Lipoxin A4 - Moligand™, ≥95%, 100µg/ml in ethanol , Agonist of FPR2/ALX;Agonist of FPR3;Agonist of GPR32, CAS No.89663-86-5, Agonist of FPR2/ALX;Agonist of FPR3;Agonist of GPR32

CAS: 89663-86-5 Cat. No.: L345922 Formule: C₂₀H₃₂O₅ Poids moléculaire: 352.47 Numéro CE: 200-578-6

GRADE & PURITY Moligand™, ≥95%, 100µg/ml in ethanol

Synonyms

(7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoate | GTPL1034 | 7,9,11,13-Eicosatetraenoic acid, 5,6,15-trihydroxy-, (5S,6R,7E,9E,11Z,13E,15S)- | F7C6J3D79J | NCGC00161280-03 | (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyeicosa-7,9,11

Storage

Argon charged,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Vue d’ensemble

Lipoxin A4 (LXA4), an endogenous lipoxygenase-derived eicosanoid mediator, has potent dual pro-resolving and anti-inflammatory properties. Lipoxin A4 inhibits proliferation and inflammatory cytokine/chemokine production of human epidermal keratinocytes (NHEKs) associated with the ERK1/2 and NF-kB pathways. Lipoxin A4 inhibits serum amyloid A (SAA)-mediated IL-8 release with an IC50 value of 25.74 nM.

Specifications

Synonymes

(7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoate | GTPL1034 | 7,9,11,13-Eicosatetraenoic acid, 5,6,15-trihydroxy-, (5S,6R,7E,9E,11Z,13E,15S)- | F7C6J3D79J | NCGC00161280-03 | (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyeicosa-7,9,11

Spécifications et pureté

Moligand™, ≥95%, 100µg/ml in ethanol

Mécanismes biochimiques et physiologiques

Lipoprotein A4 (LXA4) is synthesized from arachidonic acid and is an endogenous lipoxygenase derived arachidonic acid mediator. It is an effective activator of human protein kinase C. It inhibits the cytotoxicity of natural killer cells. LXA4 regulates th

Conditions de stockage de stockage

Argon charged,Store at -80°C

Expédié en

Dry ice packs + Cold packs

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Grade

Moligand™

Type d'action

AGONIST

Mécanisme d'action

Agonist of FPR2/ALX;Agonist of FPR3;Agonist of GPR32

Note

Store as supplied at -80° C for up to 1 year.

Pureté

≥95%

Propriétés du produit

• pKa: pKa: 4.67

Noms et identifiants

• Sourires canoniques: CCCCCC(C=CC=CC=CC=CC(C(CCCC(=O)O)O)O)O
• IUPAC Name: (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid
• InChIKey: IXAQOQZEOGMIQS-SSQFXEBMSA-N
• 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
• Isomères SMILES: CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)O)O
• WGK Allemagne: 2
• Poids moléculaire: 352.47
• Reaxy-Rn: 34893640
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=34893640&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Eicosanoids
        • Level5 Hydroxyeicosatetraenoic acids
          • Level6 Lipoxins

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Eicosanoids
• Intermediate Tree Nodes: Hydroxyeicosatetraenoic acids
• Direct Parent: Lipoxins
• Alternative Parents: Long-chain fatty acids Hydroxy fatty acids Unsaturated fatty acids Secondary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Lipoxin - Long-chain fatty acid - Hydroxy fatty acid - Fatty acid - Unsaturated fatty acid - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Polyol - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Carbonyl group - Organooxygen compound - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as lipoxins. These are eicosanoids with a trihydroxyicosatetraenoic acid skeleton (a c20-fatty acid, with the chain bearing three hydroxyl groups and four double bonds). Lipoxins have four double bonds, which are all conjugated. In some cases a hydroxyl group is substituted by a C=O group.
• External Descriptors: Lipoxins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Cibles associées (humaines)

GPR32 Tchem Probable G-protein coupled receptor 32 (1 Activities)

Discover Target: GPR32

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FPR2 Tchem N-formyl peptide receptor 2 (7 Activities)

Discover Target: FPR2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FPR3 Tchem N-formyl peptide receptor 3 (1 Activities)

Discover Target: FPR3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

THP-1 (11052 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK293 (82097 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FPR2 Tchem Lipoxin A4 receptor (3472 Activities)

Discover Target: FPR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NFKB2 Tchem Nuclear factor NF-kappa-B complex (2307 Activities)

Discover Target: NFKB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cibles associées (non humaines)

Mus musculus (284745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mécanismes d'action

Propriétés chimiques et physiques

• Solubilité: Soluble in ethanol, DMSO (≥50 mg/ml), DMF (≥50 mg/ml), and PBS (pH 7.2) (≥1 mg/ml).
• Indice de réfraction: n20D1.54
• Point d'ébullition (°C): 78° C
• Poids moléculaire: 352.500 g/mol
• XLogP3: 3.100
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 352.225 Da
• Monoisotopic Mass: 352.225 Da
• Topological Polar Surface Area: 98.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 451.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 4
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 4
• Covalently-Bonded Unit Count: 1

Références

1. Ding Peng-Fei, Zhang Jia-Tong, Zhu Xiao-Long, Cui Yue, Chen Chun-Lei, Liu Xun-Zhi, Shen Jun-Da, Zou Le-Xuan, Lu Yue, Zhuang Zong, Hang Chun-Hua, Li Wei.  (2025)  P2X7-CaMKII drives 5-LOX nuclear translocation to impair microglial function after subarachnoid hemorrhage.  Journal of Neuroinflammation,  22  (1): (1-16).  [PMID:40877894] [10.1186/s12974-025-03530-3]