15(R)-Lipoxin A4 - Moligand™, ≥95%, ~100ug/ml in ethanol , Agonist of FPR2/ALX, CAS No.171030-11-8, Agonist of FPR2/ALX

CAS: 171030-11-8 Cat. No.: L342353 Molecular Weight: 352.5

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

Synonyms

GTPL3933 | (5S,6R,7E,9E,11Z,13E,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid | AKOS040755721 | aspirin triggered 15-epi lipoxin A4 | Q27074548 | AT-Lipoxin A4 | SCHEMBL1691709 | LMFA03040010 | Lipoxin A4, 15-epi | 15-epi-LXA4 | aspirin-triggered

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Lipoxin A4, 15-epi is an epimeric lipoxin A4 (catalog number sc-201060) analog that is more potent and metabolically stable than LXA4. Has been shown to exhibit anti-inflammatory properties and serves as a "stop signal" to excessive leukocyte tafficking/infiltration. Lipoxin A4, 15-epi blocks TNF-a-induced IL-8 release in human enterocyte. It is also an important modulator of the many pharmacological actions caused by aspirin.

Specifications

Synonyms

GTPL3933 | (5S, 6R, 7E, 9E, 11Z, 13E, 15R)-5, 6, 15-trihydroxyicosa-7, 9, 11, 13-tetraenoic acid | AKOS040755721 | aspirin triggered 15-epi lipoxin A4 | Q27074548 | AT-Lipoxin A4 | SCHEMBL1691709 | LMFA03040010 | Lipoxin A4, 15-epi | 15-epi-LXA4 | aspirin-triggered

Specifications & Purity

Moligand™, ≥95%, ~100ug/ml in ethanol

Storage

Protected from light, Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of FPR2/ALX

Purity

≥95%

Product Properties

• pKa: pKₐ: 4.67 (Predicted)

Names and Identifiers

• Canonical Smiles: CCCCCC(C=CC=CC=CC=CC(C(CCCC(=O)O)O)O)O
• IUPAC Name: (5S,6R,7E,9E,11Z,13E,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid
• InChIKey: IXAQOQZEOGMIQS-JEWNPAEBSA-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+/m1/s1
• Isomeric SMILES: CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)O)O
• Alternate CAS: 171030-11-8
• 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
• Molecular Weight: 352.5
• 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
    • Class Fatty Acyls
      • Subclass Eicosanoids
        • Level5 Hydroxyeicosatetraenoic acids
          • Level6 Lipoxins

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: 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: long-chain fatty acid - polyunsaturated fatty acid - hydroxy fatty acid - lipoxin

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

Associated Targets(Human)

FPR2 Tchem N-formyl peptide receptor 2 (0 Activities)

Discover Target: FPR2

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO (~50 mg/ml), DMF (~50 mg/ml), and PBS pH 7.2 (~1 mg/ml).
• Sensitivity: Light sensitive
• Refractive Index: n20D~1.54 (Predicted)
• Boil Point(°C): 78° C
• Molecular Weight: 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