Details of the Drug

General Information of Drug (ID: DMGSVL0)

Drug Name

LXA4

Synonyms

Lipoxin A4; lipoxin A4; 5S,6R-LipoxinA4; 89663-86-5; 5S,6R,15S-trihydroxy-7E,9E,11Z,13E-Eicosatetraenoic acid; CHEBI:6498; (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid; (7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoic acid; (5S,6R,15S)-Trihydroxy-(7E,9E,11Z,13E)-Eicosatetraenoic acid; Lipoxin A; 5,6,15-trihydroxy-7,9,11,13-eicosatetraenoic acid; 5,6,15-triHETE; 5S,6S-Lipoxin A4; AC1NQXRP; BSPBio_001378; 6R-LXA4; Lipoxin A4, ethanol solution; GTPL1034; BML1-E11; CHEMBL392438; 5,6,15-triHETE ; [3H]LXA4

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

352.5

Logarithm of the Partition Coefficient (xlogp)

3.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C20H32O5
IUPAC Name: (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid
Canonical 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

Cross-matching ID

PubChem CID: 5280914
ChEBI ID: CHEBI:6498
CAS Number: 89663-86-5
TTD ID: D0R1FZ

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
FMLP-related receptor I (FPR2)	TTOJ1NF	FPR2_HUMAN	Agonist	[2]
G-protein coupled receptor 32 (GPR32)	TT7OCUB	GPR32_HUMAN	Agonist	[2]
N-formyl peptide receptor 3 (FPR3)	TT16TM5	FPR3_HUMAN	Agonist	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Intercellular adhesion molecule 1 (ICAM1)	OTTOIX77	ICAM1_HUMAN	Drug Response	[4]
Interleukin-1 beta (IL1B)	OT0DWXXB	IL1B_HUMAN	Gene/Protein Processing	[5]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[5]
P-selectin (SELP)	OTWR90PK	LYAM3_HUMAN	Drug Response	[4]
Platelet-derived growth factor receptor beta (PDGFRB)	OTYSNK9Q	PGFRB_HUMAN	Post-Translational Modifications	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3411).
2	Resolvin D1 binds human phagocytes with evidence for proresolving receptors. Proc Natl Acad Sci U S A. 2010 Jan 26;107(4):1660-5.
3	Aspirin-triggered 15-epi-lipoxin A4 (LXA4) and LXA4 stable analogues are potent inhibitors of acute inflammation: evidence for anti-inflammatory receptors. J Exp Med. 1997 May 5;185(9):1693-704.
4	Mechanisms for lipoxin A4-induced neutrophil-dependent cytotoxicity for human endothelial cells. J Lab Clin Med. 1995 Jul;126(1):36-43.
5	Aspirin-triggered lipoxin enhances macrophage phagocytosis of bacteria while inhibiting inflammatory cytokine production. Am J Physiol Gastrointest Liver Physiol. 2011 Sep;301(3):G487-97. doi: 10.1152/ajpgi.00042.2011. Epub 2011 Jun 9.
6	Aspirin-triggered lipoxin and resolvin E1 modulate vascular smooth muscle phenotype and correlate with peripheral atherosclerosis. Am J Pathol. 2010 Oct;177(4):2116-23. doi: 10.2353/ajpath.2010.091082. Epub 2010 Aug 13.