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
5.1
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
14
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
318.21949481 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
318.21949481 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
54.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
428
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.3 Chemical Classes

3.3.1 Lipids

Fatty Acyls [FA] -> Eicosanoids [FA03] -> Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 7
View All
Spectra ID
Instrument Type
LC-ESI-QIT
Ionization Mode
negative
Top 5 Peaks

317.141 100

273.256 4.81

299.277 3.46

203.22 2

255.271 1.65

Thumbnail
Thumbnail
Notes
instrument=4000Q TRAP, Applied Biosystems
2 of 7
View All
Spectra ID
Instrument Type
LC-ESI-QIT
Ionization Mode
negative
Top 5 Peaks

317.14 100

273.276 5.41

299.238 4.64

203.214 2.81

255.272 2.28

Thumbnail
Thumbnail
Notes
instrument=4000Q TRAP, Applied Biosystems

4.1.2 LC-MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
317.21221882
Instrument
4000Q TRAP, Applied Biosystems
Instrument Type
LC-ESI-QIT
Ionization
ESI
Ionization Mode
negative
Collision Energy
50 V
Top 5 Peaks

161.120 100

245.120 100

203.120 50

161.280 33.33

95.040 33.33

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
317.21221882000003
Instrument
4000Q TRAP, Applied Biosystems
Instrument Type
LC-ESI-QIT
Ionization
ESI
Ionization Mode
negative
Collision Energy
45 V
Top 5 Peaks

203.139 100

317.200 45.65

109.027 21.74

245.120 10.87

133.040 10.87

Thumbnail
Thumbnail
License
CC BY-NC-SA

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Human Metabolite Information

7.1.1 Cellular Locations

Membrane

7.1.2 Metabolite Pathways

7.2 Biochemical Reactions

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Chemical Co-Occurrences in Literature

8.4 Chemical-Gene Co-Occurrences in Literature

8.5 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

9.3 Chemical Co-Occurrences in Patents

9.4 Chemical-Disease Co-Occurrences in Patents

9.5 Chemical-Gene Co-Occurrences in Patents

10 Interactions and Pathways

10.1 Chemical-Target Interactions

10.2 Pathways

11 Biological Test Results

11.1 BioAssay Results

12 Taxonomy

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 LIPID MAPS Classification

13.4 KEGG: Lipid

13.5 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

13.6 ChEMBL Target Tree

13.7 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  3. ChEBI
  4. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  5. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    5-Oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid
    http://www.nist.gov/srd/nist1a.cfm
  6. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  7. Therapeutic Target Database (TTD)
  8. Japan Chemical Substance Dictionary (Nikkaji)
  9. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  10. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  11. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  12. Metabolomics Workbench
  13. Natural Product Activity and Species Source (NPASS)
  14. Wikidata
    5-oxo-eicosatetraenoic acid
    https://www.wikidata.org/wiki/Q25323762
  15. Wikipedia
  16. PubChem
  17. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  18. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  19. PATENTSCOPE (WIPO)
  20. NCBI
CONTENTS