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Lipoxin A4

Athanor · official

C20H32O5 · 352.5 g/mol

IUPAC name: (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid

Also called LXA4, lipoxin, specialised pro-resolving mediator, SPM

Lipids
Open in Athanor
The structure of Lipoxin A4
Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid
Synonyms
LXA4, lipoxin, specialised pro-resolving mediator
+ 38 more

SPM, 5S,6R-LipoxinA4, (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid, 5,6,15-triHETE, 5S,6R,15S-trihydroxy-7E,9E,11Z,13E-Eicosatetraenoic acid, CHEBI:6498, F7C6J3D79J, 6R-LXA4, DTXSID6040535, (7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoic acid, 5S,6R,15S-trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid, (5S,6R,15S)-trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid, 5(S),6(R),15(S)-trihydroxyeicosa-7E,9E,11Z,13E-tetraenoic acid, 5,6,15-trihydroxy-7,9,11,13-eicosatetraenoic acid, (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxy-7,9,11,13-eicosatetraenoic acid, (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyeicosa-7,9,11,13-tetraenoic acid, RefChem:153632, 5,6,15-tri-HETE, DTXCID201774355, (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoate, Lipoxin A, LIPOXINA4, 7,9,11,13-Eicosatetraenoicacid, 5,6,15-trihydroxy-, (5S,6R,7E,9E,11Z,13E,15S)-, LXA4-[19,19,20,20,20-d5], UNII-F7C6J3D79J, BSPBio_001378, LXA4; 5S,6R-LipoxinA4, 5(S),6(R)-Lipoxin A4, BML1-E11, CHEMBL392438, GTPL1034, orb1985086, SCHEMBL2384474, IXAQOQZEOGMIQS-SSQFXEBMSA-N, GLXC-22763, HMS1361E20, HMS1791E20, HMS1989E20

Molecular formula
C20H32O5
Empirical formula
C20H32O5
Molecular weight
352.5 g/mol
Exact mass
352.22497
CAS number
89663-86-5
PubChem CID
5280914
Canonical SMILES
CCCCCC(C=CC=CC=CC=CC(C(CCCC(=O)O)O)O)O
Isomeric SMILES
CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)O)O
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
InChIKey
IXAQOQZEOGMIQS-SSQFXEBMSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
25
Rings
0
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.55
H-bond donors
4
H-bond acceptors
4 computed here · PubChem 5
Rotatable bonds
14
TPSA (Ų)
98
Formal charge
0
XLogP3
3.1 PubChem
Complexity
451 PubChem
Stereocenters
3 definedCIP: C6: S · C16: R · C18: S
Double-bond geometry
C8=C9: E · C10=C11: Z · C12=C13: Z · C14=C15: E
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C68.15%
  • H9.15%
  • O22.70%

Isotope pattern

100%352.22522%353.2283.4%354.231355.234

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
3.13 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-3.07 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.95 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 352.47
  • log P ≤ 5 (Crippen): 3.13
  • H-bond donors ≤ 5: 4
  • H-bond acceptors ≤ 10: 4

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

No GHS hazard classification was found in the sources.

Safety data sheets on the supplier’s page: Sigma-Aldrich, AA BLOCKS, Alfa Chemistry.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  2. [2]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  4. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  5. ·Literature on PubChem

Data last updated 2026-10-14.