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From the body

LXA4Lipoxin A4

An endogenous pro-resolving eicosanoid, described in 2012 as a positive allosteric modulator of CB1; the finding is debated.

Endogenous
Level of detail

C₂₀H₃₂O₅

CAS 89663-86-5

Family
Endocannabinoid or related mediatorPutative
Molar mass
352.50 g/mol

Updated on

In plain terms

Lipoxin A4 is a small fatty molecule that the human body makes itself from arachidonic acid. Researchers class it among the so-called « pro-resolving » mediators, which act at the end of an inflammatory reaction. It does not come from hemp; a 2012 study in mice showed that it strengthened the action of anandamide at the CB1 receptor, a result another laboratory did not find.

Receptors and activity

Target network

CB1Positive allosteric modulatorOrthosteric Ki > 10 µM (maximal displacement of 40% of [3H]SR141716A, mouse brain membranes); in the presence of LXA4, the anandamide IC50 at the high-affinity site shifts from 17 to 2 nM (Pamplona 2012); no potentiation in autaptic neurons, rather a NAM profile (Straiker 2015)
  • Activates

The lower the cited value, the closer the target sits to LXA4: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of LXA4.

Brain, side view
Body, front view
Blood

CB1CB1 found in 7 regions of the body

  1. Basal gangliadenseMost dense in basal ganglia outflow nuclei1
  2. CerebellumdenseVery dense in the cerebellum1
  3. HippocampusdenseVery high concentrations in the hippocampus2
  4. AmygdaladenseHigh concentrations in the amygdala2
  5. CortexpresentPresent throughout the neocortex2
  6. Adipose tissuepresentExpressed in adipose tissue3
  7. GutpresentColonic epithelium, smooth muscle and plexus4

Map sources

  1. Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
  2. Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
  3. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  4. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)

Cited values

  1. ALX/FPR2AgonistKd = 1.7 nM · human79 out of 100

    Fiore et al. 1994, J Exp Med (new tab) · specific [3H]LXA4 binding, CHO cells transfected with the pINF114 cDNA (ALX); Kd 0.5 to 0.7 nM on human neutrophils

  2. CB1Positive allosteric modulatorno measured value cited

    Orthosteric Ki > 10 µM (maximal displacement of 40% of [3H]SR141716A, mouse brain membranes); in the presence of LXA4, the anandamide IC50 at the high-affinity site shifts from 17 to 2 nM (Pamplona 2012); no potentiation in autaptic neurons, rather a NAM profile (Straiker 2015)

Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Pharmacology

Described in 1984 in human leukocytes (Serhan 1984), lipoxin A4 belongs to the so-called pro-resolving lipid mediators; its own receptor is ALX/FPR2, which it activates at nanomolar concentrations (Fiore 1994; Chiang 2006). The link with the endocannabinoid system rests on a 2012 PNAS study: detected in brain tissue, lipoxin A4 did not occupy the orthosteric site of CB1 (Ki > 10 µM) but increased the affinity of anandamide for this receptor (IC50 from 17 to 2 nM at the high-affinity site), without altering endocannabinoid metabolism; it potentiated anandamide-induced catalepsy but not that of 2-AG, and a CB1-dependent effect was observed against a spatial memory deficit induced by the β-amyloid peptide in mice (Pamplona 2012). A commentary in the same issue called it an « allosteric endocannabinoid » (Pertwee 2012). The result was not reproduced in autaptic hippocampal neurons whose signalling relies on 2-AG: at 1 µM, lipoxin A4 produced no potentiation, with a profile the authors consider closer to a negative modulator (Straiker 2015). Its status as a positive allosteric modulator of CB1 therefore remains debated; no human data exist on this cannabinoid side.

Key sources.

History

Source
An endogenous molecule, absent from cannabis and from any plant. It is produced by the body's cells, human and animal, during inflammatory reactions, often through interactions between two cell types (Serhan 2005).

Biosynthetic pathway

In vivo

Formed from arachidonic acid by the successive action of lipoxygenases, in particular through the interaction of the 5-lipoxygenase and 15-lipoxygenase pathways of leukocytes (Serhan 1984). This biosynthesis is often shared between two cell types (transcellular biosynthesis). Aspirin also triggers the formation of endogenous epimers, the 15-epi-lipoxins (Serhan 2005).

Classification

Family, origin and source verification

Family

Endocannabinoid or related mediator › Putative

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

No dedicated article.

References

  1. Pamplona et al. 2012, PNAS: positive allosteric modulator of CB1 (new tab)PMID 23150578
  2. Pertwee 2012, PNAS: commentary « allosteric endocannabinoid » (new tab)PMID 23204441
  3. Straiker et al. 2015, Pharmacol Res: CB1 allosteric modulators in autaptic neurons (new tab)PMID 26211948
  4. Serhan, Hamberg & Samuelsson 1984, PNAS: discovery and naming of the lipoxins (new tab)PMID 6089195
  5. Fiore et al. 1994, J Exp Med: cloning of the high-affinity LXA4 receptor (new tab)PMID 8006586
  6. Clish et al. 2000, J Biol Chem: metabolic inactivation of LXA4 (new tab)PMID 10837478
  7. Wu et al. 2013, Br J Dermatol: topical 15(R/S)-methyl-LXA4 in the infant (new tab)PMID 22834636
  8. ChEBI:6498, lipoxin A4 (new tab)
  9. PubChem CID 5280914, Lipoxin A4 (new tab)

Identifiers

Names

Common name
Lipoxin A4
IUPAC name
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid
Other names
LXA4

Identifiers

Formula
C₂₀H₃₂O₅
CAS
89663-86-5
PubChem CID
5280914(new tab)
ChEBI
CHEBI:6498(new tab)
InChIKey
IXAQOQZEOGMIQS-SSQFXEBMSA-N
SMILES
CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)O)O

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.