ATLa2   Click here for help

GtoPdb Ligand ID: 3383

Synonyms: ATL analog [15-epi-16-(para-fluoro)-phenoxy-LXA4]
Compound class: Synthetic organic
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 86.99
Molecular weight 404.2
XLogP 4
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC(=O)CCCC(C(C=CC=CC=CC=CC(COc1ccc(cc1)F)C)O)O
Isomeric SMILES OC(=O)CCC[C@@H]([C@@H](/C=C/C=C/C=C\C=C\[C@@H](COc1ccc(cc1)F)C)O)O
InChI InChI=1S/C23H29FO5/c1-18(17-29-20-15-13-19(24)14-16-20)9-6-4-2-3-5-7-10-21(25)22(26)11-8-12-23(27)28/h2-7,9-10,13-16,18,21-22,25-26H,8,11-12,17H2,1H3,(H,27,28)/b4-2-,5-3+,9-6+,10-7+/t18-,21+,22-/m0/s1
InChI Key SGFIFYSIHRWSCE-LLXPRBAESA-N
References
1. Clish CB, O'Brien JA, Gronert K, Stahl GL, Petasis NA, Serhan CN. (1999)
Local and systemic delivery of a stable aspirin-triggered lipoxin prevents neutrophil recruitment in vivo.
Proc Natl Acad Sci USA, 96 (14): 8247-52. [PMID:10393980]
2. Fiore S, Maddox JF, Perez HD, Serhan CN. (1994)
Identification of a human cDNA encoding a functional high affinity lipoxin A4 receptor.
J Exp Med, 180 (1): 253-60. [PMID:8006586]
3. Fiore S, Serhan CN. (1995)
Lipoxin A4 receptor activation is distinct from that of the formyl peptide receptor in myeloid cells: inhibition of CD11/18 expression by lipoxin A4-lipoxin A4 receptor interaction.
Biochemistry, 34 (51): 16678-86. [PMID:8527441]
4. Gronert K, Martinsson-Niskanen T, Ravasi S, Chiang N, Serhan CN. (2001)
Selectivity of recombinant human leukotriene D(4), leukotriene B(4), and lipoxin A(4) receptors with aspirin-triggered 15-epi-LXA(4) and regulation of vascular and inflammatory responses.
Am J Pathol, 158 (1): 3-9. [PMID:11141472]
5. Guilford WJ, Bauman JG, Skuballa W, Bauer S, Wei GP, Davey D, Schaefer C, Mallari C, Terkelsen J, Tseng JL et al.. (2004)
Novel 3-oxa lipoxin A4 analogues with enhanced chemical and metabolic stability have anti-inflammatory activity in vivo.
J Med Chem, 47 (8): 2157-65. [PMID:15056011]
6. Takano T, Fiore S, Maddox JF, Brady HR, Petasis NA, Serhan CN. (1997)
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, 185 (9): 1693-704. [PMID:9151906]