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Lipoxin A4

PubChem CID
5280914
Structure
Lipoxin A4_small.png
Lipoxin A4_3D_Structure.png
Molecular Formula
Synonyms
  • lipoxin A4
  • 89663-86-5
  • LXA4
  • 5S,6R-LipoxinA4
  • Lipoxin A
Molecular Weight
352.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-18
Description
Lipoxin A4 is a C20 hydroxy fatty acid having (5S)-, (6R)- and (15S)-hydroxy groups as well as (7E)- (9E)-, (11Z)- and (13E)-double bonds. It has a role as a metabolite and a human metabolite. It is a lipoxin, a long-chain fatty acid and a hydroxy polyunsaturated fatty acid. It is a conjugate acid of a lipoxin A4(1-).
lipoxin A4 has been reported in Homo sapiens with data available.
Lipoxin A4 is a hydroxy polyunsaturated fatty acid that is a metabolite of arachidonic acid, with potential anti-inflammatory, antifibrinolytic and analgesic activities.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Lipoxin A4.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

IXAQOQZEOGMIQS-SSQFXEBMSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

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

2.2 Molecular Formula

C20H32O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

94292-81-6

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG ID

2.3.9 Lipid Maps ID (LM_ID)

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 15-epi-lipoxin A4
  • 15-epi-LXA4
  • 5,6,15-tri-HETE
  • 5,6,15-triHETE
  • 5,6,15-trihydroxy-7,9,11,13-eicosatetraenoic acid
  • lipoxin A4
  • LXA4

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
352.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
3.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
14
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
352.22497412 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
352.22497412 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
98 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
25
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
451
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
3
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

3.2.2 Collision Cross Section

197.89 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

194 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

193.3 Ų [M-H]-

196.6 Ų [M+Na]+

S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.3 Chemical Classes

3.3.1 Lipids

Fatty Acyls [FA] -> Eicosanoids [FA03] -> Lipoxins [FA0304]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 2
Spectra ID
Instrument Type
LC-ESI-QQ
Ionization Mode
negative
Top 5 Peaks

351.2 100

235.1 65.96

114.9 49.94

216.9 35.55

115.5 23.53

Thumbnail
Thumbnail
Notes
instrument=TSQ Vantage, Thermo Scientific coupled to Nexera, Shimadzu
2 of 2
Spectra ID
Instrument Type
LC-ESI-QQ
Ionization Mode
negative
Top 5 Peaks

356.1 100

240.2 73.79

222.2 68.99

115.0 68.37

115.5 28.97

Thumbnail
Thumbnail
Notes
instrument=TSQ Vantage, Thermo Scientific coupled to Nexera, Shimadzu

4.1.2 LC-MS

1 of 13
View All
Authors
Nakanishi H, Taguchi R, Graduate School of Medicine, The University of Tokyo
Instrument
4000Q TRAP, Applied Biosystems
Instrument Type
LC-ESI-QIT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
20 V
Precursor Adduct
[M-H]-
Top 5 Peaks

351.126 999

217.199 415

235.193 283

115.04 125

289.236 100

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 13
View All
Authors
Nakanishi H, Taguchi R, Graduate School of Medicine, The University of Tokyo
Instrument
4000Q TRAP, Applied Biosystems
Instrument Type
LC-ESI-QIT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
25 V
Precursor Adduct
[M-H]-
Top 5 Peaks

217.156 999

351.136 342

235.162 323

115.021 169

271.173 166

Thumbnail
Thumbnail
License
CC BY-NC-SA

6 Chemical Vendors

7 Drug and Medication Information

7.1 Biomarker Information

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

8.2 Human Metabolite Information

8.2.1 Tissue Locations

  • Leukocyte
  • Platelet

8.2.2 Cellular Locations

  • Extracellular
  • Membrane

8.3 Biochemical Reactions

9 Associated Disorders and Diseases

Disease
Coronary artery disease
References

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Thieme References

10.5 Chemical Co-Occurrences in Literature

10.6 Chemical-Gene Co-Occurrences in Literature

10.7 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Chemical-Target Interactions

12.2 Pathways

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 LIPID MAPS Classification

15.4 KEGG: Lipid

15.5 ChemIDplus

15.6 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

15.7 ChEMBL Target Tree

15.8 NORMAN Suspect List Exchange Classification

15.9 CCSBase Classification

15.10 EPA DSSTox Classification

15.11 LOTUS Tree

15.12 MolGenie Organic Chemistry Ontology

16 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. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. 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
  6. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  7. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Lipoxin A4
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  8. ChEBI
  9. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  10. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  11. 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
  12. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  13. 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
  14. Therapeutic Target Database (TTD)
  15. Japan Chemical Substance Dictionary (Nikkaji)
  16. 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
  17. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  18. Natural Product Activity and Species Source (NPASS)
  19. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  20. MassBank Europe
  21. 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
  22. Metabolomics Workbench
  23. Springer Nature
  24. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  25. Wikidata
  26. PubChem
  27. 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
    Anti-Inflammatory Agents, Non-Steroidal
    https://www.ncbi.nlm.nih.gov/mesh/68000894
  28. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  29. PATENTSCOPE (WIPO)
  30. NCBI
CONTENTS